IMO with Michelle Obama and Craig Robinson - Dating Should Be about Pursuing Joy with Tracee Ellis Ross

Episode Date: April 16, 2025

Actress, director, producer and businesswoman Tracee Ellis Ross joins IMO to answer a listener question from a man who has been unlucky in love but wants a partner and family. Tracee discusses how she learned to embrace being single for much of her adult life, why she feels ready to date again, and shares her dating checklist. Plus, Craig offers his thoughts on what men are looking for in their dating lives.Have a question you want answered? Write to us at imopod.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

You know, it's sort of innocently sweet and it's not so hard over the head. Like, can you stand alone in a room? That's why I like the question, because I would ask that all wrong. Right. That's just the thing. I would ask that same question. Are you an insecure trifling ass? That is exactly right.

Are you so insecure that you can't handle a strong? I would ask it all wrong. He would be swung from a start. I am a boss. I'm a boss. Are you okay? Be in the belly. Can you level up?

Can you level up? And then he's running away going on. She's aggressive. How you doing? I'm doing great. You know, feeling good. Another day. Alive.

We're getting to that age where, you know. No, we're not. I'm just blessed. Woken up. Got up. You don't think we're at that age. You're older than me. Well, we are.

Yeah. We weren't in our 60s, my friend. I know. But I'm hoping I got a good. good 20 more left. That's what I'm shooting for, at least. But, you know, we're at the age now where, you know, it's not so tragic. I know. Well, did you get enough rest last night, old lady? I did. I, you know, the girls came over for dinner and I was so tired that I left them at the table, which is unusual because I love hanging out with my girls, but I was that sleepy. I was like,

you know what? Mom's going to bed. You can sit here and talk to your dad. So, so, but yeah, I, I got to bed early and had plenty of sleep. How's your Airbnb feeling? Oh, my gosh. Still happy with your situation? I'm so happy that I did not go to dinner last night. I left here. Just to stay in your Airbnb house.

Just to be able to chill in my Airbnb in West Hollywood. And guess who visited me this morning to do their laundry? Who? Leslie. You know, my daughter's in town here and she came over to bring her laundry to do. I mean, that's why I like. Why does she have laundry? How long has she been here?

Because she works out every day. Oh, okay. So she had a whole bag full of gym clothes and underwear and stuff and just put it in. And I was like, yeah, come on over. And then we had breakfast. And then she went to meetings. Yeah. And I think she's going to come stay with me tonight.

I'm learning a lot about the Airbnb life since we don't do that. Since you don't get to do it. But the girls do. Yeah. We and Sasha, whenever they're traveling. And so our kids, Avery and Leslie and Emily and Elena, they all, they have no qualms about. Let's go. Let's find a place. It's really a different intergenerational use. I mean, young people, they like being in a home. Well, a lot of times when they're traveling, they're sharing with their friends. They're dividing up a house. And, you know, so. And I find I've gotten to like it now. So, you know, I was a strictly hotel guy. I wanted maid service every day. I wanted to be able to go down to the bar and not have to drive anywhere. I wanted all that.

stuff, but then the amenities of having your own place that's like a house and you can sort of live the way you normally live is much more appealing. Well, it sounds like it'd be a good girl's trip, a friend gathering session or, you know, it's a little, little, but anyway. Well, I'm glad you are comfortable in your Airbnb, mister, so you'll never stay with me ever again, I guess. No, that's, it's, it's, it's, it's, I would not do that. Have we been displaced? You have not been displaced. You have not been displaced. But you might want to come visit me every now and then now when I'm in town. Would I mess up your mojo if I showed up with my motorcade in your house, driving up the driveway with... It wouldn't mess up my mojo. Might mess up the owner's mojo.

It might not mess up. Well, maybe. Maybe I'll stop by and see all your many pools in your house. Yes, yes. Well, what are we talking about today? So we're talking about dating today. And I love talking about dating. Because I haven't done it in decades. And, you know, when we were preparing for this, I was asked the question, when we were younger, did we talk about dating? And I have to say, I don't remember talking about dating much at all when we were younger. I felt like I was way more in your business.

and I kept my business to myself. Yeah, but I didn't have much business. I mean, just think about it. I had to be fixed up on my junior prom. I mean, I didn't have any, I don't remember having real girlfriends. Oh, that's the problem with. So with you and these sports, it's like, yeah. Spend it too much time in the gym.

Yeah, yeah. It really was too much time in a gym and focused on my school work. And then I just wasn't the dating type. But it's interesting because, all right, so this is the benefits of being the sister of a guy who plays sports, which is one of the reasons why I enjoyed going to your games. It's like most of the guys I dated were on the JV team. So me and my friends, we'd show up at the game. So I don't know why you couldn't find a date because I think my first several boyfriends were your teammates or they were. younger on the JV team. Yeah, they were younger versions of...

Because that was always an important test was, well, what do you think about them as a teammate? You know, are they, first of all, are they good at basketball? So I generally only dated the people that you said were actually good, you know? Also, you and you had this theory about, you know, knowing a person by their on-the-court behavior. Yeah, I can't take full credit for that because I really got it from dad. And what my dad would say is you can really tell a person's character by how they play pickup basketball. And the reason is you can see how hard a person works. You can see if they're the type of person who talks trash.

