How to Have Deep Conversations on First Dates

All right, today's podcast, we are going to be talking about conversations because have you ever dated a guy and you're kind of struggling with keeping that conversation going? Today we're going to be discussing this and giving you some easy strategies you can use to get that conversation moving. Welcome to the Love Strategies podcast where we help successful women attract high value men, date with a strategy and improve their relationships. Now, whether you're single or dating or in a new relationship, we're here to help you dive into the male mind and provide raw insights found nowhere else, backed by science, that and our own personal experiences. Your hosts today are myself, Adam Lodolce, professional dating coach and founder of love strategies, and Dr. Gary Lewandowski, a relationship scientist, professor, and our head relationship coach here at Love Strategies. Please share with a friend and enjoy. What do you think, Gary? We're going to dive into this one.

Love it. I love this topic. This is one of those topics that I came up with because so many of our clients have this complaint about guys on dates and having conversation is like pulling teeth. Like, they're just terrible at it. And so we have a little bit of a solution today.

Yeah, absolutely. I mean I, I'll say this to clients a lot because I used to coach men. You know, I went through about four years of my life of only working with men and these are like really powerful, high level guys who, who are very good in the workplace conversationally. But when they would go out at night, I would coach them on how to meet women just like all of you, and they would fall apart. They would just default to the most boring questions. Gary, you know what they are, right? What do you do for a living? Where do you work? Such fact based, like, oh, I would, I'd be listening to these conversations. I'm like, why do you always default to what do you do for a living? I hate that question.

When I think, you know, women, when they're out on dates, they default to many of the same questions. Yeah, right. Like I. The most common exchange I hear from clients is something along lines like, well, I asked the typical question, like, what do you do? And then he just basically says something really boring like, I'm the project manager at a mid sized regional health provider. And then the women just say, then I look at him, I'm just like, huh? And you know the guy just his only response to that is like, yep, living the dream. It's like, what? What the hell is that? Like, that is just not a fun first date conversation and it's super awkward. Because no one wants to. Like, you don't really want to ask him about his mid sized regional health service provider, blah, blah, blah. Like, no one. You don't want that. That's boring for you, tedious for him. And so how do we break out of these patterns?

Yeah, I mean, how do we do it? Because I, I do think dating in itself is such an awkward process because you're meeting someone brand new many times from a dating app, all you have to work off of is some text and a profile and a picture. You're basically talking to a stranger and trying to build some emotional connection. So it's like, how do we actually do all this? And one thing I know to be true is that memorizing some lines is not the way forward. Like, I would work with guys and they'd always be like, tell me exactly what to say. Like, give me some words. Everything like that. No, it comes off as just way too robotic and inauthentic. And so what we really hope to provide you today is some strategies you can use to be authentic, to keep a great conversation, to bring out the life within these guys. Because it exists. Like, these guys do have great personalities. We just got to bring it out of them.

Yeah. And here's the painful, unfair reality is that in a conversation on a first, really any conversation, but particularly a first date conversation, guys rely on women to carry the conversation forward. Is that fair? No, no, not at all. I mean, like, he should be doing his part too. But is this how it goes a lot of times? And the answer is yes. You know, if this was a podcast for men, we'd have a bunch of tips for men about how they should be moving the conversation forward. But it's not. This is a converse. This is a podcast for women. So it's, you know, this is not to say, you know, we're unfairly putting the burden on women, but let's just be. Let's just be honest. Like it's. You want to have some strategies for yourself so you're not bored to tears talking to this guy. So whether it's not necessarily for him, this is for you to make your first dates less terrible. Right. If you were with a guy who can't carry on conversation, and you know what makes those first dates so terrible and boring? It's like everybody asks the same things and that makes it feel like it's somewhat arbitrary. Like you're going through the motion and then you just kind of have this sense of like, I got to get through my roster of questions, my roster of topics to really figure this guy out. And then, you know, it just feels perfunctory, like you're just like, it's just not a enjoyable experience. And dating supposed to be fun. So let's fix it.

