In short
Podcast Episode Notes: IMO with Michelle Obama and Craig Robinson
Episode Title
Dating Should Be about Pursuing Joy with Tracee Ellis Ross
Episode Overview In this episode, Michelle Obama and her brother Craig Robinson are joined by actress and entrepreneur Tracee Ellis Ross. They tackle a listener's question about dating, focusing on the experiences of a man who has struggled in love but desires a partner and family. Tracee shares her insights on singlehood, dating readiness, and her personal dating checklist, while Craig provides a male perspective on dating dynamics.
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Key Themes and Discussions
- Embracing Singlehood
- Tracee discusses the importance of enjoying one's own company and embracing being single.
- Highlights the concept of being ready to date and how life experiences contribute to that readiness.
- Dating Perspectives
- Craig offers insights into what men often look for in dating.
- The trio discusses the generational shifts in dating expectations and experiences.
- Tracee emphasizes that it's crucial to date with intention and self-awareness.
- Listener Question: Ronan's Dilemma
- Ronan, a 41-year-old man, seeks advice on whether to take a break from dating after experiencing frustrating relationships.
- His friends suggest that he focus on being happy alone to improve his chances of finding a partner.
- Self-Reflection and Personal Growth
- The importance of self-reflection in dating: understanding one's values, needs, and what one wants in a partner.
- Discussion on how to approach self-discovery while dating or choosing to remain single.
- Cultural Commentary on Dating
- Insights into the cultural norms that affect dating dynamics, particularly around masculinity and expectations.
- Discussion about the impact of societal changes and gender roles on modern dating.
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Takeaways for Ronan
- Prioritize Self-Reflection:
- Identify what you want in a relationship and consider your own values and needs.
- Define Your Dating Goals:
- Determine if dating is helping you move toward your goals of partnership and family or if it is distracting you from self-discovery.
- Engage in the Work:
- Understand that relationships require effort and commitment. Being single can also be a time for personal growth.
- Challenge Cultural Norms:
- Recognize societal pressures and expectations surrounding relationships and define your own path.
- Embrace All Life Possibilities:
- Understand that a fulfilling life can exist outside of traditional relationship structures. Focus on living fully in the present.
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Final Thoughts
- The episode closes with a reminder that navigating relationships is complex and involves ongoing self-improvement and adaptability.
- Michelle, Craig, and Tracee emphasize the importance of pursuing joy in dating and within oneself, framing life as an adventure full of possibilities.
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Featured Guest
- Tracee Ellis Ross: An actress, director, producer, and entrepreneur, known for her work in both television and film.
For more engaging discussions and advice, visit [IMO Podcast](http://imopod.com).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00You 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 one to get the trait? I would ask it all wrong. He would be smart from the start. Because I am a boss. I am a boss. I'm a boss. Are you okay being the belly? Can you level up? Can you level up? And then he's running away going, she's aggressive.
0:47How you doing? I'm doing great. Yeah, feeling good. Another day. Alive. We're getting to that age where, you know. No, we're not. I'm just blessed. Woken up. And you don't think we're at that age? You're older than me. Well, we are. Yeah. We were in our 60s, my friend. I know, but I'm hoping I got a 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 did. You know, the girls came over for dinner, and I was so tired that I left them at the table, which is unusual.
1:30because 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, but yeah, 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?
2:09How 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. So I'm learning a lot about the Airbnb life since we don't do that. You don't get to do it. But the girls do. Yeah. And Sasha, whenever they're traveling. And so our kids, Avery and Leslie and Emily and Elena, they all there. They have no qualms. Let's go. Let's find a place. It's really a different intergenerational use.
2:45I 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 girls trip, a friend gathering session.
3:27But anyway, well, I'm glad you are comfortable in your Airbnb, mister. So you'll never stay with me ever again, I guess. No, I would not do that. Have we been displaced? You have not been displaced. Oh, good. 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? 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 mini pools in your house. Yes. Yes. Well, what are we talking about today?
4:08So 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 until I got to college. With you and these sports, it's like spending too much time in the gym.
4:59Yeah, yeah. It really was too much time in the gym and focused on my schoolwork. 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?
5:45You know, are they, first of all, are they good at basketball? So I generally only dated the people that you said were actually good. Right. You know, also 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. Mm-hmm. 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.
6:30So Mish 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'm thinking to myself, it's going to last about a month like most of your relationships did. That's not true. 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 want to call my boyfriends 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 Brock. And she gets out of the car. And I remember mom's first thing was, oh, at least he's tall.
7:08That was her first thing she said. Because Misha 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 to 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 him?
7:52This 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, ooh, want to go to movies or something. It was like crickets. Yeah, but you're just an all around nice guy. You weren't shy, but you definitely weren't, you didn't have some lines.
8:44And 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, I 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, forget high school, college, because you're just doing what you're doing then. How do you think your friends think about selecting, dating?
9:27Here'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 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.
10:20We 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 started dating, 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 was like, you have your own bedroom. I have my own bedroom. If it doesn't work, we just say, c 'est 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.