And I've told this story many times about when you first started dating Barack. So Meish starts to date Barack. And we don't know who this guy is. We just like Barack. Who's got a name like Barack? And I was, and I'm thinking of myself, it's going to last about a month like most of your relationships did. That's that true. And I've had many a long-term boyfriend.

I wouldn't call those guys' boyfriends. Oh, my gosh. See what I had to go through. You didn't even call, you didn't even want to call my boyfriend's boyfriends, none of those guys. But anyway. Anyway. So Mish pulls up to the house and we're sitting on the front porch waiting for her to bring Barack. And she gets out of the car.

And I remember mom's first thing was. oh, at least he's tall. That was her first thing she said, because Mish was usually posting up her other boyfriends. She said, at least he's tall. And I said to myself, well, it's too bad it's not going last. But the best part of it was after we met him and she had been dating him for a little while, she said, would you mind Craig taking him to play? And at first I said, no way, I am not doing your dirty work for you. If he turns out to be a bad dude, I am not going to be the one to say. And you say, come on, please. And I finally acquiesced. And so we went and obviously we had a great time playing. And what did you learn about? This is what I learned. Aside from the fact that he is

tremendously left-handed so he couldn't go right at all. Most importantly, he was a team player, right? Like, he fit in with the people. And so I was able to report back to you. Everything was fine and the rest is history. So anyway, we got off the subject. And, you know, another one of the reasons why I didn't date was I went to an all-boys high school. So it's not like girls are walking down the hallway and you see one like, oh, want to go to movies.

or something. It was like crickets. Yeah, but you, you know, you're just an all-around nice guy. You weren't shy, but you definitely weren't, you didn't have some lines. And I think that that's what we wound up talking about. It's like, you got to, you know, you got to get your game on. Yeah, you did say that. So, you know, I think the politeness of you, you had to wait to hear that somebody had a crush on you or was interested in you.

I think you never assumed that. Right. No, you would have had to hit me over the head with the fact that somebody was interested for me to have the nerve to ask them on a date. Yeah. And for your friends at this stage in life, you know, forget high school, college,

because, you know, you're just doing what you're doing then. Yeah. How do you think your friends think about selecting, dating? Here's what I will say. And I am dying to get our guest out here because she's going to be able to help referee this between you and me. But I will tell you. I don't know if it'll just be between you and me. I think guys in my generation when they were dating, they ended up marrying the women they were dating when they were ready to get married.

Yeah. It's like musical chairs. Exactly. Just like, okay, the music stopped. I'm sitting on your lap. I love you. But what I will tell you is we all ended up getting divorced. And once we started dating again, much more discerning.

When I met Kelly, I was not interested in a relationship, not even dating. We just happened to be talking to somebody at the same time. So I'm making a long story short. But the point is, once we see. started dating. We said, I said, let's figure out if this is going to work or not work. So we said, listen, let's go somewhere where we can figure out if this is going to work. So we went to San Diego, the place we always go to, nice big house. It's like, you have your own bedroom. I have my own bedroom. If it doesn't work, we just say, say la Vie and have a nice

weekend. I said, bring your list of things you want to talk about. And I brought my list and my list does 30 different things. 32, 32 things that I had individually that one discussed. 32 items. 32 items. She had three. I was like, this ain't going to work. Oh.

But after we went through my 32, you know what she said? What? All of yours fit into at least my three categories. I thought I was just doing categories. I wasn't doing the things. I think that would have been a reasonable thing to think. I was, I was, I was, I was burned. You go from like, I didn't ask any questions.

I was just ready to get married to a list of 105 steps before. But that, well, it worked. It worked. Because now, I mean, you know everything. I knew everything. She knew everything about me. And so it worked out. Thank goodness.

But let's bring out our. Yeah, it's time. Yes. And I almost feel like I don't even want to do a formal introduction because this is one of the first times we've had on this show. where the guest feels more like a family member. She's just so sweet. She's got manners. She's so sweet.

She's got manners. She's funny talking about being fun. She's funny. But she's an award-winning actress. She's a screenwriter, a director, an entrepreneur that I want to hear about this. You don't know about pattern? I guess not you're bold. Okay.

I'm sorry. I forgot. Oh, man. You let me do my job. I'm sorry. I'm sorry. I indirect. And so without any further ado, Tracy Ellis Ross.

Tracy! I'm so good. I do feel like family. We got family in the house. Really interesting conversation. And I took some notes. I took notes in my head and I actually wrote them down out there because you said there's a lot you can learn about how. who a guy is or who a person is, by how they are on the court.

Yes. They let their guard down. They let their guard down and their character comes out. I think I could have used that information. I think I'm a little late on adding that to my list of how to figure out if he's a match. Noted now. There's still time. There's still time. There's still time. You know, there's still time.

You're breaking his hip trying to play basketball. Yeah, I know. It's got to be a different measure now. I know. You know, I made Barack put his basketball shoes up once he got his lip busted. Right. And he was in the White House playing a pickup game. Yeah.