Amen. Let's fix it. And I just want to throw a big asterisk onto this conversation that is that if on a first meetup or first date with a guy, he's not a great conversationalist, it doesn't mean that he doesn't have a lot of value to add necessarily, because guys get very nervous on a first date, just as women do. People get nervous, But I think for men in particular, for a first date, like, there's a lot of pressure because they feel like they need to drive things forward and they need to keep the conversation going, even though they don't. And it actually kills their confidence quite a bit. So if we can work through just building those better conversations right off the bat, I think you're going to be able to have much more options in your love life. For guys who, once you kind of break through that initial barrier, they have actually a lot of lot to offer for you romantically.

I love that because I do think guys, particularly on that first date, what's constantly running through his head, endlessly looping is, don't blow it. Don't blow it. Don't screw it up. Don't say something dumb. Don't say something dumb. Don't say something dumb. You want to say something dumb, don't do it. Don't.

Yep. It's like, that's a classic. Say something dumb. Every first date. I had to.

Yeah, yeah. And the thing that goes through my head all the time and a lot of things is you're going to think this is funny, but other people may not just because you think it's funny. Maybe everyone else doesn't always think it's funny. So all of which is just to say, like, guys really do have some anxieties about conversation that they're bringing to the date. And so what we're going to talk about today is to put him at ease, put yourself at ease, kind of get over the going through the motions feeling and just really learn how to have more fun and ultimately get better information and insights into this guy. So you really have a better sense of how this relationship is or is not going to progress.

Well, let's dive into it. Gary, get us started, dude.

Yeah. So, you know, much to your point about, you know, this isn't about memorizing a bunch of Questions like, this is really a simple, simple strategy, and it's this differentiation between conversation starters versus connection builders. And so there's. There really are just two types of questions. The problem is we've only really ever gotten ourselves stuck on the conversation starters. Conversation starters are your standard icebreakers. Those are, you know, what do you do, where do you work, where are you from? These are super easy softball questions. The questions everybody expects. The questions. It's like a job interview. The questions everybody prepares for. These are a standard part of dating. Now, here's the thing. I just said people stick to these. And this is. There's mistakes that people make. Like, this is where most of dating happens. So one of the basic mistakes you can make with these conversation starters is some people get bored with them and they skip them altogether. They just never bother asking these things. Frankly, I get why you want to do that, but it comes off as weird. Like, it's a bit much. You can't just dive into what are your deepest, darkest secrets. Yeah, you have to have a little appetizer, a little warm up. You can't be too intense up at night.

Gary, what is your greatest fear? Like, what truly. Are you terrified of it?

Like, imagine.

I don't know you.

No, thanks. You have to get. He's nervous, you're nervous. Like, let's let everybody just have a simple softball warmup question. So, like, do not skip the conversation start. You're going to hear. We're going to emphasize a lot about the connection builders, but it does not mean you skip the conversation starters. The second mistake people make with conversation starters is they stick to those the entire time. The entire time. And you can't. Conversation starters are very superficial. Like, it's just basic. What's your fan? Did you have any brothers and sisters when you grew up? Where do you work? What do you like to eat? It's just. It becomes like the world's worst job interview. Like, it just. It is terrible, terrible, terrible. Which then leads to the third problem with the conversation starters is people don't like these. And even when people are asking them, they know it's not great. So they get into this rapid fire. Like, I'm just gonna power through this. I gotta get through my 10 list of questions to figure out, what's his previous relationship been like, you know, what was his family life? What's his work? It's like, no, like, the rapid fire approach just makes the whole thing, again, feel like the world's worst job interview. And that's just not the. Not the energy or the vibe you want on that first date?

Definitely not. Like, think of a really good conversation. What does it feel like? What does it look like? It feels like a dance. You know, you're kind of going back and forth. It's like he might be. Ideally, he's leading it a bit on a first date, it's likely what you want, and it kind of puts him into the masculine. But think of it kind of like a bachata or a tango. He's kind of leading it, but you're going along with it and you're on the same wavelength. But if you're just drilling him with one off questions that feel unrelated, the dance is like, that's like me on a dance floor on a Saturday night. You're just all over the map. Like you're throwing your hand in the air, then you're doing a kick, then you're doing a booty bump or like whatever it is, it doesn't work. So a good flow of conversation is key. That's like, it kind of builds on itself and. Yeah. Are you going to talk about the same thing the entire time? No, but like, I always think of it like a tree. Like a tree. You start with one core conversation and it kind of branches off. So you start from his hometown and that goes into his childhood and. And then it goes into his family life, and then it might go into what he's looking for in the future with this family, what's important. And I think a great conversation just flows that way. Rather than you ask him where he's from, then you ask him what he does for work, then you ask him, you know, what type of activity he likes to do on the weekend. It's like, it's all, where are we going with this? You know, it's no longer a dance. Don't be Adam on a Saturday night, drunk on a dance floor. Does this analogy work, Eric?

