The #1 Mistake You Can Make On A First Date

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1:37Hey everyone, welcome back to Jillian on Love. Today I answer two questions that are really important and really juicy. We've got one person, she's 33, she lives in New York City, and she keeps going on these dates and not getting a second date. And she's trying to figure out what is actually happening. And then we have someone else. He's in love with his girlfriend, but he's realized that he has disorganized attachment. He completely shuts down and abandons his girlfriend when there is conflict and they are now no contact. and he is realizing that he really wants to fix this. So can't wait to hear what you have to say about this.

2:22I think this is going to be incredibly helpful. So here I go. Hi, Jillian. I'm a 33-year-old woman in New York City. After taking a break from dating over the winter, I've gotten back on the dating apps and have been pretty consistently dating. thing, what's confusing me is that I can get dates. I have enjoyable first dates and I generally have no trouble like building the conversation and the connection. Many of these dates involve, you know, shared interests, some laughter and enough compatibility that I would absolutely be interested in seeing the person again. The problem is, is that I cannot seem to get second dates.

3:10This has happened enough times that I know I need to examine my own role, like what may be going on, but I'm struggling to identify what exactly is happening. I've asked friends, family, male friends for feedback. One theory that's come up is that I might be approaching first dates too much from a getting to know you perspective and not enough from a creating chemistry or this tension perspective. In other words, the dates are thoughtful and engaging and have a lot of substance, but perhaps not romantic enough. Side note, a lot of the guys that I've gone on dates with have suggested things like walking in Prospect Park.

3:58So maybe not the most romantic of settings, but a good way to get to know someone and have a low stakes chat. So the challenge is that I genuinely don't experience attraction the way that many people seem to describe it. I rarely know after one date, whether I'm interested romantically or sexually, attraction often develops through getting to know someone over time. And I don't think there's anything wrong with that. So my threshold for a second date is usually, did I enjoy them? was their compatibility am I curious to learn more and it seems like many of the men I'm meeting are using a very different threshold but this is just a theory so my question is how do I know whether I'm genuinely missing a skill around creating romantic connection versus simply running into a dating culture that expects immediate chemistry and if attraction tends to grow over time?

4:55How do I date effectively without feeling like I need to like manufacture this flirtation or this sexual attention with someone I barely know? I love your perspective. I'm feeling super stuck wanting to be open to feedback and also not wanting to assume that every disappointing dating outcome is something I'm doing wrong. This is such a good question. I had to really think about it actually um no I don't think it's anything that that you're doing wrong um I appreciate that you know you want to look at your own role and that you're asking friends for feedback um and there's no doubt that that the dating culture today is sort of um And no, it's just shallow.

5:42People are just looking for that instant spark or they write people off too soon. So here's here's a few thoughts that I have. And by the way, you are correct. There is nothing wrong with the fact that it takes you longer than just one date, which it sounds like your dates are not even that long because they're a walk, which I'm going to get to that in a moment. there's nothing wrong with you that it's a slower burn for you. And also for a lot of people, especially men, it's sort of, it's not a slow burn typically for men. Typically men know if there's a chemistry or if there's something that they're attracted to physically and that's sort of like what they're looking for right away.

6:37And the fact that you are looking for other types of chemistry like compatibility or shared interest, which is its own type of chemistry, before you are able to assess if there's physical chemistry is completely normal. I think it's for a lot of women. It is not typically how men operate. I think men operate more from, is there something physical there? And then they look for the other stuff. So there's that. But, and that's something that, you know, you are working with, right? But here's something that you said that I completely, that I picked up on from what you said that I agree with. I love taking a walk with a friend, with a loved one, with a partner.

7:29I think walking is an amazing co-regulation skill. I think it's a lovely thing to do with someone. And I might get pushback for this, but I don't think it's an appropriate first date. And the reason why is because I think it's actually in its own weird way too intimate for a first date. Like a walk with someone is, it's like you almost have to already have a comfort level with them to enjoy a walk with them, to experience that ease. Because when you're walking, you're walking side by side. You're not facing each other. You're not able to, you know, you can't be walking and looking at each other the whole time.

8:18You are maybe sometimes turning, looking at the person, looking ahead. And that is something that you do when you're already at ease with a person. It's not something that you do where you can get to know someone. And it's certainly, to your point, not an environment that is conducive for creating any sort of flirtation or chemistry. Sorry, it's just not. And I mean, it would even be better if you met somewhere like at a cafe, if it was a day date, to meet at a cafe where you're sitting down and facing each other and having a conversation. conversation and then maybe if you're having a good time afterwards you go for a walk or afterwards you go to a museum since you're in New York City or afterwards you know you check out a movie but it's not it's not a good idea like everyone who's dating like don't make the first time you meet someone to go for a walk and I and I think that part of the reason why people are doing that is because we're trying to make it, people are trying to make it so low stakes because it's like, oh, I don't wanna waste my time.