And I don't think many people realize this because he was definitely in shape, athletic. And I remember because you were at that pickup game. Yes. And I'm in the White House, actually in the doctor's office, getting an exam. So they're playing in one of the admin gyms. And we get the call. We hear that the agents are like, you know, we're in a game. coming back. There's been an accident, you know, and I'm like, ugh, because I'm always like,

be careful playing basketball. You shouldn't be playing now. You now have a real important job. Yeah, people are depending on you. Right. You know, and literally, he's coming in with a, you know, a goss thing on his, on his lip. He didn't need stitches or anything. He needed like 30-something stitches. I mean, his lip was, I saw it. It was like, he took the thing away. And I was like, your lip and he had some major speech. This was probably Saturday. He had some major speech on Monday. And I was like, this is what I'm saying.

You know, you're playing like your tin. And now your lip is split. So we digress. That's okay. That's all right. No longer can we, are we dating people? No, but I am. I was supposed to say.

I was like, Tracy, Tracy's, you know, my girl. Yeah. And I do bring. I bring stories home. Bring back to Michelle's on. I'm like, what? What's happened in the last several months? And it's always eventful.

It's always good. Well, the thing is, I stay open. I'm probably way open. Yes. Oh, my God, that sounded so wrong. I didn't mean that. Mom. My heart.

Your family. My heart stays open. Your heart literally stays open. Yes. Yes. Okay. All right. More open than it should be.

But I do date. And it's a fascinating adventure out there, you know. Mostly, though, I think there's really good men out there. I think to a certain extent, I'm a very unique sort of unicorn of a woman. And so it's going to take a unique person. And in the meantime, I have really learned how to live my life and enjoy it and not sit around waiting. I come, you know, I was saying to someone recently that I'm one of the first generations of choice and it's not anymore, which really, there was a window and that has shifted. And I do think that that's going to change dating.

for women so much. When you mean you've been the sort of the product of choice. Yeah, like the assumption of Roe v. Wade and the ability for a woman to find her own delight and pleasure and choice around how she navigates dating

or how one would navigate dating and we're in a different world now. And I'm curious what that will look like. It frightens me for younger girls because of many reasons, obviously, but even with the systemic protection of Roe v. Wade, I still was coming up against the cultural norms of being a choiceful woman

and owning my own body and my own choices and what it is that I'm looking for in a relationship and the ability to negotiate in a relationship what it is you want the relationship to be between the two of you as opposed to what society says it should be. And that's different. I don't know that we're going to lose that. I think women, we're used to having a say in our lives.

Yeah. And I don't know whether this, the whole movement is about sort of re-harnessing us, you know. Whether is it really about, you know, reproductive rights? Can that really work now that women are educated and we're being raised differently? I mean, the truth is that men fathers are modernized. Yes. Right? I mean, mostly.

Mostly? Mostly they are. And if you were to ask the average man, how are you raising your daughter? Because you love her. The average father that loves their daughter wants them to be excellent, you know, and they want them to have opportunity and freedom. And when you think about who, you don't want your daughter saddle marrying some guy that chose her because he just didn't think about anything else and was ready at the time. And who believes that her body is his choice. Exactly. So I don't think a lot of leaders are thinking about that. Yeah, well, and they haven't been asked to because I think it's not always a context that if it's an area that you don't have to think into. Right. But I think there is, it is a genuine regular thought process for me. It's one of the reasons, I mean, we've talked about this that often I date younger men. And a lot of it is because... Let's stop on that, folks. Oh, my God. We had a great dinner on that one. We had a great... dinner, by the way, where across the table your husband goes, but why? And I said, well, maybe because I can. Yes. Parish. This is what I'm saying, tales from Tracy's. It's fun. It's very

fun to share. Tracy Taylor. But one of the reasons, though, that, because I had to ask myself that question, I was like, what is this about? Yeah. Because I want a partner and so often, and it's not just that I'm older. I'm also very embodied. I am a very whole person who knows myself, who is in charge of my life, and who lives a very full, just robust life. So it's not just age. It's like life experience and sort of a difference. But I had to ask myself the question, why? Why does this keep sort of coming up other than they're hot and gorgeous? There's that. There's that. But a lot of men, my age, are steeped in a toxic masculinity and have been raised in a culture where there is a particular way that a relationship

looks. And anything that starts to smell of that for me, I am, I did enough of it where I was controlled and felt like I was a possession or whatever those things were or prize or, and I just, I have no interest in it. And I will not do it again. I'm sorry. No, I was going to say, so it's a generational thing. So it didn't matter how you met them or is it just kind of a guy's a meeting? That's obviously, it's a generalization. But But because I have dated men my age, there is a difference. There is an openness that occurs with a younger man around whether it's gender fluidity or not even having an issue with homosexuality.

I mean, something as basic as that. Right. Yeah. I hear you. Or I'll be, you know, sitting across the table from somebody and just like, what did you just say? What century are you? Like, oh, my God. Where's your horse and buggy?

