Unlonely with Dr. Jody Carrington - How Do You Know When To Cut Them Loose? - Dr. Jess O’Reilly

Episode Date: January 16, 2025

Loneliness doesn’t wait for an empty room—it finds us even in crowded spaces and close relationships. In this episode, Dr. Jody Carrington sits down with Dr. Jess O’Reilly, a Toronto-based sexologist (PhD), author and television personality, to explore why connection feels elusive in a hyper-connected world. From the myth of #CouplesGoals to the quiet ache of adult friendships, they dig into the layers of relationships, love, and loneliness. Jess shares why "quality over longevity" is the new mantra for relationships and how intentionality—not convenience—should guide who we let into our lives. With wisdom on everything from romantic partnerships to choosing your inner circle, this conversation is a call to reframe connection.Follow Dr. Jess O'Reilly:FacebookInstagramYouTubeWebsite Hosted on Acast. See acast.com/privacy for more information.

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schedules so you can snag these fabulous pieces at grocery stores across Canada or shop online from the comfort of your own home. And because I adore you all, here's a little gift. Use code JODY25 at checkout on joefresh.com for some sweet savings. So don't wait. Explore the new JoFresh Activewear collection at any JoFresh store or online at joefresh.com today. At the beginning of every episode, there will always be time for an acknowledgement. You know, the more we do this, people ask, why do you have to do the acknowledgement and every episode? I got to tell you, I've never been more grateful for being able to raise my babies on the land where so much sacrifice was made.

And I think what's really critical in this process is that the ask is just that we don't forget. So the importance of saying these words at the beginning of every episode will always be of utmost importance to me and this team. So everything that we created here today for you happened on Treaty 7 land, which is now known as the center part of the province of Alberta. It is home of the Blackfoot Confederacy, which

is made up of the Siksika, the Kainai, the Pikani, the Tatina First Nation, the Stony Nakoda First Nation, and the Métis Nation Region 3. Our job, our job as humans, is to simply acknowledge each other. That's how we do better, be better, and stay connected to the good. Well, hello, my fellow humans. Welcome back, I hope, or welcome in to the Unlonely Podcast. This episode, you're going to meet a remarkable woman named Dr. Jess O'Reilly. And Jess and I met a while back at an event where we spoke together. And I got to tell you, she blew me away. Her stage presence is phenomenal, but her ease, her comfort, her understanding

of human relationships, intimacy, made me rethink so many things. And I just knew that it took us a long time. She's all over the world speaking. She had a spot for a very long time on breakfast television in Toronto. And she's written a number of phenomenal books. She is known as a Toronto based sexologist. So she's got a PhD. She's an author.

And as I said, a TV personality. Um, she has worked with thousands of couples from all corners of the globe to transform their relationships because she has this wildly successful program that we talk a little bit about in the episode called marriage as a business. And I mean, listen, Prague, Istanbul, Albuquerque, New York, she's like, she's all over the place and it's, she's just so practical, no nonsense. Like, how the fuck do we stay connected in this world where we have no script for it? So, um, her doctoral research was all around sexual health and relationship education. And she's really such an advocate for classroom education, talking about sex. And as you'll see in this episode,

I am the most prudest human on the planet. Despite the fact that I'm like all over the place sometimes with my personality, when it comes to sex and intimacy, I'm like, and done. So mostly in this episode, I talk a lot about the depth of relationship, not sort of like how many orgasms you need to have or how often you're having sex. Jess talks about all those things, but we really took this whole hour to dive into, I think, the critical nature of really developing

the underpinnings of relationships, not only in your intimate relationships, but in your friendships where we tend to spend the most time, particularly with the people we work with. Do we develop friendships there? I mean, for a long time, it was like, you know, don't mix work and friendships. And I mean, for me, that's become impossible to do. And so how do you navigate friendships in this season? Because I think it's, we don't got a script for it. So she is now, she's got this beautiful contract with Tinder.

She's Tinder Canada's dating and relationship expert. Uh, she's a Canadian born, a Chinese, Jamaican and Irish by descent. Uh, I hope you love her as much as I do, because this, this conversation was part one and I, and I cannot wait to have her back for part two, so buckle up and I hope you love it. Okay. Listen, listen, my fellow humans, you better back up, buckle down, pony up. I don't, I don't know, but there's gotta be a really good term for this. I have none, none, none, none, none, never been as excited as I am today, uh, to

talk to my friend, Dr. Jess O'Reilly. Um, we spoke together at an event and I've just heard of her because honestly, I am the most outlandish conservative human on the planet. Marty gets often amazed at me because anytime anybody talks about sex, like I'm, I will like embarrass the shit out of anybody anytime I'm all like up in people's faces but you start talking about sexual relationships and intimacy and I'm like,

oh, oh, I can't, my kids just went through sex ed and like, it was the funniest part of my life because they were like, mom, did you know that want sometimes one ball can drop in the other camp? Anyways, the, the idea of having Jess in studio today is phenomenal. And she is Tinder Canada's dating and relationship expert. And she is so much more because this woman, what I love the most about her, she's the badass CEO of one of the most successful companies of all time.

And she's been such an expert in this space that people haven't talked about. And I am so excited to sit with you today, Dr. O'Reilly, because I think one of the things I want to know the best, most about from you is what are people, why, what is happening in this disconnected world? What do you see as you travel globally in this beautiful space?

