A Bit of Optimism - The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan

Episode Date: September 15, 2026

The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle. It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now. Her argument: we need to correct the lessons we’ve learned when it comes to dating. The person who’s great on a first date isn’t necessarily great at a relationship. Instant chemistry isn’t always a good sign. A red flag could just be an imperfection. And keeping our options open has made a lot of us genuinely bad at choosing someone. Amy is the founder of Renew Breakup Bootcamp and the author of Unsingle: How to Date Smarter and Create Love That Lasts. For nearly two decades she’s looked at dating through psychology and neuroscience — why we’re drawn to certain people, why relationships fall apart, and what actually predicts whether one lasts. She started her career helping people end relationships… Now, she teaches them how to build one. In this episode you'll learn: ➡️ Why “instant chemistry” is one of the worst predictors of a lasting relationship ➡️ The quiet qualities research says actually predict a happy partnership ➡️ Why dating skills and relationship skills are two completely different skill sets ➡️ How the algorithm rewards red-flag advice 10X over green-flag advice (and what that’s doing to you) ➡️ Situationships: why the breakup hurts more when there was never a breakup ➡️ “Leaky energy,” micro-cheating, and the honest test for both ➡️ The 9-date experiment Amy gives clients who are stuck dating the same person ➡️ How the right relationship shrinks old wounds  ➡️ Why discomfort is a critical skill dating requires Amy’s advice isn’t about finding a better person. It’s about becoming someone better at love. And that’s advice all of us could use!  This… is A Bit of Optimism. + + + This episode is brought to you by SAP. Bring it with SAP GROW. The AI Cloud ERP for any size business. Learn more at https://SAP.com/GROW + + + To get a copy of Amy's book, Unsingle: How to Date Smarter and Create Love That Lasts, head to: https://missamychan.com/#books  + + + Chapters Chapters 00:00:00 Why Modern Dating Advice Is Making Us Worse at Love 00:02:26 From Broken Heart to Breakup Bootcamp 00:09:50 Why Dating Feels Harder Than Ever 00:11:35 The Two Different Skill Sets: Dating vs. Relationship 00:12:26 Online Dating and the Imagination Problem 00:14:17 The Coffee Date Defense and the "Five Out of Ten Rule" 00:15:53 The Cure for Avoidant Attachment 00:18:13 The ADHD Love Bomb Confession 00:24:49 What Self-Care Culture Gets Wrong About Commitment 00:30:31 Situationships: The Safe Space That Keeps You Stuck 00:33:07 Leaky Energy and Micro-Cheating 00:35:08 Amy's Seven-Year Relationship and Emotionally Corrective Experiences 00:39:28 The Instant Chemistry Trap 00:40:59 The Nine-Person Dating Experiment 00:44:37 Why Young People Aren't Dating Anymore 00:45:49 Bad Feelings Don't Mean It's Bad 00:48:02 The Single Skill That Saves Relationships + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Leaderful: https://simonsinek.com/leaderful Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek

When I look at my favorite couples, and I have a few of them, like the couples that I like, I want a relationship exactly like theirs. Like, my God. Yeah. If I ask any of them, what's your secret? They all say the same thing, which is we do the work, you know? I think what you've explained when you talk about the friends that you have that have great relationships and the ups and downs and the working through it, you describe a great relationship.

And I think a challenge that people have today is this mindset that they need to meet the perfect person first and then it'll be great. We need to meet people who are good enough and then we jump in with two feet and then through going through the stuff. It's the hard stuff when you're there for each other that it goes from good to great. Some of the dating advice that we follow might actually be making us worse a dating. Know your type. Trust the spark. Watch for red flags. Never settle. Protect your piece, and if someone isn't quite right, there are hundreds of other options waiting on an app. The problem is, the person who's great on a first date isn't necessarily great at a relationship. Instant chemistry isn't a good sign. A red flag might just be an imperfection, and keeping

our options open can make us pretty terrible at actually choosing someone. That's why I wanted to talk to Amy Chan. For nearly two decades, she looks at dating through a sort of psychology and neuroscience lens. Why we're attracted to certain people and why relationships fall apart. She's also the founder of Renew Breakup Boot Camp and the author of Unsingle. Her work makes the case that finding love isn't just about finding the right person. It's about getting better the skills love requires. It turns out dating takes practice. And so does staying in love. If you like what you hear, please remember to subscribe. This is a bit of optimism.

This episode is proudly brought to you by SAP. Building trusting relationships with clients, it turns out, takes more than simply being an expert in your client's business. It actually is about empathy and being willing to step outside your own comfort zone. To learn more about SAP, the AI Cloud ERP for businesses of all size, head to SAP.com slash grow. I'm always fascinated about people's careers and how we stumble into them. and I think you and I are very similar

that this was not our chosen path. I never imagine I'd be doing what I'm doing. I don't think you imagine that you'd be an old relationship expert. You didn't come from this world. You didn't study it. And for so many of us who stumble into these things, it's our personal experiences that sort of,

you know, the solutions we find and the struggles that we're finding. And so you started not by talking about how to people, you started by not trying to help people have relationships, but how to end them, right? Tell me about what happened to you. Yeah. That unleashed or opened up an entirely new career, your accidental career.