Yeah, like, I'm so sorry. And your bed pan. Yeah, for real. Chamber pot. Yeah, your chamber pot, your chamber pot, like where I'm just like, yeah, this is not a match. And I don't, I have long been past the age where I feel like it's my job to teach somebody or grow them up. That I'm not interested in. So, but it's interesting. I mean, there's so many different philosophies on dating. And I have come up with mine. I have come up with what works for me and what makes sense for me and what feels safe for me.

Yep. You know, I mean, like I'm not on dating apps. I have friends that have great success with dating apps. That's just not something I'm comfortable with. So you're meeting folks in the wild then. That's the only way for me or someone sets me up or I meet them at an event. I meet someone. It's usually people that also have a level of recognition that they have as much to lose as me to a certain extent. I don't know. I mean, I haven't had great luck lately, but I do have to say I'm moving up on what it is that I'm looking for as a match.

Yeah. Yeah. I've had some doozies. Yeah. Yeah. But it's just, I just love watching. in your life because you were modeling so many things, the next phase, how many versions of ourselves we can become at all ages of life, you know, and how to build the life you want. Yes.

Not the life that somebody told you you were supposed to have. And let me tell you, I have, I told you this about the girls. And Tracy, just like, you know, she mentors the girl. She's always there for them. But trying to get, trying to make sure that I am not subconsciously sending them these messages about what their life should look like. Even like when you ask, are you dating anyone? I mean, that's something that we ask young people in their 20s, you know. The whole thing about weddings, you know.

We talk a lot about that. Yeah. It's just like the pre-proposal and the bachelorette and the pre-honeymoon and then the three wedding dresses and the, and, you know, have you thought about your 32 list items of who you want to marry? Or are you busy planning, picking out your photographer? Yeah, it's interesting that whole, I hope that that is starting to dissipate culturally. I really do. I think it, social media is perpetuating some of those things in a really big way. But I, you know, I did dream of my wedding growing up. And that's not to say that I didn't dream of the bigness of my life. But I could have spent a lot more

time dreaming of my life. And, and, you know, as much as grief does surface for me around not having children and not having a partner, I still wouldn't want the wrong partner. That's a great point for people to hear. I don't, I'm not interested in that. You have to make my life better. It can't just be, you know, I'm in a relationship to be in a relationship. So even though the grief does emerge and that comes and I hold that, I think of what I've done. And I think of, I woke up every morning trying to do my best. I didn't wake up one morning and be like, I'm going to mess this day up. That's right. So I must be where I'm supposed to be. And I don't know. Sometimes I think of all of the things I've done, the courage that I've had to have and what I've

had to learn how to navigate as a single person with no one to hide behind. And it's built. it's a really beautiful experience around me. And I have incredible friends. You do. Well, this is a good segue to get to our question, especially the talking about dating and meeting people. And we have a great question. So Natalie, our producer, is going to read the question for it. Make sure your mic works over there.

Is it working? I think we're good. All right. Yeah, we're good. I'm excited. Hi, Michelle and Craig. My name is Ronan, and I'm 41 years old. I've got a question about that big,

frustrating topic dating. More accurately, I should say how not to date. Let me explain. Throughout my 30s, I was in and out of relationships. One was very fruitful. It lasted several years, but in various respects of our lives, the timing just did not align, so we ended up splitting up. Since then, I found myself in relationships that have been very clearly unsuccessful. One woman's creative and professional interests totally matched mine, but we fought constantly. Then I was with a woman who was great. Our leisure interests were similar, her family was great, but I was just not that into it. Something was missing. Most recently, I ended up in a longer-term relationship that my friends at least would call toxic. We had great

chemistry, and I was really in love with her, but she struggled with sustained intimacy after a recent divorce, and as a result, I got myself caught in a pretty regular cycle of hurt. Since then, my dating has been a mess. I've been distracted by women. I simply find attractive, but who otherwise clearly are not a match. And in the meantime, I still find myself thinking about my last relationship. So this brings me back to the start of my question. My closest friends are telling me the one thing I need now is to not date. They tell me if I can figure out how to be happy on my own. I'll have a better chance of finding happiness with someone else. The thing is, I am not totally convinced by this. I enjoy dating, but I also understand that what I'm doing

clearly is not working. So what in the world would you say to a guy like me? Are my friends right? Should I try to enter into a period of being single by choice? How could you? How could you could I actually benefit from being single if I ultimately really want a partner and family? And if it is helpful, what tips do you have to help me put this period of non-dating into practice and to make it stick? Thanks for your advice, Ronan. It's a great question. Yeah. And it's interesting coming from a 40-ish man. Yeah, I like it. Because men can marry when they choose to, just like you did. Well, yeah, I thought that was so interesting what you said. When you asked Craig that question, I thought, I think it's timing.

Yeah. That when a guy feels they're ready, then who's in front of you? Right. Just crazy. Mm-hmm. Yeah. Yeah. It's crazy.

It is crazy. And then it takes your second marriage to figure out. You need to be discerning. For some people, like, they don't. I know. I know. They never figure it out. I know.

It's just like fascinating. My technique for the second one, I thought was pretty good. I think that is really, I thought that was really helpful for other people to hear. The other thing I'm curious is, is that, cultural that men its timing? Or is it, I don't know, it's just nature or nurture? Yeah, yeah. I think a lot of it is cultural, right? We grow up waiting to be chosen, you know? At the school dance, you don't get to dance, or at least in our generation, you didn't get to dance if somebody didn't ask you to dance. Yeah, and then if you are the chooser, then men are like you're aggressive.