11:0332 things that I had individually that I wanted to discuss. 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 things. I think that would have been a reasonable thing to think. I was burned. That's how men are. 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.
11:42She knew everything about me. And so it worked out. Thank goodness. But let's bring out our - 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 just really, she got manners. She's just so sweet. She's got manners. She was raised right. She's funny talking about being funny. Now, 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 Patter? I guess not.
12:21You're bold. Okay. I'm sorry. I forgot. Oh, man. You let me do my job here. I'm sorry. I'm sorry. I interrupted. And so, without any further ado, Tracy Ellis Ross. Tracy! How are you? I'm so good. Like I said, family. I do feel like family. We got family in the house.
12:46Really interesting conversation. Oh. And I took some notes. Oh. 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 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. I'm still single, so noted now. You know, there's still time. The guy out there breaking his hip trying to play basketball.
13:23Yeah, 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 when 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. 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, renegades coming back. There's been an accident, you know, and I'm like, ugh, because I'm always like, be careful playing basketball.
14:02You 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 gauze thing on his lip. Oh, my God. 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 you're 10. And now your lip is split. So we digress. That's okay.
14:38No longer can we, are we dating people? No, but I am. I was about to say, I was like, Tracy, Tracy's, you know, my girl. Yeah. The tales from the road. And I do bring stories home. She's got stories. I'm like, 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 more open. 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. More open than it should. Yes. Yes. Okay. All right. More open than it should be. But I do date.
15:17And it's a fascinating adventure out there. 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. Yes, you are. 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 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.
15:59Yeah, 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.
16:50And 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. And I don't know whether the whole movement is about sort of re-harnessing us, you know? Is it really about 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, right? I mean, mostly they are, you know, 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.
17:39You 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, but I think 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.
18:17Oh my God, we had a great dinner. 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, the power of reach. This is what I'm saying, tales from Tracy's. It's fun. It's really fun to share. Tracy tail. But one of the reasons though, because I had to ask myself that question. I was like, what is this about? 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 full, very whole person who knows myself, who is in charge of my life, and who lives a very full, just robust life.
18:59So 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 did enough of it where I was controlled and felt like I was a possession or whatever those things were, or prize. And I have no interest in it and I will not do it again. I'm sorry.
19:40No, 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 the guys you're meeting? That's obviously, it's a generalization. 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. That there's times where 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?
20:15Yeah, like, I'm so sorry. And your bedpan. 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 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. 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, but that's just not something I'm comfortable with.
20:51So 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, you know, 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. I've had some doozies. Yeah. But it's just, I just love watching your life because you were modeling so many things, the next phase, how many versions of ourselves we can become at all ages in life, you know, and how to build the life you want.
21:35Yes. 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 girls. 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.
22:15And, you know, have you thought about the amount of money? Your 32 list items of who you want to marry or are you more busy planning, picking out your photographer? Yeah, it's interesting that whole, I hope that that is starting to dissipate culturally. I hope so. I really do. I think social media is perpetuating some of those things in a really big way. But 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 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.
23:00That'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.
23:40And it's built a really beautiful experience around me. And I have incredible friends. Well, this is a good segue to get to our question. Let's do it. Especially the talking about dating and meeting people. And we have a great question. So Natalie, our producer, is going to be the question for... 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.
24:19Throughout 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've 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.
25:01We 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.
25:46The 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 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.
26:29Because 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? They just pick. Right. Which is crazy. Yeah. It's crazy. It's so crazy. It is crazy. And then it takes your second marriage to figure out you need to be discerning. And for some people, they don't. I know. They never figure it out. 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.
27:01The other thing I'm curious is, is that cultural that men, it's timing? Or is it, I don't know, it's 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. I don't even know my generation, for me. Yeah, yeah. Can I give you just a little bit of a different thought process behind it?
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27:42That'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 there are a lot of kids going what what is that what what are your socks have to do with anything uh you go 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. 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.
28:20That'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 of asking the next person and they say no? Yeah, the courage. Yeah. That's real. That'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, all embarrassed because she's standing in her socks.
29:00See what I have to put up with. 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 nurture? I think a lot of it is the culture that gives that power to men. Now, it's a difficult power to have. because with power comes responsibility and hurt and risk and all that. But even to this day, as you said, Tracy, if a woman crosses that dance floor to ask, she's aggressive.
29:52Oh, oh, oh, oh. It's an unattractive quality. So now I either wait to dance or I don't dance at all. I don't necessarily agree with that. And I also would say, as a boy or a young man, And 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.
30:30I 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 say 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.
31:07But 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? And sometimes not dating helps people discover that. And sometimes dating is the thing that helps people discover that. And it's interesting when I think to your point, Craig, when you had your 32 list item, that was all about Kelly, right?
31:50I 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 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 so many women are self-reflective in our groups.
32:42We 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.
33:23You know, is somebody's height the most important thing to you? And 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 Ron. 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 you want to do, not what title you want to have, but how do you want to show up in the world? What's important to you?