Yeah. So I was in a relationship in Vancouver and I thought I was living the dream. And back then living the dream meant you date to get married and then you have children. And then the plan I had with this guy who ran a business was I would write on the side for fun. And we would have kids and everything was set. And then a series of things happened. I lost my job. I moved in with him.

And then he cheated on me with a former coworker of mine. And it wasn't just a relationship that fell apart. So much of my identity and future was wrapped up in that relationship. Like I am the girlfriend. I'm the wife. I'm the mother. I was, yeah, the perfect girlfriend training to be the perfect CEO's wife. Like that's what I thought was my dream.

And that shattered. And I shattered. It was dark. Like it was so hard. And as an achiever, like, there was nothing I could do to get out of that pain. How long were you guys together? Two years. Okay.

Yeah. So I just, I really struggled. And when I came out of that, which took quite a long time, like two and a half years, I was like, what happens to those people who don't have friends that will lend them a couch or know what books to read or have a therapist? So I was like, I have to create what didn't exist for me. So that's what I did. And what were the things that you found for you that helped you get out of this malaise for,

I mean, two and a half years to be stuck in mourning is a long time for any kind of loss. For sure. Relationship or otherwise. Yeah. And look, the intensity of the pain, I think, lasted six months. That's when it's like constant rumination, revenge plotting. But, you know, after that, like... You didn't do anything, did you?

I didn't, but I had to really good plans. I want to know one. I want to know one of them. Buying bedbugs off the black market and infiltrating her home and his home. Wow. Wild, right? It was bad. But looking back now, you can recognize that if you did that, you're the crazy one, right?

Yeah. Thank God I didn't do it. Oh, my God. Okay, this, I'm fully aware that, you know, this episode, we're going to be giving advice. This is not the advice part. Don't do it. Don't do it. We will not be giving instructions on how to get on the dark web or any links for bedbugs. Yeah. So, I mean, like, and after a period of time, like that intense pain went away, but I was resentful.

And, like, I was trying to date, but I had to close hard. And any person I could rally into my corner about what a victim I was and what a villain he was, that would be the story. And it really wasn't until like two and a half years later I'm having coffee with a friend, catching him up. And I'm like telling him the story, I'm like, what this guy did to me. And he just stopped me. And he's like, so, Amy, does his story serve you? And I'm like, no. And he's like, oh, can you, was there any time when he did love you and he was kind?

And I just thought about it. like, yeah, there was this and that. And I just realized in that moment for the last two and a half years, like, all I could see was it dark because that's all I was looking for. And I went home that day and I wrote him a letter of forgiveness of how I grew. And it was like all those things I was doing that was like, this isn't helping. It's like it all came together like glue and it just hit. And I just didn't have any resentment for him after that. What was the impetus? for you to, so you found tools that helped you that started with your friend sort of telling you that it doesn't serve you this story. And then set you on a journey of healing and moving forwards and looking out the front mirror, out the front window.

You know, were you starting to dispense sort of armchair advice to your friends that was working? Did your story help others? Like how did you go from healing yourself to giving away what you had learned? Yeah, I looked at everything that I tried and what worked and what didn't. And from there, I was like, okay, these things really worked. I was a writer. I've been writing about relationships for 20 years. So I would write about it in blogs, in different columns.

And then when I had this idea, I brought the best experts in that specific thing. So if it was cognitive behavioral therapy, I found an expert in that. somatic therapy, and I just learned from them, and I created the curriculum. Yeah, and that's how I started. It started with like seven people. Half of them were my friends. I love that. I mean, that was my story, too.

Yeah, no, I started giving talks in people's living rooms with their friends. Yeah. Yeah, that's the same, same, same. I found you on the Internet. I saw you on Instagram. Okay. And I was like, so this is the best thing about having a podcast, right? Which is if I see somebody on Instagram who I think is really, really cool,

and I was like, hmm, I could, this would help me, you know. I get to invite them on the podcast, I have a conversation. Yeah, it's about you, but it really is about me. We were talking before we turned on the cameras about my relationships, and I probably fit many of the patterns. I do think that there is a lot of judgment we put on ourselves, society puts on us, an expectation. For example, there's a lot of pressure that,

whether it comes from our families, ourselves, society, whatever it is, you know, to get married, have the kids, white picket fence. I mean, the fantasy you had, I'm writing a lot about friendship these days because I think that our society's over-emphasized the romantic relationship and under-emphasized the friendship, the platonic relationship. And I have romantic friendships. Now, that doesn't mean that they're sexual, they're not, but they're deeply intimate. Yep.

And there's love and there's care. neither of us want to date each other but they're very fulfilling and it's kind of like you looking for the darkness which is if I ignore all the goodness that I have in my friendships I will feel lonely that I'm that I'm not in a relationship

but if I appreciate the friendships it takes the pressure off which probably makes me more datable anyway you know if there's just a lack of you gotta get into this do you think that dating seems to be more difficult these days I know young people are later to have sex.