Are we lonely? Are we disconnected? Well, first of all, all the positive feelings and admiration are mutual. So flowing right back to you, I like that there's a little bit, I mean, obviously you're brilliant on stage. I've seen you speak, you're highly articulate. And I love that there's just this tiny little bit of getting tongue tied around this topic

because I have some of that around certain topics too that you can probably help me with. But what are we seeing out there? What I see is that people are craving connection, but not really facilitating the space for it. So we're saying relationships matter. We're saying that we want to do these things, but we're not really following through. We're saying that we want to invest in our marriages. We're saying that we want to invest in our marriages. We're saying that we want to spend

more time with friends. But you know the kind of the joke, the meme of how do you get together with your friends? Well, it's May, so we'll talk about October. No, I'm busy Thursdays till November. So we're seeing a lot of intent and not a lot of action around relationships. And of course, there are differences across generations, but I'm hoping that with this pendulum swing, as we're feeling more and more disconnected, we're actually going to be more intentional about making relationships and connections a priority. Yeah. And I often find that, you know, even when I speak about this, you know, when I take

a look at new younger generations sort of saying like, okay, we need to put our phones away when we go out for dinner, we need to, you know, do those things. Nothing in in, I would argue, my generation really are taking those initiatives. Like we stay very lost in, you know, I think, right. And so like, you know, how, yeah, take it from the top, you tell me what is the biggest, heaviest thing in your heart in this space, because I want to know what is happening in this place of trying to not only develop relationships, but keep them. Yeah, I mean, you bring up a couple of important things there. One is that it is gen z or gen z that are being more responsible with technological use. We tend to blame younger

generations for having higher levels of technofurance, but what my observations are, are that basically young people, they're not responding to text right away. They have their phone on do not disturb. They will leave you on read. It is more kind of my age a little bit older than me who are putting everything out there on technology, who are glued to their phones. So I think this is a great opportunity for us to learn from younger generations. And when I work with groups, I'll often ask, do you keep your phone in your room? And I may have even done this at the event where we share space. I can't recall. Go do it. Yeah. But I asked you keep your phone in the room and I asked like, do you keep it in your room because it's your alarm clock? And then I asked, can you save up for an alarm clock?

And I know... Right. Yeah. Especially the type of clientele I'm working with, they can buy as many alarm clocks as they'd like. But I do notice that it's the younger folks who are being a little bit more intentional about technology and its interference in relationships and overall wellbeing and technofareance because perhaps because they grew up with these devices in hand, whereas for folks about my age or older,

like I'm on the older end of millennials, we didn't grow up with them. When I was 10 years old, I didn't have a cell phone. Cell phones kind of came into being when I was in high school, and even then students didn't really have them. That was kind of the early stages. So I'm seeing younger people be more intentional about technofareance and I think we can all

learn from that. Other kind of big things I'm seeing, folks are starting to talk about relationships more, which I think is really interesting and really meaningful because we're bringing that private or so-called domestic sphere into the public. And I actually think there's a lot of value in that because we know that when a topic or when a dynamic or when any organism is forced to exist in private, it creates more opportunity for shame, for abuse, for internalization, for assumptions. But the more we talk about our relationships, the more we say, for example, I love my partner,

I'm crazy about my partner, we have such a great time together, and we really struggle with ex dynamic. Maybe it's a parent-child dynamic among partners. Maybe we really struggle with a specific issue like finances. Maybe we really struggle with something that's quite important,

but we're uncomfortable with like finances. Maybe we really struggle with something that's quite important, but we're uncomfortable with like sexuality. The more I am saying that among friends, the more disarming it is. And all of a sudden everybody opens up. But also the more normalized that becomes that, hey, we're human, we're imperfect, we're living the best lives we can, and we're not having it all. Because one of the other challenges, of course, is with digital representations of everything, including hashtag couples goals. We're wondering why don't I have that?

And so my partner, Brandon, you met Brandon, you spent some time with Brandon, and he's on, or we've taken a break from our podcast for personal reasons this year, but he co-hosted the podcast for years. And the most popular episodes were those in which we shared our arguments and our fights, because people were like, what do you mean you fight?

What do you mean you argue? You seem so happy together. I'm thinking, man, living with me, every day could be a fight if you want to frame it that way, especially five days a month when I'm really on fire. Right. So you can love each other.

You can be kind. You can have all the tools. You're still human. You're still imperfect. And so I would love to see us move away from couples' goals to, I don't know, like perfectly imperfect or something like that. OK.

I really loved, I just want to circle back to this statement that you made because I think it's powerful. So isolation is sort of the breeding ground of shame and comparison and if I think a lot about you know when we're consuming information about what other people are doing the standards of practice how people are how much time how much they're having sex how much time we're consuming that now in the dark on our phones or in isolation. And you know, when we're at our waiting for our kids practice or we're doing various things, right? Before prior, one generation ago, even my generation, we did that in groups. We would go to the movies and talk

about it. We would gather around a TV even and talk about it. And now all of this, I think has added this level of that furthers the isolation because I'm not, we're not doing that. We don't look like this. And we forget so quickly that everybody's highlight reel is what we're getting. Right. And so how do you see that sort of like, I, I really liked that the it's, it's really, um, fostering those seeds of shame and guilt and comparison. And, and do you see then, I mean, we've seen a massive rise in divorce, a significant contribution to sort of delaying marriage or even forgoing a formal marital commitment. And, and what's your take on that? Is, you know,

are we feeding this constant comparison piece of like, we can never attribute, we can never rise to that, or is this whole idea of monogamy and long-term relationship fucked? Like is this antiquated in this very busy world that we live in? Ooh, big question. So as you said-

I know, I think about that all the time. I'm gonna get it all out, cause Jess knows. So you don't sleep, because we have to answer these existential questions. You can decide if I want to stay married. Just kidding, you're an Iwobi. Yeah, really big questions. So what I think is we need to focus on quality

over longevity. We need to focus on quality over mere existence. We need to be focused on quality over any sort of public representation or performance. And in a world in which we do sort of put everything on display, and I'm not saying that from a critical lens, listen, I love to take a picture of my food and post it. Like that is my greatest pleasure.