Well, I don't know. I don't know if that works, but. What? I'm a little sad or. I don't know, maybe it's. It's a good thing that the people that only get the audio of this didn't get to see you enacting live all those dance moves and on the video. I don't know, you're probably. This is might be a stick to audio kind of kind of podcast. But I do think that your metaphor of, of branching out is, is good because we really do want to branch out because we really want to go deeper. And that's where these connection builders come in. Connection builders are the questions that really evoke deeper, more personal information. It helps you learn more about this guy's character, how they think. It's about being thought provoking. It's about being emotion provoking. Like trying to like try to get into the guy's feels a little bit like, what does he feel about things? What is he passionate about? Getting him away from canned, typical prepared responses. I think of this very much as, you know, there's that philosophy like half as much, twice as well. And I think it's the same thing here with connection builders and your approach to dating. Get to know people is ask fewer questions and at least fewer topics and deeper, more powerful questions. Because I think one of the biggest mistakes I see clients make right is they try to gather a bunch of surface level facts that they can then take home with them at the end of the night and then do like this after date analysis of surface level facts either by themselves or with friends. And it's just like, let's tease this apart. He wore a plaid shirt, it was red. What does that mean? And it's like it all means nothing. And so let's just like ask him the deeper questions and find out what's going on.

Yeah, they'll like throw into chat GPT and be like, what does all this mean about this man? You know, he grew up in Chicago, but he actually roots for the Eagles. Like it's like, who cares?

Doesn't mean anything.

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It's like this like armchair psych, which is fun. Like I get it, like I, I, the psychology side of me loves the idea of looking at like surface level things and trying to figure out deeper meaning. And there's something really intriguing about that process. But it's often counterproductive because we're not right a lot of the time and we don't fact check ourselves. We're inaccurate and then we jump to conclusions, then we just go forward with those conclusions and it's a bad path.

Love it. So let's jump into some examples. I know you have a bunch of them. I think it'll be really helpful.

Yeah. And I think, you know, I mean, as we listen to these examples, remember the key here is it's not about gathering facts. It's about how he thinks his values, and we're also testing out his ability to have real conversations. All of those, by the way, are better predictors of long term relationship success than just gathering a bunch of facts. So, like, we want to see how is this guy going to be five years from now in our actual relationship by testing some of these things out. Okay, first topic. Probably one of the most common dating questions. And so what we're gonna do is we're going through topics, we're going to do a conversation starter, and then we'll talk about some of the connection builders. So typical conversation starter for the topic of like, where are you from? Is you just ask somebody, you know, did you grow up around here? It's a pretty good question. That's good. Conversation starter or where are you from originally? We've all heard those questions. So, Adam, what are better, better connection builders? How do we branch out from there?

I mean, the ones I got to just read them straight up because I love these, which is how do you think your hometown influenced who are, who you are today? Where else feels like home to you? Oh, that one's such a good one. It kind of gives me the chills because it's thinking, it's bringing me to those places and those happy memories right now. I can see how these are eliciting so much emotional connection. Or what is something special about your hometown that only local locals know or appreciate? Oh, my God. Townspa Pizza in Stowen, Massachusetts. Come on. That's the, that is the one place. And from where I'm from, those of you, the, the five of you that are listening, that know what that is, you gotta try it, you know, or that's a good pizza. That's a good pizza. But it just, it, it brings you to that place of. There's such happy emotions that come from those. Now, not everyone has a happy upbringing. And maybe it's not eliciting all those, those memories, but I think the one that particularly stuck with me is where else feels like home to you? Because I think everyone has some place that they've been that just does bring that out in them, brings that those happy emotions in them. So I'm a huge fan of these.