Young people are, the tenure of relationship seems to be shorter. What is the reason? You've met a lot of people of all ages. Yeah. Can you discern that it's a young person challenge or is it a current day challenge? Like, why does dating feel more difficult than it used to? And it's too easy to simply say the internet. Right.

Yeah. I think dating apps have changed the way that we, meet people, but they change the way we think about people. And if you think about the act of just swiping a hundred times a day, that's what I used to do. Just swipe, swipe, swipe, and the 100th person I would look at. Like, it's just, there's so much incoming. It's shopping. And we know through research that the things that you're being so picky on for a dating app, height, looks, hair, whatever it is, if you met that person at a dinner party, you wouldn't have that same judgment. But we're meeting people in these ways and it's changing the way that we see people. So we can even go on a date,

have a good date. The second date, we noticed they wore flip-flops. And suddenly, if you remember all the stuff you're being fed on Instagram, what an ick. Or maybe they asked you for coffee and not a dinner. And that advice is being told to you that a coffee, what a waste of your time. So I think that we are walking around with barriers around our heart. We don't trust the media. We don't trust your government. We don't trust the neighbor. We don't trust anyone. And so how can we connect and see another person as a human being with flaws and have empathy when they mess up when we are doing that? And can that be done with internet dating? I think it can be done, but I think that there are a certain set of skills we need to learn for dating. And there are a separate set of

skills you need to learn to sustain a relationship. And there are people who are great at They're charismatic. They know what to say. They're adventurous. But those people aren't necessarily good at being a partner. I, in my experience, what I found fascinating about online dating, and I've done it, and I've had success with it. I've also made a lot of friends.

But what I found really interesting is pre, you know, if you meet somebody offline, whether it's at a dinner party or a museum or wherever it is, the initial, connection, there's charm and there's chemistry and the sense of humor. And it's after you make the connection, you say to the person, can I have your number? And then you go on the first date. But there's already a connection before the first date. In online dating, the only thing you have is a picture, maybe some stats. Yeah. But usually not even that. I guess where I'm getting at is it seems like online dating. We're dating things in our imagination. We're holding people up to standards in our imagination. Right. And we're getting advice, as you said, you know, people are doing it for clicks and

likes, but they're dispensing nonsense very often. Right. I'm, I'm so curious if this is, it's clearly not a new experience, but is it exaggerated? Have you noticed, I want to know the frustrations you hear from people why their relationships aren't working. Yeah, I mean, like, I think in your case, I would imagine for you, people are probably pedestaling you and they have an idea of who you are before they meet you. So meeting people online, they're not, they already have like almost like a fantasy version. I always advise my clients, don't look them up because you're either going to pedestal them or you're going to judge them. So I mean, don't do that if you can. But I think there's a lot of other frustrations and I think there's different ones I hear from women and I hear from

men. So I feel that the women are saying a lot of the times the guys are talking too much. And I try to explain to them that sometimes a guy is talking a lot. Maybe it's because they're narcissistic, but sometimes it's because they're nervous and they're trying to impress you. And I really advise people if you felt a connection of five out of ten, if you had a good time, you go again. I don't think the first date is meant to be like, are they going to be my future baby daddy? Like, stop that. It makes you future trip. Too much pressure.

Yeah. It's just a vibe check. And that is why a coffee is totally okay. Which is like that charming interaction at a museum before you go the first date. You have to treat this like the charming interaction. Exactly. That's very good advice. And then if that was good, go again.

And then it's not until the third date to about 20. I call it the evaluation stage where you get to know someone and you see like, is there an alignment of that? Like those sorts of things, but there are things that you can only tell through experiences with that person. So I do think it's a great idea to go on that weekend trip. See how they handle stress when something doesn't work out. Meet their friends. Before you jump in and be in your mind of like, I'm committed to this person because they're so great. Or not.

Allow, yeah, allow that time. And I think for some of the guys, like, they're finding that they don't know, like, do I, do I kiss them? Do I don't? They don't know the rules of engagement anymore. And there's a lot of ghosting going around. So, yeah, the behaviors are a little off. I mean, like if you go on one date and it doesn't work out, fine. Fine.

I don't, fine. But, I mean, I hear about six-month relationships where somebody just ghosts. For sure. It's a lack of ability to deal with conflict. And it is a reaction that they probably have had since childhood. I think that even with friends, like looking at these little data points of, of people who avoid problems. When there's an uncomfortable feeling,

instead of having a conversation, they avoid it. That is very telling of how they're going to behave when a bigger thing happens. Okay. Is there a cure for avoidance? Asking for a friend. Yes, there actually is. So the newer research on attached.

Notice on my body language. So there's newer research on attachment and that at any given time you're on a spectrum of anxiety and avoidance. So before the idea was like you're in a bucket and that's just where you are. Yeah, which I've, when I evaluate myself, it's of course complete madness. I'm a spectrum of things that changes, depends on the person, depends on how much sleep I got. I mean, all kinds of things. I could waft in and out all the time.