I'm eating this beautiful thing. I want you to see that I'm eating this beautiful thing. But in a world where we are sharing so much, so much becomes performative from the quality of our relationships or the longevity of our relationships to sex itself. Everything in that relational bucket becomes performative. So, you know, part of the antidote,

like the short answer is presence, right? Being in the moment, being mindful. Even if we start from dating, people will ask like, well, how do I know if they're a good fit? What should I be looking for on a first date? And I'll often say, look for nothing. Just feel what you're feeling. Ooh, listen, okay.

Let's highlight this. Look for nothing, just feel. And I think this is so critical because we all come in with our list. If I think about, Aaron is nothing that I ever dated before. He is like, I wanted somebody who was like funny and outgoing and like big dreamer.

Aaron's the fucking opposite. And most often I like dated people who like hockey players, they could lift a truck, but couldn't spell it. Like I didn't care. Like I just really wanted a big bicep. And my personal husband is like 6'2", and super slender. He's a ultra marathoner. Like, and he's the most conservative, quiet. Like we're in a room, I'm dancing on the table,

taking my shirt off. And he's like, can you sit? Mm-hmm. It's fascinating to me because the list that we make often forego our feeling, our true sense of, are we connected here on an emotional level? Can you tell me, yeah, so tell me more about that. I think that's brilliant.

I love what you're saying about your own experience because I think that's the most beautiful model for folks who are looking for connection, whether it's with a partner or with friends, or even in the workplace, we need to, as you said, let go of that checklist and just tune in to what we're feeling. And you end up with this beautiful partnership that you have of how many years because you weren't saying, nope, no way, like swipe next, swipe next. You're saying, okay, I'm feeling something here.

So even if you're on it from the very beginning of the relationship, I'm always like, check in with your top and your tail. How are you feeling? How do you feel in your body? How do you feel about yourself in the presence of this person? And actually as the relationship progresses,

whether it's a new friendship, a long-term friendship, somebody you're working with, a business partner, a life partner, those are good questions. That's a good question to check in with. How do I feel about myself in the presence of this person? And I think we can all relate to friendships, for example, where we hang out, we walk away, and we don't really feel good about ourselves, either because of the way we were treated, or we perceived things or how we act in this person's presence. And over time, those types of relationships don't tend to serve us well, right?

Those types of friendships either don't last or they're friendships that have more costs than benefits in our lives. And I'm not suggesting that friendship should be transactional, but we do have to measure what am I giving, what am I getting, how am I really feeling? And so from the dating stage to even the long-term marital phase, right? If you've been with someone 20 years and you're really fighting, or you're feeling a lot of tension, or you're feeling a lot of resentment build,

maybe you're even feeling contempt, oftentimes we'll focus on resolving issues instead of focusing on the feelings first. So I like to bring people back to how are you feeling? How do you want to feel? What can you do to feel more of that? And then once you've answered those first three questions, what can someone else, usually a partner or a friend

or whoever you're in this relationship with, what can they do? Because oftentimes we either start with the issue or we start with the external source of, well, if he would do this, if she would stop doing that, as opposed to here's what I'm feeling, here's what I wish I was feeling, here's how I can invite more of that feeling into my own life from my own experience or the singular dynamic. And then finally, and specifically what I'm asking from this person is, and we don't usually approach conflict or relational deficits that way. And so if we can just bring it back to that, it sounds a bit formulaic, but I find that

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Find your push, find your power. Peloton, visit Peloton at onepeloton.ca. Okay. I love that. And I think so much of this, you know, answer, I, I've thought this whole season about, you know, how do we become unlonely? And I think we're going to solve it the way we've always solved problems, which is, okay, here's the strategies. Do this, do this, do this.

Or cognitive behaviorally, I want you to do this, think that. And I think the answer to the whole world is truly in where you feel it. And I love when you say that because intuitively I have to get back to this place of what happens in this moment when, you know, for example, Aaron challenges me or, you know, makes, you know, I, I have a sense that it's like, you know, he's trying to, he's like, mm hmm. Yeah. Like, you know what that is?

Like, you don't even know what a spreadsheet is and like, you know, whatever. I mean, this is when I think about sort of developing our business, my business, my company versus it being ours and what that looks like. And one of the things that I just admire so much about you, Jess, is what you've built. You know, you speak internationally. You are often around the world doing such gorgeous things. I mean, at Marriage as a Business program has really been taking this concept of relationship and connection into who you spend the most time with really is a business relationship. It becomes a partnership that we've never, I mean, I never thought about it like that, particularly when I was younger.

Erin and I got married when we were 34 and we did a prenuptial agreement, which was asinine in small town Alberta. Like if you have to do that, then obviously you're on your way out. And I took it. I mean, it really didn't mean much in the moment, but it really said, I just said to him, you came into this with tons of experience and education and so do I. So let's come together and figure out how we're going to build this thing together because we want children and we want to give them way more than we have. We want them to be bigger,

better contributors to the world than we ever could be. So it really comes down to this idea of what does that look like? And so how does that fit with you? Because I wanna take it to intimate relationships and then I'm most interested, I think, in adult friendships, how that sort of applies. But talk to me a little bit about why considering marriage

as a partnership, particularly in this disconnected world, is becoming such a key to success. Yeah, absolutely. So the reason I frame my programming around marriage as a business isn't because I think marriage and business have everything in common, but because all of my clients, without exception, they all run our own businesses,

they invest so significantly in these businesses and they recognize that if I don't plan, if I don't assess, if I don't have advisors, and if I'm not willing to be flexible, I will fail. So they recognize that 100 percent, I don't need to cultivate the buy-in, they know this. So I'm asking them, if you value your relationship, whether, let's just say marital relationship, if you value your relationship, whether I mean, let's just say marital relationship,

if you value your romantic relationship, as much as you value your business, which every single one of them would profess they do, why are you so willing to formally invest to plan to have advisors to be flexible to review? Why are you willing to do that in business? But you think that marriage should just happen on its own. You think that your relationship should thrive without investment. I'm not suggesting that you have to spend 60 hours a week working on your relationship, but for you to spend none,

for you to wait until problems arise, for you to wait until things go awry, or worse yet, you are in crisis to invest, if you did that in business, you would not be where you are today. And so the reason I frame it that way is because they've already embraced this framework of investing in business.