Oh my gosh, there wasn't any choosing, well, now for my generation. Yeah. I don't know my I don't even know my generation for me. Yeah. Can I give you just a little bit of a different thought process behind it? That's why you're here. Imagine as a 17-year-old and you're walking into a sock hop, which I just use for effect, but a dance, a party. But there are a lot of kids going, what is that? What are your socks to do with anything?

But we used to have these sock hops or it's a school dance. So imagine you're 17 years old and there's a bunch of girls in there and you go ask somebody to dance and they say no thank you. Oh, terrible. Yeah. Heartbreaking. And then you go to ask the next person and they say no, thank you. Oh, no, I don't like this. But that's how it was.

Yeah, that's hard. That's very hard. That's how it was. So the question you have to ask yourself as a guy is, do I just take what I have or do I take the chance to asking the next person and they say no? Yeah, the courage. That's real. It's real. It's an important perspective for sure.

Yes. And it is hard. But ultimately, you choose, right? It's scary, but, you know, so imagine the girl who is standing in the same sock hop with her shoes off now. I'll embarrass because she's standing in her socks. See what I have to put up with me. I have four siblings waiting to be asked

and people are just passing her by and they're a bunch of shy boys not even trying whereas a guy can decide the decision is still a man's to make. Is it though always? I just think culturally that is what we say yes.

I think culturally that's what I was saying. The original question was is it nature or nerdy? nurture, I think a lot of it is the culture that gives that power. I agree. To men. Now, it's a difficult power to have because with power comes responsibility and hurt and risk and all that. But, you know, even to this day, as you said, Tracy, if a woman crosses that dance floor to ask, she's aggressive. Oh, oh, oh, oh. It's an unattractive quality. So now I either wait to be to dance or I don't dance at all. I don't necessarily.

I'd necessarily agree with that. Okay. And I also would say, as a boy or a young man, if a woman walked across the floor and asked me to dance, it was no way I was going to say no. Well, I think, obviously, there's all different kinds of people. There's all different kinds. I mean, and, you know, then we're not even entering into the gender fluidity within this conversation. That is so much a part of what the younger generation is making sense of. And I think they're actually doing that really beautifully.

I do, too. And I've learned so much from the gender conversation and how it's expanded. I've learned so much about myself and what are the expectations that I didn't know were expectations about being a woman that I'm like, oh, I don't need to own that because I just thought that was a given. But now I know it's not, you know. But I think the societal norm, yes. I mean, I had a guy saying to me recently, yeah, you can't make a man do anything he doesn't want to do. But culturally, you can make a woman do a lot of things she doesn't want to do because we're trained. culturally to acquiesce in that way, that that's our role that we are. But I mean, this guy,

Ronan, I love the question because, first of all, what I'll say to Ronan is no one knows you better than you. That's right. And your friends can have all the suggestions in the world. And some of them might be helpful ones and some of them might be ones you want to consider. And then I think the thing that you have to do is ask yourself, does that feel right for me? Does that really feel like what's going to get the growth to happen? Yeah. And sometimes not dating helps people discover that. And sometimes dating is the thing that helps people discover that.

Well, and it's interesting when I think to your point, Craig, when you had your 32 list item, that was all about Kelly, right? I mean, and that's sometimes what we do. Forget you. I think that's what a lot of people do. It's like there's a list of things that I need in the other person. And some of them, a lot of them are superficial, like height and career and income and what school you went to, right? But it's all about the other person meeting a checklist.

What Ronan's friends are suggesting and what I agree on is like, okay, there's that list about the other person, but what's your list? What is your 32-point list about yourself that you need to explore? And I think a lot of men, and I hate to generalize like that, but, you know, so many women are self-reflective in our groups. We live in conversation. We live in a social world where we're constantly analyzing ourselves and each other in our conversations. This is the dialogue of women, and men aren't doing that as much. I think the younger generation. is doing it more. Yeah, I do see a lot more of it. I see a lot of it online and I really celebrate it. I think it's beautiful to see men have these deeper conversations about who they are and what they want. But the norm is no. And then the other thing to me is the invitation, right? It's like, yes, that's the cultural norm.

But the invitation is really to remind everyone men and women to take into account who they are. And what is important to you? You know, is somebody's height the most important thing to you? And why? Why? Is it because of what other people see or is it because of you? You know what I mean? Like, what is it? And I think those reflective questions not only help you in dating, they just help you in life. So let's help wrong. What are some of these questions he should be asking himself? Well, you know, just like in developing your life when I talk to young people, it's like, who do you want to be? What do you care about? And not what do you want to do, not what title you want to have, but how? How do you want to show up in the world? What's important to you? Is it kindness? Is it empathy?

Is it money? Is it money? Yeah, for some people, it is. For some people, it's security. Financial security. Some, it's emotional security. Is it important for honesty? For me, for example, like, I knew that, you know, you date enough people, you date people that just cheat, right?