So if you date someone who has a very full life, right, and like their idea of love is 50% of my love I get from my friends. 50% I get from my romantic relationships, which seems to be more of the world you are in versus a codependent relationship, which is 100% of my love I get from my romantic partner. That won't do well for you. That will make you run for the hills. But someone who's got their own life going on, and then they're not constantly at you for more energy, more time. That will probably make you, your nervous system ease in and want them a bit more, right?

And so like what you want to do is like people who tend to have higher avoidance, they're really good in the first three months, right? Because you're intoxicated. There's the threat of like someone getting too close isn't there yet. And usually it's around the three month mark that something shifts. And what will happen is you'll find it in perfection. There's something that will make this relationship not viable for the long term. Is any of that resonating for your friend? Yeah, yeah.

Based on the conversations we've had, some of that is true. but all of it. Right. But some of it is true, for sure. The experiment for a friend who does that is to challenge yourself knowing this is what's going to happen. And it's a very natural reaction where your nervous system is freezing and wanting to run because it doesn't feel safe.

And you want to communicate like, hey, I'm feeling a little bit flooded and just try to have that conversation with that secure person and stick it out. Stick it out for another three months. tolerate the discomfort and you will move through it if you are with a partner who is secure enough to deal with it. I did something recently for the first time in my life. So because I, the ADHD doesn't help, right? Right.

Because with ADHD, I'll fixate on something, I'll hyper focus and I'll give, I'll accidentally love bomb somebody which can feel great, you know? And so I'm responsible for giving a ton of energy and so when they reciprocate, I'm like, pressure, but they're just reciprocating my energy. the opposite happens with ADHD, which is I meet them. I can't wait to, and then I forget that I forget to call them. Two weeks will go by. I'm like, shit, you know?

But what I did something recently for the first time ever, which was lots of high energy, really like each other, going super well. She starts reciprocating with tons of love and energy and attention. I'm like, absolutely not. This is not going to work. I, you know, I was like, we've only known each other a few weeks and you're trying to lock me down and make me your husband. I'm not ready for this.

But what I did was, and literally, she was texting me every day and sending me pictures. She was on vacation and she's sending me everything she's doing. I'm like, I've known you a week.

You know, it's like, I don't need all this, you know? And so I called her up. I said, I have avoiding tendencies. I said to her. I said,

and so when you give me all this attention, it's pushing me away. I said, you're not doing anything wrong. Yeah. I said, I said, I understand that I gave you tons of attention. I understand that you're matching my attention. And my reaction is nothing to do with you.

I just want you to know it's happening. And I want you to know that I'm going through this because I have these avoidant tendencies. And I simply just took full accountability, didn't blame her behavior, didn't make her wrong, and just took total ownership over my reaction to what was happening. And the fact that I played a part in creating the environment

that would make it feel safe for her. to love bum me back. And it was great. Yeah. Yeah. And I think what you did is super helpful, because what typically people do when they feel that pressure is they avoid. And it's a very natural human reaction for someone to spiral when someone was giving you attention and suddenly it's like one word answers or now it's two days to reply. And in their spiraling, their natural reaction is to go run and get it. Right? So I have. have a lot of clients who spiral and they're like, I'm going to write this message. I'm going to, I'm like, please, for the love of God, send that to me. Do not send any communications while you're spiraling.

And I get them to get into a calm place before they do any sort of communication. But it is, I think, letting someone know, even if you have more anxious tendencies to be like, hey, just giving you a heads up, this is kind of what triggers me. I'm not saying this is your responsibility, but I would just want you to understand. It's information. Yeah. It's information. Instead of doing a straight ad read, we're pioneering something called an ad with authenticity.

We want our ads to have valuable content for you, the listener. And this ad with authenticity is brought to you by SAP. Too many people think the way to build a career is to keep getting better at what you're already doing. SAP's David Robinson has learned that some of the most valuable growth happens when we go do the thing we've never done. before. I came to SAP, I was in product engineering. I was brought in to work on a new strategy for the company relative to composite applications and the deconstruction of the ERP. Whatever that means. I'll trust you that that's very important. It's super important and very exciting. Yeah. And I remember I was I was with someone at the time and said, you need to get out of that

organization just for a period of time and rotate into a customer success function. You'll learn a lot, you'll learn about the mechanics of the business, how important it is to balance both product engineering with the successful sales and delivery. He said the hardest thing that you'll have to decide is if you're successful is going back. At the time I thought they don't know what they're talking about. Spot on. That's exactly what happened is that you never really go back and what's curious is that we almost,

those have been at the company a long time, we're almost a connective tissue that the customer appreciates. But we did it differently in 1996. Like the CIOs keep changing. You're the consistency. We're the consistent. Exactly. It's really,

it's unexpected. But we're certainly a, we're a level of consistency, of predictability that a lot of customers have been longstanding customers have come to also trust and value. Situation ships. Yeah.