And I say, well, do value it. They're like on it. Yeah, exactly. Yeah. And so it's not the exact same. Like you may need a very long business plan. Whereas for marriage, you know, I actually have some of them in some workshops,

fill out a plan. Now it's out a plan. Now, it's not a plan where you have to meet specific goals. It's a plan where we say, what do we want a year from now? We address different areas. So we address time. What does quality time mean to you? We spend a lot of time talking about time because with the clients that I have, their

number one complaint or their number one point of contention is around how they spend time. One partner works too much, one partner's on their phone too much, the other one's playing Candy Crush too much, one partner's too quote unquote obsessed with the kids. And so we have to talk about what quality time means because my definition of quality time may be very different than yours, may be very different than Aaron's, may be very different than Brandon's. So we actually just have to talk about it. And then once we've kind of figured out, okay, so quality time for me is conversation without phones

or quality time for Brandon is where I've carved out time and I'm traveling and I'm staying with him. And then we have to, as you said, exactly what you said, implement those strategies to make it him. And then we have to, as you said, exactly what you said, implement those strategies to make it work. And you know this, I think everybody in every field, from folks who are personal trainers looking at health, to doctors, to anyone in finance, to therapists,

everybody knows that people will understand in theory why they need to do things, but they won't necessarily follow through. And that, listen, I'm super guilty of that. I know that if I were to get more exercise, I'd probably feel better. But this morning I got up and decided to drink a coffee and scroll instead.

So I have the information and I'm not utilizing it. And I do feel that, you know, my job and very similar to your job is to provide the information and then provide them with frameworks and really simple strategies to implement. So for example, if they're complaining about time, they're fighting about time, and they're not spending enough quality time together, so we do this exercise together

where we go through all these questions related to quality time, which I'd be happy to send you to if you have a download section for the podcast. Oh my gosh, you put it in the show notes. Yes. I can send you that. So we do that together, but that's not enough because that's just the information. We also have to cultivate the motivation, which means like, why is this relevant? What's going to motivate us to do it? And then we need to enact the behavioral skill. So like information, motivation, behavioral skill. And so what I try and do is make it simple.

Like if I say, oh, you've got to carve out one weekend a month to go away together without the kids from most of my clients, that's not going to happen. Are there exceptions? Absolutely. But for the middle of the road, that's not going to happen. So what I say is you're going to take five minutes in the morning. It's five minutes to have coffee. And I listen, I don't come up with this stuff. I have so I'm so lucky I work with so many clients because it's not one-on-one. I'm working with

a different group every couple of days. But I have so many clients, again, they all run businesses, they're all busy, who say that they have 15 minutes in the morning that is just for them. They have their coffee, their kids can tear the house to pieces, their kids can be stuck in front of an iPad, they don't care. They start their day with 15 minutes. And I always find that if I ask people to do something once, 100%. Whereas if I say, can you do this for seven days or 17 days? It's a no. So we just start with once. And then we go up to twice a week. And then all of a sudden we never even have to work to three, four, five times a week. They're like, holy, I feel so much calmer.

I feel so much more validated. I feel like they're actually listening to me. I feel like at night, I'm not pissed off that they haven't asked me how I'm feeling. So I'm more inclined to be intimate. I'm more inclined toward pleasure and connection. So they need the information, obviously we need the motivation.

And then I like to make the behavioral skills super easy, right? Like 60 seconds a day or five minutes a week or one hour a month, as opposed to asking for more. And what I find is the less we ask, the more they do. I love that rule. The other thing that you said in there that I think is just brilliant is when we compare relationships that matter to business, I love the concept of advisors.

Now, as therapists, you and I both would say, I think everybody needs a therapist. I know that sometimes there's financial things that get in the way. Sometimes it's like, where do you find a good one and time and all those things. But really in this world, we don't have a script for particularly being a powerful woman

and navigating your own building of your business, following your dreams, you can be anything you want. Also, you need to coach hockey and be at the PTA meetings or whatever. I don't even say call it PTA anymore. But like, it's like, there's no script for this. So when we look to our mamas for advice, advice, right? Many times, you know, I've gotten and I've, you know, I have the best, I had the best mother-in-law and I think I would argue one of the best moms in the world. And they're operating from a script where they are all they know to be true, right? Like, are you gonna be home to put them in,

like what happens when you're traveling so much? Like all of those things. So I want you to really think about this concept of advisors because it's like, who in your world right now do you admire? And who do you feel seen with and by? Because particularly in this world of success, whatever that looks like for you. And I would argue Marty and I probably talk about this a lot is who are we sitting with that can advise us in this space?

Because you will outgrow people just because you've been friends forever. I mean, that's often how we define if we want to move into this now adult friendship conversation, you know, because I think that, you know, your business partner or your partnership in marriage is often, you know, so critical to consider, but I will spend more time with my friends than I do my partner. And as my kids get older, I spend less and less time with them. Right. And so the idea is choosing wisely in those relationships that are going to spend the most amount of time with you and that you have some leverage, some capacity right now to think about who does get to be in your intimate space, who does get to fill your soul, because what does

that do? Right? So talk to me a little bit about, you know, building those relationships on by feel and why adult friendships are so fucking hard. I'm fascinated by this topic because I think it's the antithesis to loneliness. I think it's the antithesis and we suck at adult friendships, I think, but tell me more. I agree. Listen, I'll speak personally. Like I feel a lot personally, not as a professional, as you're saying all of that, because as somebody

who works for themselves, who has built a business, it can be hard to connect with people who have a slightly different lifestyle. I imagine you report cord podcasts early in the morning or late at night. You go to events on the weekend that you have to speak at, and so you miss important gatherings of friends, right? Like I think I've lived this my entire life because I started a long, long time ago as a bartender. I was bartending to make money and go through school. And so I really couldn't go to birthday parties on a Saturday night.