Yeah. And so, you know, we Won't do this for all of them. But just to kind of break this down a little bit. Like remember you're going to ask that original conversation starter, where are you from? Like where'd you grow up? Perfect. Kind of get them going but then you can transition over to where else feels like home to you. Here's the great piece of it. He has never heard that question on a first date. He hasn't prepared for it. You're going to get a real live, authentic. He's going to kind of like look at you probably wide eyed a little bit at first, like, huh. And then you're going to get authenticity because it can't be canned. It's hard to prepare and, and it's memorable. You want to be memorable, right on, on these end you're going to get a sense of how this guy thinks, how he feels, what motivates him, what gets him going. This is all good stuff. Like this is actually the kind of information you really want. And so that's the plan with all of these.

Also just the power of good questions. I just need to emphasize how important that is because you can be an incredible conversationalist without even talking much about yourself. Just asking really good questions that elicit a positive emotional response. I mean, I know when I was dating I would go on a few different dates once I started really working on my questions, I would ask people where we would leave the date and they wouldn't know anything about me. Like the woman wouldn't know anything about me, but she'd be like, wow, I really like you. I really enjoyed getting to know you. I'm like, you don't know anything about me and that's okay. Like it's okay. We're just, we're just getting started with all this and that's not a health necessarily a healthy thing. It's not like, you know, it didn't work out with those women. But it does go go to show the power of if you're just asking someone a question that does bring out the lightness in them, then suddenly they're going to equate that, like that lightness, that emotional response with you.

It's that old saying, it's like people remember how you made them feel, right? And it's like people like talking about themselves. We like opening up to other people. There's research that shows in relationships, self disclosure and opening what we call mutually transformative, which is really just a fancy way of saying the more you open up to somebody, the closer you feel to that other person. Because I've shared things with you. So now I feel close to you. Now here's the great thing. If I feel closer to you, I'm more likely to share. And around and around it goes. So sharing leads to closeness, closeness leads to sharing, and that is the stuff of relationships. This is why you want to get into these connection builders, right?

So, so should I do the next one, which is my least favorite question of all? Dating, which is, what do you do for work? That's a classic starter question. Or how do you spend most of your weekdays? Like, what do you do with your week, Gary? How can you turn that into more of a builder type question?

So for a connection builder, for those basic boring questions, I like, what's your ideal workday? Like, if you could design it from scratch, right? This kind of question gets to see, like, what do they prioritize? Like, what are they a hard worker? Are they gonna work a lot during that day? How are they gonna task switch? Like, what's really important to them? Do they work into their workday? Things like working out and, you know, quiet time and naps or meditation or any of that kind of stuff. Here's another one. If you could instantly master any skill for your career, what would it be? And then the last one, which is really important. I know a lot of our listeners are dating and aspiring to date high level successful guys. So I love this. What do you do to transition between work mode and relaxation? Because a lot of the guys are going to look at you kind of befuddled. Like, what do you mean transition? There's no such thing as transition work all the time. And it's like, where does a relationship fit into that life? And that's an important question.

I love these. I love these because you get to the heart of their life, which is what you're going for. Like, how do you spend most of your weekdays? You want to get a picture of what's important to them and their value systems. But like, how do you spend most of your weekdays? It's not going to get to the heart of it. But, you know, what do you do to transition between work mode and relaxation? That's an interesting one. Love to put on some music, have a glass of wine, maybe watch a really good TV show. Even if he doesn't do this type of stuff, he should say that at least. And, you know, maybe he talks about meditation. Meditation, if he's into that, maybe talks about going to the gym. Whatever it is, it gives you a much deeper picture of his life and what's important to him and his value system.

Well, you're also not. Not that this is all about gotcha questions or anything like that, but when you ask questions guys can't prepare for you, you're gonna get some unfiltered responses like, what do you do to transition between work mode and relaxation? Some guys are like, well, you know, I light a joint and watch Netflix.

Nothing wrong with that. Gary, come on.