Very popular. Yes. Yeah. Are they a new situation or do we just have a name for them for the first time? I think we have a name for them for the first time. People have been casually hooking up for a long time. However, I think right now it's being amplified because the apps make it super easy. There are no social consequences, right? Before, if you met through colleagues or a family, like, there's social consequences if you don't behave properly. But now that's out the window. And I think that people are less committing.

They're not committing as much. It's really, really hard, especially for the younger generation, to commit and then feel the uncomfortable emotions and those hard conversations and move through it. Why?

Just stop it and find another person. And that's what they're doing. Because it's easy, right? Again, if you can shop for a new... It used to be hard to meet a new person. There was some risk with breaking up because you have to start again and how am I going to meet somebody and, you know,

but now, the shopping is so easy in fact very often people will start before they've broken up see what the options are sure so how much of what we're talking about you know and I see it in work you're seeing in relationships how much of it is simply people being uncomfortable with discomfort and the how much of the advice that you're dispensing is really people learning how to be uncomfortable how to move through discomfort how to manage discomfort how to communicate discomfort yeah you know how much of it is is just that

Yeah, I mean, those are basic relational skills, but, you know, I just saw some research on how in Gen Z their top value is self-care. And I, if you look on the internet, everything is about like self-care and like, you know, like your mantras and your macha. Anything meaningful in life, building a career, a business from scratch, a loving, intimate relationship that goes through ups and downs where you're each other's rock, there's not. There's moments where there's no self-care at all. And for a season, you just have to like suck it up and be committed to the thing that you've, like, that you're trying to build. And I think that is a muscle. And I think that is lacking in a younger generation.

And that really does worry me. And so when people are wanting to get in a relationship, I think you also have to understand, like, what is their definition of commitment and love? Because if they're just about the feelings of being in life, love, that relationship is going to come to an head between 12 months to 18 months when the love chemicals take a nose dive. When I look at my favorite couples, and I have a few of them, I know who they are, like the couples that I like, I want a relationship exactly like theirs, like my God.

And it's not all unicorns and rainbows, you know, by any stretch of the imagination, but they have dynamics and they have levels of trust and they have protected each other's independence in ways that I find quite magical. If I ask any of them, what's your secret? They all say the same thing, which is we do the work. You know? And I think people forget that relationships are effort. Yeah.

And that scares people like, what do you mean I have to do work? Yeah. And what they're forgetting is that if you're on the receiving end of that effort, it feels really good when somebody's willing to do the work for me. Yeah. And if it's mutual, oh my goodness, what a magical thing that somebody's willing to be on uncomfortable, sit in discomfort, move through pain, not abandon, give second chances, give benefits of doubt. You know, all of these things allow personal narratives not to take control of the relationship,

fight to get to resolution, abandon ideas of who's right and who's wrong. All of these things, it feels incredible when somebody does it for us. And what I've learned about relationships and what has saved me and made me a better, a better boyfriend is I no longer view relationships as what can I get from a person, but rather what can I give to this person. I think what you've explained when you talk about the friends that you have that have great relationships and the ups and downs and the working through it, you describe a great relationship. And I think a challenge that people have today is this mindset that they need to meet the perfect person. first and then it'll be great. It's like as if the perfect person is going to land on your lap on date two and you're like, oh my gosh, like this is it. And that's just simply not the case. Like a great relationship is earned and it's earned through going up and down and seeing their flaws and that

they leave their socks on the floor and it's so annoying but like you work through those things. We need to meet people who are good enough and then we jump in with two feet and then through going through the stuff. It's the hard stuff when you're there for each other that it goes from good to great. And I don't think that a lot of people have that mindset. This explains your whole attitude, your whole point of view around dating,

explains why arranged marriages have a lower divorce rate than chosen marriages, because they show up, not because of the swipe, but they show up knowing, okay, let the work begin. Is that, I mean, what is your theory as to why arranged marriages do better than chosen ones? Well, it's commitment. And we know, like, through the paradox of choice, when you have so many choices or if you can refund something, you'll actually be less satisfied with the thing that you bought.

And right now, like, we don't have to get married anymore, right? Like, I think when we look at our parents' age, there were a lot of things or institutions that kept a couple together, or you're having things. family. We know now, like, it's not taboo to not have a family or to get married. You can go habitate. You can not. And those things that would keep a relationship together, which will make you go through the uncomfortable times. And, like, I have to abandon my own self-care during the season. We don't have that thing. So why are we together? Just for vibes? And so if the vibe isn't vibing, I'm out. So much of this is mindset, isn't it?

I think it's mindset and it's like... It's like your attitude towards. I think it is a maturity of looking at relationships and relationship skills. And, you know, I have, I had a client, a friend yesterday who like wants to be my client. She's like, Amy, like I really, I'm ready to start dating. And she has it in her head that like she needs to date a very, very wealthy person. And I was just trying to like go through. I'm like, do you really need that?