That would be like my asking a friend to come on a Monday morning because Monday mornings are off for me. Do you know what I mean? But there was always a struggle there. Then you become an entrepreneur and I work as I said almost exclusively either with entrepreneurs or folks who run companies and the way we work is quite different. Our hours, our expectations from clients, from boards, from whomever we are responsible to are different. And you probably ran into it when you have kids, right? When you have kids, your lifestyle becomes very different than those of friends who don't have kids.

So I think that sometimes it's just lifestyle that gets in the way. I think that we may have more in common values-wise with one person, but if our lifestyles don't align, we simply can't make it work. With a partner, it's slightly different because you tend to live in the same space. So even if you're on different schedules, you're gonna pass each other

and probably carve out time for them. And I guess that's really where the lesson begins. If you can carve out time for a partner, you can also plan ahead with a friend. Yeah, And see... I'm giving advice I don't follow. I'm very bad at planning ahead with friends, but I think we can also be flexible, right? So if something's last minute, I'll just share. Okay. So I'm very last minute because I come back to Toronto for usually two, maybe three

days at a time. I have family responsibilities here with my father, and then I have the priority of my mother and my father. And so they do come first that it just is the fact when I come back to Toronto. And so I won't tend to book anything, but my friends are accustomed to me sending a text at 3pm saying, do you want to come to the wine cellar at 7 p.m.? And so people who are in my inner circle

know that I just really want to see them. And it's not that I wanted to leave them for last minute, but this is kind of what I had the energy to do with the time change with sometimes the drain of my father and all of those things. But people who I maybe don't know as well might think Jess doesn't care to see me if she's inviting me four hours in advance. And so we actually have to talk about that. And that's probably advice I should take as well.

Maybe I don't communicate as well to people, to friends. And I'll tell you the truth. And I think that I'm probably the perfect bad example. I probably just don't invest in my friendships as formally as I invest in other relationships, like my relationship with Brandon and my relationship with my parents. I have to say, I love what you said about who do you really admire? Who can be your formal or informal advisors? And I think that's a great point for everyone to reflect on right now to answer.

Who do you admire in relationships? Not necessarily business, not necessarily as parents, but literally whose relationship is a great model for you? And I can answer that right away. It's my cousins, Mike and Denise. And I, well, they're not both my cousins. Mike is my cousin. He's married to Denise. And I love being in their presence because of the way they speak to one another, because of the way they laugh with one another, because of the way they laugh with one another, because of the way they support one another. And I may not go to them and say, hey, there's this relationship issue I'm curious about,

can you tell me what your perspective is? But the mere act of spending time with them and prioritizing spending time with them, because they live in Jamaica, and so we have to get together in different places, the mere act of being together for me is life-changing and is a huge source of support, not just to me as an individual, but to Brandon and I as a partnership.

Okay. So let's unpack that because I think what you said earlier was really like, oftentimes our friendships happen out of, you know, just sort of who we're surrounded with. So who's on the hockey team or who we've known the longest and who, and I really want to caution, you know, I think sometimes it's, it's about making a real conscious decision about where you're going to spend your time because when it becomes easier, which, which is often, it's of convenience.

Okay. So I'm at the hockey rink most of the time with these people or we've known this one the longest. And, and sometimes that's where you find and cultivate the best friendships. That's where things sort of happen. But I, I'm so fascinated in this idea of misery loves miserable company, because when we are spending time with people who just sort of like, also, yes, like I, my marriage is in shambles and I fucking hate this guy. And I think this is terrible. And you know, let's talk about everybody in the community that that doesn't fill my soul to the degree that it used to.

And when I think about why that is and where I want to be and who I want to be for, you know, my relationships and business, um, it, it's really struck me in this last year. And I don't know, I don't know if this comes with development, but really this idea of consciously taking stock of who I feel the best with when I'm at that table, when I'm eating dinner together with them, when I, you know. So choosing those things. And then what does it look like to step away

from previous relationships, right? Would you just stay with somebody because well this is the expectation and you know we we know each other intimately from grade five, right? Two of my best friends we met in kindergarten and when I step into the presence of Tanis and Leah, Tanis feels like home to me. Uh the smell of her hair, I often tell her this and she freaks her right the fuck out, but I feel like anytime anything bad happens in my world, when anything bad happens, you know, when I know when my parents die, I will need her. And she is not articulate. She doesn't ever know what the fuck to say. She grew up with me, right? I would fill all the quiet spaces, but it is her physical presence that changes everything. The day Leah's dad died, we just sat there.

And I want, I mean, I'm so interested in this concept of loneliness as being really, you know, because you, I love this concept. We put together this question, but we often assume that being in a relationship offers protection against loneliness, but this isn't always the case. So what does it mean if you have a partner, a best friend, a group of friends, but still

feel lonely? And what can you do about it? Because doesn't this add to that place? Just because we have, I mean, again, I will ask you the question in a second, but I think about being in my 20s, it was all about numbers. Being in my 30s, it was all about who's who and I like, can I, can I fit myself into this place because I really want to be liked. And I watched my daughter at 11 trying to navigate that too. Like who's the, you know, and now

in my late 40s, it's like so much more about a feeling and I can be in a room full of a thousand people. I can go into the hockey rink and still, I feel so fucking lonely because sometimes there's, I feel like a fish out of water. And then sometimes I'm just, does that make sense to you? Oh, of course. I mean, personally and theoretically, right? We think about that feeling alone can be more about the quality of social interactions.