And one thing I learned, luckily I learned it soon, I realized the cheating, if I was dating a cheater, that had nothing to do with me. You know, because I am not inherently a cheater or a liar. I mean, I would never, I would rather just look somebody in the face and say, we should break up because I'm thinking about dating somebody else. And I'm not going to hold you hostage while I go experience stuff. So I had to pick somebody who had the same values about that as I do, right? I didn't want to be married or date somebody that I have to worry about who are you texting, what's on your phone, where did you go? That trust is not an anchor.

And because it was important to them, not because it was important to me, that they were the same. That they had the same quality, you know, that was way more important to me than what career, you know, because I had dated people who were broken, in my opinion, broken in that way. And it's like, that's not fun to me, you know, guest. whether my partner is faithful. Like, some people are good with that game. Yes, some people that engages their chemistry. I don't know.

And I have no judgment, really. Like, there's things for people. Everybody has different values around those things and what's important. Some people don't want deep conversation. Yeah. Some people that is not their thing. It feels invasive. It feels uncomfortable.

Some people do, you know. I also think for Ronan, I have come. to really know that there's a big difference in somebody that I'm looking at dating as a partner and somebody that's somebody to enjoy and take what I like and leave the rest. And I learned as I've gotten older, like chemistry is not a relationship. Who say that again? Chemistry is not a relationship. And love does not always include chemistry.

Yes. And I'm somebody who wants both. Now, everybody's not like that. Some people are really don't want sort of the passionate chemistry of, you know, intimate physical energy. That's not their thing. And you don't want to be in a relationship with somebody who that's their, one of the ways they communicate love. You know, like, for example, I have male friends. I have one that we literally text and it's not flirting and it's all close.

And fashion and shopping. And it's like a version of a relationship. He's the sexiest little thing. He's young. There's never been anything physical. But we have this amazing like exchange that happens all the time. And I don't have that with my husband. No.

No. That sounds fun. But that's fun, right? It's like so fun and I'm single. Then I have a friend I go to the movies with. You know what I mean? And then there's people that so. Yeah.

And there's an, and obviously. if I end up in a relationship with someone, those probably will not continue, you know, those different things. But my friendships will continue because you also can't expect your partner to be everything. That's right. All right. So this is perfect. So, you know, how do we help Ronan become a better, a better subject for women? How do we help him make himself into a more attractive? Well, I think he sounds like he's attractive. He's having no problem dating. So what I'll say, But it's not sticking. Yeah, but that could be timing.

Right. That could be tight. That could be him. You know, that could be him just not choosing. He may not be ready to really settle down. The other big thing I'm going to say, look, I'm 52. I don't know. You know what I mean?

Well, this program is in my opinion. You don't have to know. We just have our deeply held opinions about Ronan's life. Exactly. But this is what I'm saying. I might not. meet a partner. Yeah.

Okay. I'm saying, like, I know there's this assumption, right? And the assumption is if you don't, there's something wrong with you. I don't agree. I agree with you, not agreeing with that. You know what I mean? Like, I'm just like, no, I don't, that's, no. I'm a great match and a great catch and all those things, but I also am going to wait

for the right person. So to Ronan, I would say, let yourself own the fact that you want a relationship. And you are going to do all the things you know how to do. to walk towards that. And if it doesn't, if you don't find the right person, it's not a reflection of you. If you're doing all the right things.

You know what I mean? I think that's the first thing I would say to Ronan. The second thing is ask yourself the question. Is dating helping you get towards what you want? Or is it actually distracting you because there's enough drama that you're not having the courage to say, this is what I want?

I had a friend who was dating recently, and the guy is out of a divorce, and there's just some stuff going on. And they really like each other, but he's kind of in a hallway. And she said, which I thought was the most courageous and beautiful thing, why don't you call me when you're out of the hallway? Yeah. You know? When you find a room. Yeah, when you find a room. And, like, if you still think I'm somebody that could be in that room with you, then give me a call.

I mean, I said to someone I was dating recently, like, I've come to realize that you are not a loving match for me. as much as I love you. And so I'm going to... That is a cold, nice, cold, bloody cut right there. See, I thought I'm all like, that's so true. Crazy like that is Mr. Nice guy. I didn't hear from him for a while. I bet.

He's still trying to figure that out. Yeah, well, he made his bed before when he wasn't showing up the way he should have. I gave him enough tries. And the crazy thing is for me, when it takes a lot for somebody to get inside my heart and feel safe. Once you get in there, it's so hard for me to get you out. And I have to really give myself time.

And that's the other thing I would say to Ronan about him sort of pining around this old relationship. Remember that in memory, you remember the good stuff. That's right. So it's not always the full picture. There's a reason that didn't work and you can trust that. And the right relationship, there's nothing you can do to make it stop. Like it will resurface itself if it's meant to be.

Well, that's the, I think that's, really great, solid advice. I think there are a lot of people who put too much pressure on trying to find everything in one person. I don't know if that's Ronan's issue. But if it is, I'd encourage him to, you know, be a little more open and to understand that relationships are long, and there are also ebbs and flows, right? So I think sometimes people who date don't realize that, you know, in long-term relationships, you're going to have deep, deep dips, and you're going to have a bad year. You're going to have a bad.