9:33And look, I understand if it's a first date and you have never met this person ever, except for like, let's say on a dating app, maybe you don't wanna commit to the dinner. Maybe you don't wanna sit across from someone for a whole dinner because it's like, what if you don't even like the person? I get that. But then my point would be then, and I am, those of you who follow my work know that I'm staunchly against spending days and days and days, and some of you are spending weeks texting back and forth. I think that's ridiculous. But what I don't think is ridiculous is having at least a couple of conversations or a FaceTime or something like that, where you build some sort of rapport that's beyond text messages.

10:24If you are wanting to meet someone with whom you could potentially spend your life, you got to put in a little bit more effort than just a walk and a little bit more, um, yeah, just a little bit more investment than just a walk. And again, if it's, you know, if let's just say it's not that clear cut who pays, who doesn't, someone should be like, I'd like to meet you, whoever the person that is, that's initiating just something. I just, I agree I think it's impossible to build to see if there's chemistry from a walk and I think that everyone needs to be putting their be willing to put their get their feet a little bit wetter and to invest just a little bit more and if you are nervous then have a FaceTime call with this person first to see if there is rapport and you like the way the person looks and you think that they are attractive enough and then make it just have a little bit more effort.

11:34If you want it to be a day date and you want it to be kind of low stakes, at least you're sitting down. You are, there's like, you're sharing, you're, you're sipping some coffee together. You're eating a meal together and you're having a conversation where you are watching each other's body language. Like right now, like I use my hands a lot and you're seeing that we are, we are creatures above anything else. And we need in order to know if there is chemistry with someone, we are communicating with our bodies. We are communicating with our facial expression. It's not just what we say. And so much of that is lost in a walk.

12:20That's what I want to say. That's like the most important thing that I have to say. And as for your questions about flirtation and chemistry, well, you know, I don't know if this is you, but I think this is something for you to think about and certainly something for people who are listening to think about if you're running into this problem. Sharing a meal together, doing an activity together that's not walking. Maybe it's like, I don't know, again, like playing something like miniature golf, something that's going to have some energy behind it. There's no energy behind a walk. Beautiful, peaceful, bonding, co-regulation activity to do with a friend or a loved one or a partner, that includes a partner, does not have enough energy or aliveness when you're just meeting someone.

13:17And so it falls flat. So my, so when you do go on a date, that's not a walk. Are you laughing? You know, like, are you, um, are you open? Are you in your head? Are you feeling closed off? You're like, I don't know if I like this person. So I'm kind of leaning back. Are you sharing about yourself? Are you not just asking questions about them, but are you sharing something about you? which again is vulnerability. These are the things that create connection and connection is what we're actually looking for. Can't really feel a physical chemistry. Like, yes, you can find someone handsome. You can find someone beautiful and that could pull you in, but that's actually lots of people find lots of people attractive, but they don't feel that connection with them.

14:09And so then there's no chemistry. Things for you to think about are, am I open? Am I in my head? Is my body language tense? Am I too much in interview mode? Am I not sharing enough of myself? Am I not allowing myself to be animated? You know, am I kind of falling flat in my body language? So that's what I have to say about that. And I hope it helps. So what I would say is if someone is suggesting a walk, I would say, you know, I really prefer, you know, we've we've talked on the phone. We've been texting back and forth. I would love a conversation where we can sit down and face one another. And if there if he's not then saying, OK, great.

14:58Meet me here. Don't meet him. Don't meet him. Sorry, just don't meet him. That's just a sign that he is just way too low stakes, way too passive in wanting to get to know you. And honestly, not mature enough. Come on, we have to be willing to sit down across from someone and to see if we have a connection with them. Want to be the one who's always in the know about the game, the scores, the plays? Here's a tip, the Apple Sports app. Just pick your favorite teams and get automatic live updates without even knowing their schedules. And when your team scores, it shows up right on your iPhone lock screen, making it easy to check in anytime.