Again, back to your point, right? That quality. Like in a crowd, you can feel lonely if you feel that connections are maybe shallow or unfulfilling or just not a fit for you. Like, so I'm mixed race. And I kind of... Yes, you have a gorgeous Chinese,

Jamaican, Irish, Canadian. Um, you got to see this woman. Like, honestly, it is the most beautiful combination of things. Okay, so tell me. Yeah, I think I've straddled a lot of fences throughout my life. And so one thing, you're really kind of reminding me that for a lot of us, and especially for women, man, it takes us a long time to figure out, even though we're so sharp, we're also raised to be people pleasers.

And we're raised to be everything, as you said, whereby we do too much, we spend too much time with people, we're asked to go someplace and we don't really even think about if we want to go. We think about if we can make it happen, because we're such performers on top of everything. And so I think for most of us, it takes being worn down and worn out and probably burnt out before we stop and ask the really important questions you're asking, is this relationship feeding or soothing my soul, right? And so we can absolutely feel social isolation,

even in the presence of others, if we're not really getting the quality of connection that we're looking for. But I mean, I know I wait too long, but to go back to what I was saying, sorry, I do go off on a tangent. I know when I'm with my people. And as somebody who's straddled many fences, culturally, racially, in many different realms

of my life, it's only now that I've really figured out in the last five years, like these are my people. I'm not always going to be with my people. Sometimes you're gonna be in the hockey arena and those relationships are highly valuable as well. And beautiful humans, yes indeed. Absolutely and every relationship matters, right? You've seen the research that the way you interact with the barista in the morning affects your quality of life. The way you interact with... Say it again. Yeah, every single person. And I know that I talk to everyone.

I talk to everyone. It's so funny because my mother's Jamaican. You do. She used to talk to everyone and it used to drive me bananas as a kid because I think I was trying to be Canadian, is the truth. And now I know that I am more comfortable saying hello to people. I'm more comfortable interacting with strangers. And people will say that I am more comfortable saying hello to people. I'm more comfortable interacting with strangers and people will say, oh, those are shallow connections. To

me, those aren't. Like if there's human warmth, if there's a feeling of community, there's real value there. I don't need to know everything you're feeling. I don't need to know your whole life story. There's still love between us. We're in this human race. Yeah, we're in this human race. This big community. But it's taken me a long time to figure out who my people are. And that's the language that I personally use. And that's a language that a lot of, I think,

my friends and my community use around, like, are these my people? I don't always have to be with my people. But when I am carving out intentional time on a Friday night, when I'm taking a Thursday afternoon off work, when I have three nights in town, I am picking my people. Yeah.

And you say intentional, or you use some language around that, that relationships should be intentional, not just proximal. Like, yes, there's connections everywhere you go, but as we get older and we have less time, right? Like you are, we're usually sandwich generation. You're caring for kids, you're caring for parents.

You have lots of responsibilities. You run a company. You also have a marital partnership. With all of that, you don't have a ton of time to allocate. And nobody wants to be like leftover time. Amen. Amen. So Mike, you know, the question to me is, you know, again, cutting them loose, like

finding them, keeping them. You know, we've talked a lot about those kind of things. But I think that there's also a necessity where we don't have a massive script for for, you know, we tend to just as we see kids these days do, you know, the ghosting. I'm it's easier to just not have a conversation. I'm going to just step away and step into a different how. What is it like to first of all cut friendships loose and then what does it look like when... How do you know when it's time to end an intimate relationship?

Well, I think it can be harder to end a friendship versus an intimate relationship because especially if you're in a monogamous relationship or any sort of intimate relationship, you know you're in a monogamous relationship or any sort of intimate relationship, you know you're in the relationship. Whereas with friends, you can kind of drift apart, you can come back together, you can not have time for one another. So there are many ways we communicate that a friendship or a connection isn't a value to us.

And oftentimes we leave ourselves and leave them wondering. So I just wanna take a quick step back and kind of address when when do we know? Right? When do we know that it's time to call it quits or take a pause? And I think we have to differentiate between needs not being met in the relationship

versus needs not being met more generally in life. And I see this more often in intimate relationships than in friendships because we tend to expect an intimate partner to meet all of our leaves needs. So somebody will say, like, I just don't have any excitement. And I and then I'll ask them, well, where do you get your excitement in life? Like, what do you do to create excitement? And they don't really have an answer there. So oftentimes we'll attribute emotional issues to our primary relationship. I think it's it's an association of proximity

and saturation and familiarity, right? We blame what's nearby, we blame what's familiar, but sometimes we over attribute both benefits and deficits to romantic partnerships. With friends, it can be a little bit more difficult, but I think we go back to how do I feel about myself? Not how do I feel in the relationship, but how do I feel about myself with Not how do I feel in the relationship, but how do I feel about myself with this person?

Do I like myself? Am I comporting myself in a way that I'm proud of? If you find that you don't really like yourself or you don't like how you're feeling about life after spending time with somebody, or if you're dreading getting together, it may be a sign, not that you have to say, hey, this friendship is over,

but you're going to prioritize that friendship a little bit less. If on the other hand, you know, a friendship is draining you, is toxic to you, maybe you feel burnt out by a friendship. That's when you may have to have that conversation to say, I really care about you.

I do want the best for you. And for me right now, this is what I need to do, whether it's I need a month where we don't talk about this specific issue, right? Because we do know that sometimes, you know, friends can unload and treat you like a therapist, especially if you are a therapist. But or you may need to say like, you know what, this, and I see this all the time, I'll actually say that young people are quite good about this, they will talk and say, you know what, and I see this all the time. I'll actually say that young people are quite good about this. They will talk and say, you know what, this relationship isn't serving us at this time. And I think young people are quite good about creating less of a hierarchy of relationships,

whereby the intimate relationship doesn't always have to take precedence. And they treat their friendships intentionally, as you're suggesting, and with love and care, and with the same respect, they treat their friendships intentionally as you're suggesting and with love and care and with the same respect, they treat their intimate partnerships. So when do you know when you no longer feel good about yourself? Now, that doesn't mean if you're in a marriage and you're not feeling good about yourself

that you have to call it quits, but I'll often suggest a number of questions, which is, what are you feeling? It kind of goes back to like, what are you feeling? What do you want to be feeling or how are you feeling? How do you want to be feeling? We talked about that. And then also why I think why is very important.