And I was like, you're actually not ready. And the reason I know that is when someone is ready, actually open for a relationship, what they tell me they look for in a partner is not those shiny qualities. They're like, they're looking at, are they kind? How do I feel when I'm with that person? And when someone is just like, they need to be this tall, they need to be this age, I'm like, you are operating from your ego. And that is okay, but this is not your season right now.

to get serious about a relationship because you actually don't want one. Because your behavior is contradicting what you say you want. Situationships. I want to go back to situationships. No, no, no, because I think they're pervasive. And in my experience, they were girlfriends. We broke up and then never really broke up. Okay.

We were no longer boyfriend-girlfriend. We technically could date whoever else we wanted. But we were just in this sort of limbo, nice space of spending a lot of time. together, sleeping over, you know, these lovely situationships that were downgraded from the relationship we had, but never re-upgraded? Like, why are they, why are they bad or wrong when you have two consenting adults? They're not bad or wrong. However, typically what happens is one person wants more. So, and usually they don't know that until the other person finds someone else. Oh, got it. Because the situation ship is safe. It has all the trappings of relationship.

For sure. It has the guise of security until one person finds someone else to date. And all of a sudden you realize, oh my God, I've just been broken up with them. Right. And then you're dealing with a breakup all over again, right? Because in your body, your body doesn't know that there was a breakup, right? Those neural pathways never had a chance to print away. And so I work with those clients.

Because there was no breakup that happened. No. Babe, we're breaking up or somebody cheated. It's like they did nothing wrong in finding a partner. a new partner. You can't like, so there's no transition period from, this is romantically over, and then we're coming back to it in a different form, right?

Your body, they're like, we've been together this whole time. So when one person in that situation find someone else, you're just breaking up like it's square one. And there is nothing wrong with it, but you have to also understand, like, if you are doing that and you say you want a relationship, say you want a family, you want to get married, or whatever that is, is your heart actually open? Or is that real estate being taken up?

And we justify, oh no, it's totally fine. Yeah, yeah. So what we're saying is they're not inherently wrong or bad, but they do come with risk. They do. They come with risk of heartbreak if the other person actually does choose to find somebody. You could sit in a perpetual situation. Or, to your point, that if I truly want a committed relationship, then I have to speak up about it because this isn't it. and my real estate and my heart is being taken up.

In other words, I'll never find the thing I'm looking for because it's leaky energy. This is a term I just learned. Oh, yeah. Leaky energy. Yeah. I kind of like it. Yeah.

Kind of like it and I kind of don't like it. I like it when I'm talking about other people. What is leaky energy? There's two definitions of it. So one, leaky energy is when you are just, maybe you're in a relationship, but you're super flirtatious with this person or you're liking people's Instagram.

There's like little micro-cheating. You're just getting that validation from a lot of people. And you're not even aware of it. And there's like a trail of people in your dust of like, is this person into me or are they not? And that does have an impact into your primary relationship, even if you think you're being innocent. So that's the definition I operate on for leaky energy.

It's just being aware of how your energy is coming out and the root of your energy on like you could compliment someone, but is that root of that compliment to like get validation and to start having some back and forth or is that really like a generous compliment? I want to unpack this more because there's nothing wrong, especially if you're in a long-term relationship with finding other people attractive. For sure. Looking down the street like, oh, she's cute.

Yeah. You know, your girlfriend goes, oh, yeah, she is cute. Yeah. Like there's nothing wrong with that. Yeah. There's no intention behind it. And so if you're on Instagram just swiping around and, you know, you're doom scroll and you like something for no reason and you click like, can you keep scrolling?

And if it's, you know, some girl in a bikini and you click like or some, you know, whatever it is that you're into and you click like, is that leaky energy? So I think it depends because I have clients who are like upset that their boyfriend is like liking a bunch of Instagram models, right? So if that guy is liking all these Instagram models because there is deep down an intention of like maybe they'll open up a conversation or DM, that is micro-cheating. Right. If that is like, oh, cool, like I like her yoga pants, whatever it is.

And it's genuinely coming from a place of like, I'm not trying to microchete. That's different, right? The same action. How can you tell the difference? I think you have to look within yourself. You only you know. Okay, let's change tax here. Okay.

Okay. Have you found love? I have. Yeah. And how long have you been dating? Seven years. Seven years. Yeah.

And you didn't get married. No. We will one day. Yeah. So what changed in you that after two years you were gunning for the ring and after seven years you're chill? I feel very secure and safe in the relationship. And I feel like before when I dated people and I wanted the ring and the wedding, a lot of that was because I didn't feel secure and safe in the relationship.

So I needed that to lock it down. And what about you makes you a better girlfriend than you were. I am in a relationship where I have had emotionally corrective experiences because I feel very safe with my partner. So even though I'm a relationship expert, I've still had like all of these old patterns that kind of awoke once I got in a relationship. Because when I was single, there's not a lot that can trigger you.

You're like, oh, a little of anxiety, but it's when you're in a partnership. And I just remember, like, not even that long ago, we were at a cafe and he, like, gets on his phone and goes on his email. And I flipped. I was so mad. And I gave him, like, the silent treatment for two days. And after I was like, oh, this isn't normal. I'm having a disproportionate reaction to the offense. And I had to look in.