34:00Is 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 that cheating, if I was dating a cheater, that had nothing to do with me, you know, because like 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.
34:51So 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 you texting, what's on your phone, where did you go? That trust is not an anchor. That trust is not there. And because it was important to them, not because it was important to me. But they were the same. That they had the same quality, you know? That was way more important to me than what career, what, 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, guessing whether my partner is faithful.
35:29Like, 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, 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 am looking at dating as a partner and somebody that's somebody to enjoy and take what I like and leave the rest.
36:08And I learned as I've gotten older, like chemistry is not a relationship. Ooh, say that again. Chemistry is not a relationship. Yes. And love does not always include chemistry. Yes. And I'm somebody who wants both. Now, everybody's not like that. Some people really don't want sort of the passionate chemistry of intimate physical energy. That's not their thing. And you don't want to be in a relationship with somebody who that's 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 clothes and fashion and shopping.
36:56And 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, 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.
37:35That's right. All right. So this is perfect. So, you know, how do we help Ronan become 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 problems dating. So what I'll say— But it's not sticking. Yeah, but that could be timing. That could be timing. 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, it's in my opinion. You don't have to know.
38:15We 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 am 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.
38:56And 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?
39:38Yeah. 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. Yeah. As much as I love you. Yeah. And so I'm going to— That is a nice, cold-blooded cut right there. See, I'm all like, that's so true. Crazy like that. It's 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.
40:17I 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.
40:48Well, 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 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 in long-term relationships, you're gonna have deep, deep dips and you're gonna have - You're gonna have a bad year. You're gonna have a bad - I tell people and folks think that this is harsh. It's like, you're going to have a bad decade.
41:29Yeah. 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, 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? You'd sign up for it. You'd sign up for it. You'd sign up for it. You know? And that's really how it works out. That's the reality of it. But the reality is, is that if you choose to have a traditional marriage and you have kids, let me tell you, the years of 1 to 13 will be bad for you as an adult, you know, because it's beautiful, but they'll— Yeah.
42:10They'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 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 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?
42:42Yes, you can. Yes, you can. Is that valid? It's okay. Is that valid question? You're okay to answer that? That is so good. It is good. That's a great question. It might help Ronan. It might help Roni. And me. Yeah, I'm trying to remember what they were. What was item 30? So I guarantee you Kelly still has the list. Oh, that's fantastic. We should get her on the phone. 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?
43:28So 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. We're not going to be couple to couple. Are you okay 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 your question to her? That was one of her questions to me. That's a great question. 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.
44:03Yes. Look out, Mr. Whoever you are. Can you stand alone? That's a good question. 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. 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 it's sort of innocently sweet and it's not so hard over the head.
44:43Can 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 one to get the trait? I would ask it all wrong. He would be so awesome. Because I am a boss. 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, I don't know. She's aggressive. Yeah, that was really helpful. Yeah, 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?
45:32Because 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 posed 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.
46:06Tracy, 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 picked somebody, you know, why the dinner went well, you know, why you laughed, and it is 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— Did he call again? Exactly. Yeah. You know, where did you go?
46:47Where did he take you? And are we asking— What does he do? 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 everyone. Yeah. If you want to have a partner, you've got to know yourself. It's dating and having an internal conversation about why you're wise, your motivations, your history, your fears. What are you mimicking? Like, Craig, you were imitating what you thought your mom and dad had.
47:33And you did that more than me. I was more like, I don't know if I want to be like them. You know, loved them, loved 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 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— Or an expectation to do that. I don't want any—I want this generation of young people to be more thoughtful.
48:18Yeah. And 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. That was on the list. That was 12. Yeah, that was on the list. That's a good one. That'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.
48:58And 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. 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.
49:43Marriage is hard. Yeah, it's, 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, that's right. And if you want anything out of it, it's going to be work, 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?
50:20That'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 there's something wrong in the dating process. And it's like, nah, it's just what it means to be with somebody else. It's complicated. It's hard. It requires compromise. It requires you to change and adapt all throughout the process. You can't just come in and say, well, this is who I am.
51:02And 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. 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 as the man in your relationship, 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?
51:42Absolutely. 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 it's, and so I've just gotten better at being in a relationship. And, and, 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, we're in, in my opinion, the show is like, let's teach everybody how to get better at this.
52:25Or 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're the master takeaway. You took notes. You take away. You're the only one to do it. Tell us. The self-reflection has to be at the top. Yes. 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 and love, yeah. Chemistry and love, or is this just the, I'm not in love with you kind of thing? What's important to him in a relationship? What's important to him.
53:04And 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. Let's just call it the work. Because it's not extra work. That's just the work it takes. Okay. Do the work. Do the work. And I have one last thing. And there's 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.
53:52There'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. 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. Yeah. 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? And waiting. Waiting for it to happen, you know?
54:34In the meantime, Ronan, live. Yeah. Live, grow, adapt for your own self. 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 was so nice. This was 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 ya 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
From the publisher
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.
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