15:38So rule the group chat and download Apple Sports for free on the App Store or find it on your new iPhone. Is your home wish list just sitting in your cart? Well, get ready to hit checkout because Wayday at Wayfair starts October 24th with up to 80 % off everything home. That new sofa, the rug you've been eyeing, the upgrades you've been putting off, they could all be way less during Wayday. It's Wayfair's biggest sale of the year, so make your list and mark your calendar. Shop Wayday starting October 24th for up to 80 % off everything home at Wayfair.com. Wayfair, every style, every home. Hi, Jillian.

16:17I am reaching out because seven months ago, I ended a relationship that has been the most meaningful relationship I've ever been in. And I ended it because of what I've now discovered through a lot of healing and work and digging is through a disorganized attachment that led to a lot of avoidancy and is kind of brought on by childhood trauma that I had not addressed and was really not aware of how influential it was in my life. I'm working really hard to understand how it is I got here to kind of re-script how I handle conflict in the future, which was a major issue. it's been a major issue in every relationship is anytime there's conflict I feel deeply unsafe and I retreat or I numb out and um you know I basically abandoned my partner in the moment I don't want that anymore I can see the pattern and I am working towards resolution I guess what I'm asking is, is it ill-advised to reach out to my partner after an extended period of no contact?

17:47She asked for no contact due to how I was responding earlier in this breakup of kind of a mania of just trying to prove to her that I'm changing and fixing things. And obviously I was kind of the furthest from the actual truth. Now as time's gone and emotions have settled and I'm really finding clarity in ways, but my love for her is still so strong that life is short. And I don't want to regret not at least giving her the best attempt I can because she got kind of the worst of me in a lot of our relationship. I understand that she is her own person and this may be deeply triggering to try and reenter anything.

18:39So I just wanted some advice to know if reaching out again down the road is ill-advised. Obviously, taking it slow. Hopefully, if I could just regain her trust and go from there is the goal. um well first of all i just want to honor the fact that you have um a lot of insight into what you're going through or what your problems are in a relationship and it sounds like you're really putting in the work to get to the bottom of it you you that moment where you said i don't want to i don't want to be like this anymore i don't want to this is not what i want to do anymore That part of you that draws the line in the sand has to be much stronger than the part of you that's afraid.

19:35So you have to have a compelling reason, even beyond your current, I don't know, girlfriend or ex-girlfriend with whom you're taking a break. You have to want this for yourself. you have to whether things work out with her or you get into another relationship you have to really decide that and i think you have but i really i want to drive this home you have to really decide that um that those days of you uh completely abandoning your partner during conflict are over. And you, it is actually a decision. It's a decision. We think that, um, that our behavior is out of our control and 99 % of the time it's not.

20:26And so, um, this is a hundred percent in your control. You know, some people, they shut down in conflict. I've, I've, you know, I've worked with many men who have had a very similar reaction to conflict and they grew up with violent fathers or violence between their mother and their father. I don't know if that's you, but it's important for you to understand and for everyone to understand that oftentimes our reaction to conflict is based on something that we learned, that we saw, that we witnessed, that was modeled to us in childhood. And so that feeling of being unsafe inside your bodies, you're having a very visceral somatic of the body reaction to to conflict.

21:22You know, it's like it's it's when we feel unsafe, we go into fight, flight or freeze. And so based on what you shared, it sounds to me like you are maybe freezing and then fleeing. Right. Because and then the person. your partner then feels abandoned because you've left the room literally and energetically. So how do we, how do we stay in the room? So another thing that could be going on for you, that's important for you to recognize and acknowledge and become aware of is it's possible that when you are in some sort of argument with your girlfriend and you start to shut down and pull away, that some of what is going on in your head, some of the narrative, the storytelling, the thoughts that are going on in your head is, I can never make her happy.

22:19I'm a failure. I don't know how to make her happy. Something I'm unworthy because she's unhappy, whatever it is. So you always, we can't really get to the bottom of this and heal by only looking at childhood. We also have to look at the story that we tell ourselves. We have to observe the story that we tell ourselves in that moment. And oftentimes it's happening so quickly, it's not conscious. But now as you bring it into conscious awareness, you have to recognize, okay, in that moment, the meaning that I am giving this conflict, the meaning that I am assigning to my girlfriend being upset with me is that I am a failure.

23:09And that kind of shame, sometimes referred to as toxic shame, is really prevalent with men in particular and very prevalent with those who have a lot of avoidance in their relationships. It's very prevalent in addicts, drug and alcoholics, drug addicts and alcoholics. And so that shame is very real and very painful. The problem, though, is that in those moments, and this is hard to say and it's hard to hear, but it's important, it's going to liberate you, is that you're making it all about you. It's all about you and your wounds and your trauma. And when we are in a relationship and we're making it all about us and our wounds and our trauma, we become too self-focused.