I tell people and folks think that this is harsh, it's like, you're going to have a bad decade. Yeah. You know, I mean, I've been married to my husband for 30 plus years. I mean, the truth is, if you add it all up, even the year, having, if the odds were, you're going to be married to your partner for 50 years, and 10 of those years could be bad, you know. That's. You'd sign up for it. You'd sign up for it.

You'd sign up for it. And that's really how it works out. That's the reality of it. The reality is that if you choose to have a traditional marriage and you have kids, let me tell you, the years of one to 13 will be bad for you as an adult, you know, because it's beautiful, but they'll take you for a loop and you love them and you don't want to hate them because they're cute. So you're going to be mad at them.

the person who is sitting next to you, the other adult. The one who helped you make it. The one who helped you make it. You know, so that's, that accounts for just a decade, right? I think people don't think about that as they date because they're trying to find the match that where all those 30 years are going to be blissful. Yeah, well, that's crazy. And it's like, that's just not going to happen. Can I just ask what some of the 32 things on the list were? Yes. Of the questions? I'm so curious. Is that okay? Is that a good? It's okay. It's okay. That is so good.

That is good. It is good. It might help Ronan. It might help Ronan. And me. Yeah, I'm trying to remember what they were. So what was item 30? So I guarantee you Kelly still has the list.

Oh, that's fantastic. You should get her on the phone. It was, it was significant. But she has this one thing that I didn't have on my list, but I would put on my list now. is are you comfortable with me being able to stand alone in a room? Do I say that again? Are you comfortable with me being able to stand alone in a room? So to your point, you have this full life and you have this aura about you that if we're going somewhere,

and the same with you, we go into a room, we might not be right next to each other. We're not going to be couple to couple. Are you okay with you? with me standing alone because I can stand alone. I was like, oh, okay. I love that question. So that was her question to you or you're a question to her? That was one of her questions to me.

That wasn't. That was the one that was not a category. I'm going to throw that at one of the people I'm dating right now. Yes. Look out, Mr. whoever you are. And I said, it's so important to me, especially the way my family is for you to be able to stand alone. So that's a great one. Yeah.

Yeah. And then there were sort of... That's a really good one. I love that question, actually. And then the one that we spent the most time on were, what are your deal breakers? What is it that you can absolutely not stand so I can make sure that none of them are like my favorite thing to do? Yeah, that's really smart. Yeah.

Yeah. And I will tell you, this was a... I just like the way you put it, though, because, you know, it's sort of innocently sweet and it's not so hard over the head. Like, can you stand? alone in a room. That's why I like the question, because I would ask that all wrong. Right. That's just the thing. I would ask that same question. Are you an insecure trifling ass? That is exactly right. Are you so insecure that you can't handle a strong? Are you uncomfortable with my bignness? Yeah. I would ask it all wrong. He would be surprised. Because I am a boss. I am a boss.

I'm a boss. Are you okay being in the belly? Can you level up? Can you level up? And then he's running away going on. I don't. It's like, he's aggressive. Yeah, that was really helpful. Yeah, that's a good way to think about it. And the one thing to bring it back to Ronan, is it actually better for Ronan to learn more about himself by not dating than dating a whole bunch of people? Because in the question, he's asking the question,

should I just not date? Well, I think it depends because I don't think we have enough information from Ronan, right? Like when he says distracting, what kind of distracting. So that's why I pose the question back to him of you have to ask yourself some questions to figure out, is that the right advice for you? Are you learning enough from dating that's actually giving you the right information about yourself? Or is the dating actually taking you off course? Because you're getting invested in the drama of things aren't working out or are working out. Tracy, I think that's a good point for everyone. Are people dating with intentionality

you know, to learn something, right? Or people just out there. And if you're not reflecting on why you pick somebody, you know, why the dinner went well, you know, why you laughed. And it's just happening to you without, you know, for men and women, for anybody of any sexual preference, it's like doing some self-assessment through the process, I would encourage, you know, because we're not taught to do that either in dating.

I agree. You know, there's no guide. Did he call again? Exactly. Yeah. You know, where did you go? Where did he take you? And are we asking.

Right. Are we asking questions of how do you feel? Why did you feel that way? Why did this relationship end? I think that may be what Ronan's friends are suggesting. And he can do that and he can do both. Yes, he can. He can date and can, but be more reflective about the process.

And I think that's true for us. everyone. If you want to have a partner, you've got to know yourself. It's dating and having an internal conversation about why your wise, your motivations, your history, your fears. What are you, you know, what are you mimicking, you know, like Craig? You were, you were imitating what you thought your mom and dad had. And you did that more than me. I was more like, I'm, I don't know if I want to be like them. You know, love them, love their marriage. But I didn't date for, I want to do what my mom and dad did.

And I think, Craig, you were more of that kind of, this is the way it works. It was a pattern or a strategy. The strategy is you go to college, you find a job, you have some single life, and then you get married. And I was just sort of checking off the, I was following a strategy. And that's just not, I don't want Ronan to do that. I don't want any, I want this generation of young people to be more thoughtful. Yeah. Thoughtful from an internal compass is my thing.