And I'm like, oh, wait, this was because when I was, like, in kindergarten, my, like, my mom and dad would, like, forget to come get me. and I would be waiting for 45 minutes and my time was never seen as important. And so now old Amy, like this tiny thing triggers this big response and I brought it up to my partner and we had a conversation and I apologize for how I used to also react, which was pout and cry. And so like now I'm aware of that and I don't win all the time, but I can use my words and my silent treatment gets less and less. You used a term that I've never heard before,

emotionally corrective experiences. Unpacked that for me. Yeah, it's a term used in therapy a lot where it's in relation with another person where you can actually get triggered and it's an opportunity to almost course correct the old pattern or wound. And so now in a safer environment,

you're now not just an eight-year-old adapting and trying to survive. You're with someone who you can trust. So the reaction to behave how you used to can come up, but you can talk to that person. That person isn't going to yell at you or ignore you. And you move through it and you're like, oh, it's actually okay. And the more you do that, that old wound that used to trigger an outsized reaction starts to get smaller and smaller.

It's a process. It's a process that happens in relationship. And so that means both parties have to be open to the idea that you won't find the solutions up to one infraction, but rather, as you said, the silent treatment gets shorter and shorter and shorter. What's frustrating about this conversation is it seems like, why can't we learn these damn lessons? It's the same themes. It's, you know, it's learn to communicate. It's take accountability. It's, you know, learn how to sit in discomfort.

Like none of this stuff is new. It goes back since, you know, the dormant of relationships. you know, why are we still having this conversation in, you know, 2026? I mean, I learned how to dissect frogs when I was in school. I didn't learn how to communicate or use nonviolent communication to, like, express my needs, right? Well, the good news is now you dissect frogs all the time. That's a valuable. You don't need communication in your modern adult life.

You need to learn how to dissect frogs. That makes perfect sense to me. Yes, yeah. What, with all the talks people you're talking to, what is one of the, you're talking to, what is one your constant frustrations that no matter how much advice you give, no matter how much guidance you give, coaching you give, this problem just keeps rearing, like, it's just a perpetual frustration for you in the advice that you give. I would say the amount of priority people put on instant chemistry.

And this thing that like you're attracted to who you're attracted to. And they can be drawn in by someone who has shiny qualities or fits their idea of a type. But we know that through hedonic adaptation, we adjust to those things. We adjust to their height. We adjust to their income. We adjust to, I don't know, their waist size. And that thing that drew us in that made us so excited, it goes away in like two years. So what's left after that?

It's the quiet qualities. And research also confirms this. It's the quiet qualities that can predict if a relationship will be happy or successful. And it's how committed is your partner to you? How appreciated do you feel? How well do you handle conflict together? And that might not show up on a second date. And so I think there is, I'm very optimistic about love.

I think that there are a lot of viable partners around us all the time. I think one of our main problems is we have blinders on because we are over-emperienced. emphasizing the things that don't matter in the long term. But it's easier said than done, right? I'm listening to you. I'm going, yep, yep, yep. But how do we change our mindset to not focus on those things? Look past those things in a world that is bombarding us with those things.

Yeah. I make my clients go on a dating experiment where they have to date nine different people, totally outside of their type. Because every I tell them, change your type. logically maybe go through one ear, go out the other. But if I'm like, okay, I have a client who has like a six foot height requirement, one of the people they have to date is someone shorter than them, right? I'll have a client who's like, I only date people 25 to 29.

I'll have them date someone older than them. And the way they do this experiment is they can't get into a relationship with any of them. So it changes the way that they date because there isn't that pressure of finding the one. They're just like, I'm just doing this experiment. And at the end of the nine people, you can look at who was the best in terms of your benchmark, right? You can go back to that person or you now know in your future dates, what type you're looking for. Is that communicated to these nine people? Because it's a little mean to go on date.

It's not communicated until it goes a little bit deeper. And then someone will say something. Okay. Because it's a little bit mean to set up expectations like, I'm on an experiment date, but you're going to fall in love with me. Well, no, but here's what happens, right? So a lot of the people who finish this end up getting in a relationship. They don't finish it. And they say the exact same thing to me.

They're like, Amy, I'm with someone. I would have never given a chance to. And it is human beings were drawn to what's familiar. So if you are familiar with the guy who's just a little bit unattainable, you're constantly going to be attracting and being drawn to that emotional experience. So the experiment makes you be in situations. where, oh, like, I'm now prioritizing kindness and other things I never did before, and you get familiar with how that feels like.