24:14And we become, without even trying to be, the narcissistic tendencies start to come up. Because in a relationship, we have to be cognizant of and care about how our behavior is impacting our partner. And regardless of what we did or did not go through in childhood. Want to be the one who's always in the know about the game, the scores, the plays? Here's a tip. The Apple Sports app. Just pick your favorite teams and get automatic live updates without even knowing their schedules. And when your team scores, it shows up right on your iPhone lock screen, making it easy to check in anytime. So rule the group chat and download Apple Sports for free on the App Store or find it on your new iPhone.

25:00Fall never arrives all at once. First the air, then the light. And slowly the things you love begin to find each other. A jacket meets a dress. A hoodie slips beneath a blazer. An old cap finds a new scarf. Because you don't simply step into the season. You create it layer by layer until it finally feels like fall. Find fall your way at Ross.

25:28And so when we get into that shame, Like I know like when if I get into my own little shame spiral, my own sort of self-deprecating shame, shame spiral, which I really don't do nearly as much as I used to gotten so much better at that. But I but part of the reason why I'm much better at not getting myself into that emotional state is because I understand that when I get into it, it's one thing to feel it. it's another thing to dwell on it. And that if I'm dwelling in that state, then I know that I am, that I am too focused on myself. I'm too focused on myself that I've like lost sight of like, what's really going on to make it work in a relationship.

26:11It can't be all about you and your discomfort. Like it, all of it is uncomfortable, you know, when it comes to a conflict, you know, a lot of experts will say that conflict is a part of relationship. And I would say that arguing is a part of a relationship. And it's definitely not a bad part because I'm sorry, but like to always agree with your partner, like all the time is a little boring because you're not supposed to be the same person. Once in a while, we need a little bit of the friction to remind us like, hey, I'm dealing with an autonomous person with their own mind. And by the, and I'm an autonomous, autonomous person with my own mind.

26:58And it's the fact that they have their own mind that doesn't always agree with me is literally the reason why I was part of the reason why I was attracted to them in the first place, because we don't tend to be attracted to people who are exactly like us. We may befriend them, but we don't feel attraction. So arguing is, we don't want to be constantly arguing, but having some of that friction is a natural part of a relationship and it's healthy. However, arguing is not the same thing as conflict. And what we want to be able to do is have healthy arguments or have an argument once in a while without it turning into a substantial conflict in the relationship.

27:43And the only way to prevent it from becoming a substantial conflict, because what's happening right now between you and your girlfriend or your ex-girlfriend or you and all the women who you've dated because you say that this is a pattern, is that the arguing has become a substantial conflict. The conflict is you shut down, you flee, and you abandon your partner when there is an argument. When really it's about let's face whatever is just like, you know, I've made you unhappy, right? Like that's an argument. It's like an argument is either you're not agreeing on the outcome of something that you want to have happen or one or both of you is unhappy.

28:32Not existentially unhappy, but just in the moment your feelings are hurt. Feelings are hurt. And so getting better at saying, you know, I'm sorry I hurt your feelings. Getting better at saying to our partner, I know you did not mean to hurt my feelings. I know you didn't mean this. I know that you meant something better. But still, it hurt my feelings. And our partner being able to say, I'm sorry I hurt your feelings. Yeah, I hurt your feelings. Not I'm sorry you feel that way. Not I'm sorry your feelings are hurt. which is just the worst douchiest thing to say to your partner, but just like, I'm sorry I hurt your feelings.

29:14And as couples, just getting better at that, despite the fact that you have a bad habit of abandoning your partner during tension, I have no doubt that there have been times where your partner could have approached it better because more times than not, it takes two to tango. Unless we're dealing with something straight up abusive, you know, and straight up toxic and dysfunctional. You know, I'm sure if your girlfriend was sitting here today and I was talking to her, there would be things that I could coach her on to make things better. So I don't want you to take all the responsibility and I don't want you to further hate on yourself because it's the hating on yourself that has led to this predicament to begin with.

30:02When you are feeling that fear, because here's the thing, you could do all the personal development work therapy in the world. It is not going to take away the fear. What's going to minimize the fear is practice. You have to practice in the moment, locating in your body when you feel that fear and breathing and staying and staying present in spite of it. And you can even say things like, you know, I'm just feeling really overwhelmed right now. I'm not I'm not going anywhere. But if you can give me 10 minutes just for me to breathe and recenter, I'd really appreciate that. I just need a moment.