I always ask myself when I leave any situation, date included, how do I feel after? Do I feel, because sometimes you can think it's really nice in that moment and you leave and I was like, wait, why do I feel small? Why do I feel more insecure? Or do you feel good about yourself? Another question I do like to ask people is how do you argue? Oh, that's a good one, yeah. That was on the list. Yeah.

That was on the list. That was 12. Yeah, that was on the list. That's a good one. It's a good one. You know, because like my siblings, we all, there's a way that my family argues that I'm comfortable with. And I've been, because I get loud and then it's done. Like, I'm so straightforward.

I'm not somebody who's going to, like, hold it. Like, I'm going to say it. For some people, that's terrifying. Yes. Yes. terrifying and sort of sends them into another place. So those are, I just think, all those kinds of questions and asking them both of the other person and of yourself. Yeah. And it's not always a deal breaker. It's just something to be aware of because it will be a thing that you will need to

work on in the relationship. That's what makes relationship, marriage, partnership, so hard because you are taking two independent people with a whole different set of experiences and saying, you know, forever and ever, amen. Marriage is hard. Yeah. And it is reasonably hard, you know? It's the right kind of hard. It's the right kind of hard, but don't get upset when it's hard, you know?

Well, I mean, you know, social media has made a myth of so many things because life requires you to show up. That's right. And if you want anything out of it, it's going to be work. Yeah. You know, and relationships included. Someone told me this great just metaphor of imagine that the people you're closest to, you're going to step on each other's toes.

And so how do you work out the stepping on toes? Do you just blame them? That's right. Or do you figure out how to not step on each other's toes? Or is that just the nature of what a relationship brings? And then how do you work those things through and work those things out? And it's important for Ronan to understand that it's work. Yeah.

Because sometimes, maybe for men or if they can be choosers or people in general, they think something, there's something wrong in the dating process. And it's like, nah, it's just, you know, what it means to be with somebody else. Yeah. It's complicated. It's hard. It requires compromise. It requires you to change and adapt all throughout the process. You know, you can't just come in and say, well, this is who I am, you know, and this is, these are my habits. So some of the list is important, but when you couple, you will not be able to find the exact right person who just balances you on all those 32 points. Exactly. It's just, you know, then you will be alone and that's okay too. Or you're going to try and date yourself, which you don't want to do.

And that won't be fun because you'll find out all the worst parts of yourself and you will be divorced from yourself. Do you have this, you as the man in your relationship, as since we've been talking about it from our perspective, do you feel that you have continued to grow in your current marriage and that it asks that of you? Absolutely. Because it sounds like the list was my list, but the discussion that it brought continues to happen to this day. That's what's so beautiful about it because I can tell the growth comes because when we go to dinner on our date nights, we're talking as if we had just met. Like, we are always talking.

And so I've just gotten better at being in a relationship. And that's what I... That's a really nice thing to say. Like, I've gotten better at being in a relationship. That's why, in our opinion, in my opinion, the show is like, let's teach everybody how to get better at this. Or to know that it's something, it's an important muscle to build. Perfect time to give Ronan some takeaways.

Okay. Okay. And I'm going to... You took notes. You take away. Come on, Coach. Do it. Yeah. Tell us. The self-reflection has to be at the top. Self-reflection has to be at the top. And Tracy, you said something that was really interesting. Do you even want to have a connection with... Chemistry, chemistry and love, yeah. Chemistry and love, or is this just a... I'm not in love with you kind of thing. What's important to him in a relationship?

What's important to him. And then the third thing that I had, and Mish, you said this, is you have to do the extra work. And not only being in the relationship, but trying to find a relationship. And can I reframe that? Yes, you can reframe that. So let's just call it the work, because it's not extra work. That's just the work it takes. Okay.

Yeah. Do the work. Do the work. And I have one last thing. It's, and there's not. no one right way to live a life. I mean, maybe, Ronan, you don't choose a life partner. Or it doesn't happen or you don't find it.

There's so many ways to be happy and it doesn't just look like marriage, two kids, and a house. There's so many examples of people who live full, wonderful lives that aren't following the quote-unquote traditional path. And I just want Ronan not to force something that isn't there. Yeah. It's like stars aligning. It may not happen. So now the work is how are you happy with the life that's right before you?

That's what I want for my daughters. That's what I'm raising them to be is like, how are you happy with how like is working out right at this moment so that you're not living in regret or living in, I wish or holding up your life, you know, So when you're waiting for it to happen, you know, in the meantime, Ronan, live. Yeah. Live, grow. Adapt for your own self. Yeah. And if there are those things that you are like longing to do with a partner, are there versions of that you can do with yourself?

Which is the thing that I have really discovered in my life. I'm like, all right, so how can I do that on my own while still dating? Well, Tracy. What a fun conversation. I love you. I love you right back. Yeah. This is so nice. So nice. Thank you for doing this. Yeah. Yeah. And, you know, your vulnerability, your willingness to share, be open. Always refreshing. Thanks. So see you. That's my currency. That's what you get. You do it. You use it well. Thanks so much. I'm back soon. I will.