I know why a lot of my relationships for many years failed. I had a bad picker. I would date the wrong kind of person over and over and over again. And for various reasons. But I recognize that I had a bad picker. They're good people, but they're not for me. me, you know, and I'm not for them. But I kept finding myself dating very similar personality profiles over and over and over again. And it was a big deal for me to recognize that. And it's

hard to break. Yeah. It's very hard to break. Yeah. I really like talking to you, like, you know, because I can't help but filter everything you're saying through my own experience, of course. And I'm soaking as much as I can. Um, there's a, there's, there's, maybe it's just because it's broadcast on on Instagram and TikTok but there seems to be more skews younger but I think that's just because they're broadcasting out of Instagram

and TikTok all the people just out broadcasting their experiences as much but there seems to be more people who don't know how to date forget about being in the relationship there's one person that I follow on Instagram whose content I love and she's

super affirmative and like like just great advice giver just just a good good kind heart who spreads a lot of positivity which is what I like and every now and then she'll post a video how she she's never had a boyfriend she barely dates but young attractive successful you know doing well in her in her online influence her life what that's worth that's a different conversation um and there's a sadness that this person who's in her mid to late 20s, hasn't, forget about love, forget about a relationship,

it's barely dated. Yeah. And that seems to be more and more common. I'm meeting people in their 20s who've never really had more than a couple of dates here and there. What's going on? And I'm asking for the people who are listening who are young, but also for the parents of young people.

Yeah. A lot of social skills have atrophied. Some of that is due to the pandemic. A lot of that is anxiety. And so the idea of going out in the wild at a coffee shop and approaching someone and risking rejection or someone not interested in you, there's so much anxiety of doing that. So why would I bother? I would rather just doom scroll or I'll do this other thing that will give me a hit of dopamine. And you do that enough times and then you just don't.

don't ever do that thing on meeting someone in person or having the conversation. And again, I do think this is there's a message that we need to avoid the uncomfortable feelings and bad feelings equals bad. And so they're not. You can get rejected and it's okay. Let's double click on that. Let's double click on that. That is so good.

Bad feelings does not mean it's bad. Yeah. Right. Uncomfortable doesn't mean narwhatever. narcissistic or toxic, just means uncomfortable. Yeah. All the advice that we're getting is about mitigating, blaming, letting ourselves off the hook.

And very few people are giving us advice to enjoy, and I mean enjoy, discomfort, anger, depression. Depression is only a bad thing if you get stuck in it. If it's capital D depression, that's a medical condition. it's perfectly normal and healthy to be sad. Yeah. That it's part of being human to be messy.

And you can't be happy every day. And I think the thing that I've learned as I've grown older, which is I saw negative feelings, bad feelings, as somehow making me weaker. And that if I was happy and optimistic all the time, that makes me stronger. And what I've learned is, no, what makes me a great human being

is that I have a range of emotions. I learned this in a funny way. I'm an art collector. I collect a lot of art, as you may see. There's a ton of it. And I bought a sketch of a dead bird. And it showed up in the mail, and I unscrolled it. It was all rolled up in the tube, and I unrolled it.

And I had instant buyer's remorse. Like, what the hell do I want with a picture of a dead bird for? Like, I'm not going to hang a dead bird on my wall. You've got to be kidding me. And I was like, what have I? I done? Like, why did I buy this? You know?

And by sheer luck, I had a friend over when the mail arrived, who's an artist. And I'm expressing all my buyer's remorse. And she looks at me and she goes, a good art collection has a range of emotions. Ooh. And in that moment, I fell in love with my dead bird, had it frame, and it hangs very proudly on my wall. Because my art collection has a range of emotions. And this is what I've learned about great human beings.

You're getting me thinking. I'm connecting a lot of dots and seeing all these connections. But what I'm taking away from this entire conversation with you is the skill, the single skill that we all have to learn in order to succeed in dating and to succeed in relationships is our ability to sit in discomfort. And the single best way to manage discomfort is to learn how to communicate. Yeah.

That's my takeaway. And I'll add on top of that is to be aware of the, story you're reinforcing. Yes, the reframing and the mindset. Yes. Because whatever you keep repeating, right, you go and you approach someone at the coffee shop or you DM and you get rejected. And then suddenly it is, oh, dating sucks in L.A. Right? Or these people are like this. And you keep saying it over and over again or I'm an avoidant. I'm always such an avoidant in relationships. That becomes your narrative and your identity and your future. Really good.

Not I am an avoidant or I have avoidant or anxious attachment, but it's not a diagnosis for heaven's sakes. Exactly. It's I have had avoidant tendencies. Yeah. I like that it's, you know, I have had avoidant tendencies, which is it's a past pattern.

It's not who I am. Exactly. Yeah, yeah, yeah, yeah. It's not a predetermined. It's not predestined. It's not predestined. Yeah. You're really good at what you do.

Thank you. Good stuff. Amy, thanks so much for coming on. Thanks for having me. This is so fun. Absolute joy. I have to do a 10-part series of this. Went on for a long time.

It was really good. As always, thanks for listening. And if you liked this episode, please do remember to subscribe to A Bit of Optimism wherever you enjoy listening to podcasts. And remember, new episodes drop every Tuesday. A Bit of Optimism is a production of the optimism company,

lovingly produced by our team Lindsay Garbenius, Phoebe Bradford, and Devon Johnson. And if you want more cool stuff or just to find out what I'm up to, visit simoncic.com. Until next time, take care of yourself,

take care of each other.