31:00Or I'm not abandoning you, but I am feeling super overwhelmed. I want to reground myself. I just need to take a 15-minute walk. And I promise I will come back and you will have my full presence. Want to be the one who's always in the know about the game, the scores, the plays? Here's a tip. The Apple Sports app. Just pick your favorite teams and get automatic live updates without even knowing their schedules. And when your team scores, it shows up right on your iPhone lock screen, making it easy to check in anytime. So rule the group chat and download Apple Sports for free on the App Store or find it on your new iPhone.

31:38Is your home wish list just sitting in your cart? Well, get ready to hit checkout because Wayday at Wayfair starts October 24th with up to 80 % off everything home. That new sofa, the rug you've been eyeing, the upgrades you've been putting off, they could all be way less during Wayday. It's Wayfair's biggest sale of the year. So make your list and mark your calendar. Shop Wayday starting October 24th for up to 80 % off everything home at wayfair.com. Wayfair, every style, every home. Or if it's not as intense, you just breathe, you sit through it, and you just say, I'm here. I'm here. I'm not running away.

32:17Can we talk about this? And you get better at listening. and then you get better at communicating. And the more that you practice this, the more you're going to see that that fear, that monstrous fear that you feel, that feels all-consuming and feels like it's taken your agency away, that monster begins to shrink. And the more that you practice this, the more confident you feel in yourself. And the more confident that you feel in yourself to be able to be present and to stay grounded and to communicate, the better partner and person and human being you're going to become. No skill ever gets stronger without consistent practice.

33:12That is the law of the land. It gets easier with practice. That's also the law of the land. So the next question is, do you reach out to her? This is tricky because she laid down a boundary. And it sounds to me, based on your question, that you've crossed that boundary a couple times. And I don't want you to cross that boundary again. Yes, it's true that most women like their man to fight for them. but she's asked for no contact. Here's the thing. If you were to try to give this another go, you truly cannot do it unless you are very committed and have made the decision that this pattern ends today.

34:09And you would have to tell her that you are fully committed to not abandoning her during conflict. and that it's going to be a little uncomfortable for you. But what I would not do is send her or tell her a whole long thing about your trauma and why you do what you do. That doesn't help things. What helps is I've been doing the work. I understand why I've been doing this and I'm not doing it anymore. I'm not saying that I'm going to be perfect. I'm not saying that, you know, I'm never, ever going to disappoint you because we are sometimes going to disappoint each other. But what I do know is that I'm never going to fucking abandon you during a conflict again.

35:09And then you have to keep your word because the moment you don't keep your word is the moment she feels like she can never trust you again. I don't know if you should reach out to her. Again, I think you should be respecting her boundary. I don't know how long you've been no contact. I don't know what your agreement is. I don't know if your agreement is no contact indefinitely. I don't know. What I do know is that I know you love her, but I feel like this needs a little bit more time. and so maybe give it a couple months again i just don't know what the agreement was pushing back on a boundary is not very respectful and so she needs that and um and i don't want you to try to win her back in a state of desperation and where you're feeling ungrounded i really really really suggest that you get to the place where um you've made this decision that you're not going to do this anymore as uncomfortable as it is.

36:16And so again, I don't know how long you guys have been no contact, but I, I would give this, I would give this a little bit longer and, um, and maybe it'll work out with her one day and, but maybe it won't. In which case you will, you will fall in love again and you will, you will meet someone else and you will fall in love again and um and then you have the opportunity to practice this in a new relationship so i wish i could give you a clear-cut answer for this but i hope that i gave you enough information and enough insight into this for you to really um take this in even further and so that you can um understand yourself better and and have better relationships in the future because you deserve that.

37:04You deserve that. Jillian on Love is a Q Code production, executive produced by David Henning and Steve Wilson, produced and edited by Travis Howe. Music by Will Tendi.

37:20Want to be the one who's always in the know about the game, the scores, the plays? Here's a tip. The Apple Sports app. Just pick your favorite teams and get automatic live updates without even knowing their schedules. And when your team scores, it shows up right on your iPhone lock screen, making it easy to check in anytime. So rule the group chat and download Apple Sports for free on the App Store or find it on your new iPhone. Fall never arrives all at once. First the air, then the light. And slowly the things you love begin to find each other. A jacket meets a dress. A hoodie slips beneath a blazer.

37:58An old cap finds a new scarf. because you don't simply step into the season. You create it layer by layer until it finally feels like fall. Find fall your way at Ross.