Why do I care about this person and why do I invest in want to invest in the relationship? I actually always start with why, because sometimes people will come to you saying they want to repair something. But if their only why is for the kids. If their only why- Yeah, I was gonna say that, but that's your number one.

If their only why is the stigma of splitting up. If their only why is, well, we've been together 25 years and we've built this life together. Ooh, you still have lots of years left in your life. And if you've let it come to that point because you know this better than I do, oftentimes people do not go to try and repair their relationship or get the support they need

till seven or many more years after the very serious damage has been done. And if you have been treating each other like garbage for a decade, if you've been treating each other with contempt, if you have been finding no joy in this partnership for a very long time, I'm not saying it can't be repaired. I do believe many relationships, most maybe relationships can be repaired. But if you've done all this damage and you still can't come up with the why of, I admire this person. And the bottom line is I really like this person. I don't worry about love as much. I think it's almost easier to love and care. Hopefully we all love each other,

really. But do I really, really like this person? When I think about my relationship with Brandon, I'm like, I like this man. I don't wanna say better than everyone, but that is really how I feel. Like I just like everything about this person. I want this person to have the best life ever. I could name you 100 whys. Sometimes I can't get people to one why.

So if we can start with the why and you can't answer it, that doesn't mean like a one-shot deal. Okay. You can have this conversation tomorrow. You can have this reflection in a week, in a month. But if you can't come up with a why you value this relationship, why you want to repair it, it might be that you don't want to repair it. And if you don't have the intent and it's not a mutual intent, it may in fact not be repable. Okay, got it. So it's that sense. And I know that Gottman's talk about when the feelings of contempt come in,

when I think about people when I do couples therapy, it's like if there is a deep disdain there, it becomes very difficult. Now the question is why? Why do we have that feeling? Where did it come from? And that's where the work is, right? Because it's easy for, generally speaking,

every couple that comes in that are struggling say to me, it's here, it's him, it's him, it's him, it's, you know, whatever. But it's just like, they don't listen, they don't get it. Or like, I don't know, I just feel whole. Like, you know, whatever that is. It's sort of, I think, being able to unpack some of that is critically important.

And the end is not nearly as important as I think unpacking it. But man, that's hard to do. Isn't it? Yeah, you know, we think that we have this opportunity to like speak for an hour, but it's really just it's a drop in the bucket, right? Like there's every situation is so different. The layers are always so different. It is what's's the name of that? Viennese Austrian cake, the sesh, I don't know, that's many, many layers. That's what the relationship is.

And you can cook one perfectly, or you can repair one, or you can put one on, but there's always something else. One thing I do tell people is that change doesn't have to be dramatic, right? Like if you've gotten to the point where you no longer express affection or care, you literally just have to do it one time to get started, right? It's not like if you

clog your arteries and you have to go have surgery to have it unclogged or whatever it is you need to do. Like if you, if you clog your arteries, you can't just have a salad and it's better. Whereas if you have, I guess a rift that needs to be repaired, for example, you no longer express affection or care, you actually just have to do it once and then a second time and then a third time. And I do see couples oftentimes just need that reminder that it actually doesn't have to be that complicated. You may have had an issue that's persisted for 10 years and you actually can decide to let it go.

I've seen that, but it has to be intentional, right? It's not something that's just gonna happen. You have to say, you know what, this is bothering me. Here's some of the reasons from my background why I'm particularly triggered by this. Here's some sociocultural reasons why this might be really hard for me. And then here's the relational or dynamic reason,

and we can address that together. But part of the others, you know, my stuff and the sociocultural stuff, I might be able to let that go. I mean, I've been in that boat where you're upset at someone and you're kind of holding onto it. And every time you think about it,

you hurt or you struggle or you suffer. And then you're able to sometimes, not with all issues, okay? Not with big, deep sociocultural issues that are tied to identity, but with individual issues, I might be able to say, you know what? I just have to let this go and I'm going to. And people do do that. Like we can say there's layers, but also we can make decisions and make it uncomplicated. Right. And I think oftentimes, you know, I've said this many times, my biggest focus in couples

therapy is to get two people to look at each other. And it is really quite that simple, because they often, the hardest thing we will ever do is look into the eyes of the people we love. And really having somebody facilitate that gives us enough data to suggest that if, when I do that, if I don't feel it anymore, and it's such a cliche, but feeling it becomes really important. And if you can honestly get into that, you know, place where we slow things down, either

because somebody's facilitating that or we get brave enough to do that in our relationships, I think then, particularly as women, then being honest about that, there isn't anything here anymore. I've grown, you've changed, whatever that is, this is not who I thought, you know, this was going to be. Then we have some data to suggest, okay, now what do we do about this? But I, you know, as you're talking about this, I think some of the hardest things to do, particularly with our intimate relationships, is have those conversations. And I think that that is the difference between intimate

relationships and friendships, is that I don't think it's always necessary to do that in friendships. Because I think sometimes, you know, the ones that are deepest and matter the most, please, please do that. Right? We, we, I think that's the best. But you know, when we think, think about peripheral relationships, people come in and out of our lives. Um, you know, really noticing how you feel about those things and taking responsibility for like, this is who I need here. Not they're going to have to meet some criteria or they talk about stupid shit or they don't understand what it's like to be this, you know, and you know, just to your point about being a, you know, successful entrepreneur, you know, we, we show lots of things online about, you know, this is what it is and I'm flying here, we're

doing these things. The fucking behind the scenes things that is really, really difficult, right, which is, you know, 89% of the days, the people who tend to get it the most are the people I need to be around. Because I don't want to have to explain that all the time. This is really how hard it is. If you don't know that to be true about this journey, then those are the ones that we really need to hold close and really wondering, you know, when you see that in other people's highlights reels, knowing that that is not the fucking truth and that we do need people in those quiet dark moments and that, that taking away that layer of sort of invisibility that is there and just knowing that to be true that we are all, many of us particularly as women are so lonely these days, really stepping into those relationships and knowing that whatever you have to give

can really foster a deep vulnerable connection is what we need. You don't need to do it all the time, but really pick where you play and go all in. Think so? Oh my God. Okay. I think we're hard on ourselves too.

Right? We think our relationship is never good enough. Our friendships are never good enough. There's, you know, another reason we feel lonely is social comparison, right? Right? We think our relationship is never good enough. Our friendships are never good enough. Another reason we feel lonely is social comparison. Right? So you talked about being lonely in a crowd, but in a crowd or among friends, sometimes we perceive ourselves as lonely because we perceive others as more connected or more engaged. We do this in romantic relationships. Oh, God, the story in our head. Yeah. Yeah. And I the story in our head. Yeah, yeah.

And I mean- It's ridiculous. Definitely with friends, it can even be, I think, tougher because the way friendships are represented, for example, in pop culture is so idealized. Like now we're seeing kind of more messy relationships, messy marriages, but friendships still, we wonder, well, why don't I have six friends from college

that I talk to every single day, right? Or why don't I have that friend who's over at my house every day with fresh baked bread? And so we need to go, where's my bread? Eileen, I have a friend, I have a friend, Eileen, who bakes, where's my bread? No one's baking bread these days. Eileen, where are you? Yes, exactly. Oh my gosh. I, you know, I love so much of this, Jess,

and I'd love to have you back because what I think is so interesting, your most recent book is called The Ultimate Guide to Seduction and Foreplay. And I think oftentimes, when we first met, we talked a lot about how people get really, I think, interested in the intimacy of sex and what is an orgasm and how do you do foreplay and what does that look like? I think interested in the intimacy of sex and you know,

what is an orgasm and you know, how do you do foreplay and what does that look like? And I loved, you know, listening to you speak over the years about, you know, just how brilliant you are in that space. I'm glad we used our time together to really talk about, I think all the things that come before that, which is really what is it, why is it so difficult to be connected and intimate and truthful in this lonely world?

And so I thank you so much for being just so brilliant in this space. You are such a hero to me in the business you're building, in the decisions you've made, in your relationship and you know, just how you care so deeply for your family. So thank you for being here today. I know our community, I hope, fall in love with Tinder Canada's dating and relationship expert. Because we didn't even get to talk about the online space, which you're so brilliant in. But there's so much more. Where can people find you? You can find me at happiercouples.com. And thank you so much.

Thank you for making this space. You always like you shine a spotlight on me, but on other people. And that's so appreciated. And I think what you said really hits the nail on the head that the sex part is actually easy. Mechanics are easy. It's everything that comes before it. And if we don't lay the foundation, we can't even begin to talk about orgasms. So we can do that another time. Oh, yes, please.

Did you see how I strategically fucking got around that one? So I guess I need to do a little more therapy. And then Marty was excited about the orgasm talk. Look at her, she's sad that we didn't get there, but next time. Okay. We'll talk about eight types of orgasms, Marty, eight types of orgasms next time. Oh my God. Could you just give me the eight real quick? What? Oh, Marty would like to actually do a guest appearance. Holy shit. So, uh, I mean, we have like 30 more seconds. Tell me the eight kinds, cause I feel like this is going to keep everybody to the very

end. First of all, um, there are more than eight. I just, you know, picked eight, but we tend to talk about like for women, clitoral orgasms versus G-spot orgasms versus blended orgasms versus multiple orgasms. Of course there's penile orgasms, there are prostate orgasms. Some people say there are cervical orgasms. Some people say there are cervical orgasms. Some people have nipple orgasms. Should I stop there?

There's more. I'm gonna tease for the next time because I have many on the tip of my tongue. Wow. I am fascinated. Marty, this is your jammy. She's in. She's in.

Marty's like the next part two. Yeah, you and I, Marty and I are gonna do the next one together because she'll be able to carry this conversation. I'm going to be in the corner like, oh my God. Okay. My mom's listening. It's going to be fantastic. Okay. Dr. Jess O'Reilly, you're the best ever. Give all my love to Brandon and I can't wait to connect when we're in Toronto again, because I just know you're just getting started. So thank you. Thank you everybody for joining us today. Stay tuned for part two, because I know that's probably going to get the most listens on

the planet. In the meantime, take care of yourself, take care of each other in this lonely world. And I'm just so grateful that you spent your precious time with us today and I will see you here next time. Unlonely podcast is produced by three incredible humans, Brian Siever, Taylor McGilvery, and Jeremy Saunders, all of Snack Lab Productions. Our executive producer, my favorite human on this planet is Marty Piller. Soundtracks were created by Donovan Morgan, Unlonely Branded Artwork created by Elliot Cuss, our big PR shooters are Des Venot and Barry Cohen. Our digital marketing manager is the amazing Shana Haddon. Our 007 secret agent from the talent bureau is Jeff Lowness. And emotional support is provided by Asher Grant, Evan Grant, and Olivia Grant.

Go Liv. I am a registered clinical psychologist in Alberta, Canada. The content created and produced in this show is not intended as specific therapeutic advice. The intention of this podcast is to provide information, resources, education, and the one thing I think we all need the most, a safe place to land in this lonely world. We're all so glad you're here. Hey, beautiful souls. I've got to share something that's been a total game changer for me. Joe Fresh has just unveiled their new active wear collection.

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