Not saying there is. I'm just saying you're getting an unvarnished real take instead of, you know, I like to flip through the great books and listen to classical music. Like, you know, like there's something to the. Just like being a little bit unpredictable in your questions where you're going to get a little bit more authenticity. And that's what we want, right? So the next topic that we have on here, and that's a common one, is family dynamics. So a lot of times in conversation starters, people ask things like, did you grow up in a big or small family? Do you have any brothers or sisters? And here's the mistake people make with this. They find out, oh, they're a firstborn, oh, they're a last born or they're an only child. They make a bunch of conclusions, they don't follow up and they just draw a bunch of conclusions from that information, most of which are assumptions based on no facts or, you know, they find out the person's parents were divorced or their father died. And it's like, then again, they make a bunch of conclusions from that surface level information, again, which is all stereotypical assumptions, full of bias, all these problems. So Adam, what are connection builders in this area?

So we have, how would your family members describe your personality while growing up? That's a fascinating one. I've never been asked that question. I'd have to actually think about that for a minute before answering. But again, it brings me back to my childhood and yeah, that one puts me on the spot. Gary, or who are you most liking in your family? That's easy. My mom. What's the most valuable lesson you learned from your family? These are all questions that truly, Gary, in my entire life I've never been asked before and are kind of doozies. But they're good doozies, right? Like they make me think about something. It's almost building a new pathway in my brain where I'm like, I've never put those dots together and really thought about it in that way before. And I feel like that's the definition of a good question. When someone says, oh, that's a good question. That means it's something that they haven't thought about before. And it's just so well done, Gary. I gotta give you hats off on these ones.

These are good. So, you know, we've had other episodes about captivating questions and this, this is similar, but this is more. These questions are very specifically exactly what you just said, like trying to build some new pathways and someone who has asked you the question, what's the most valuable lesson you've learned from your family? And you have to think about that, like, that's gonna be a memorable experience for you. And you've had that experience with the other person and you just get to frankly see somebody, process how to be put on the spot like you just said, and work through it, live to see what that looks like and are they thought. I think the thing that this does the most, and it's something I talk to our clients about a lot, is intellectual curiosity is a big deal. Like you, most of, the, most of our clients, I suspect most of the listeners in this podcast are people who pride themselves on self improvement and growth and being better and learning new things. And so you want a partner that values that too. And so you will get to see with these kinds of questions, like, did they just answer it like off the cuff? Like now. They didn't teach me anything. Shutting it down or huh. I hadn't really, you know, you can answer it with. They haven't taught me anything in a more intellectual way. Like, you know, maybe I've learned some things about, I've learned some things what not to do. Right. I've learned, you know, there's a bunch of ways to go at this, but you really get like this real glimpse into how they are and how they think.

Yeah. Well, I think to, to save the listeners, I think we just kind of go rapid fire with the rest of those. That sounds good to you, Gary? And we'll, we'll give them a feel for the starter versus the builder. Yeah.

So you want to go?

Yeah, sure. So the next one is travel, by the way, everyone, 99% of people do like to travel, or at least we'll say that. So if you ask someone, do you like to travel? Everyone's going to say yes. But a builder question might be, Gary.

What destination surprised you for better or worse? And what's your go to first activity when exploring a new city? Boom.

You're gonna learn if he really does like to travel.

Right.

You know, talk about getting good information. Another one that you had here is mountains Versus beaches. Are you more drowned to a starter? Might be. Well, are you more drawn to the mountains or are you more of a beach person? Gary, what? Might be some builders?

Yeah, I think this is like a common question people like to ask about traveling. And so a builder, rather than asking just base, because mountain versus beach, it's like a one word answer, right. You're not getting a lot from that. So instead ask, how do you think your preference reflects your personality? And then what activities in that environment make you feel most alive?

Right, right. I love that. And then moving towards the questions that everyone gets to at some point when they're dating is the fun and entertaining questions. What kind of shows do you enjoy watching? Any series that you're really hooked on, Gary, how do we build off of that?

What I like is what's your comfort show like? Your comfort show is kind of like the one. Maybe you're a little embarrassed to say that you like to watch, but you like to watch it anyway.

Love is blind.

Love is blind. Mine used to be. Do you ever watch the show this is Us?

No.

Oh, my God. It's like a sappy drama. I think it was on NBC. I literally. This is embarrassing. I think I cried every episode. Every single one.

I love that, Gary. I love that you're.

Because it was about like the relationship and it was about the dad and his kids and being a good dad and it just, it, it would kill. So, I mean, you had learned some things.

All right, next time we have an event here in Boston, we're gonna watch that together on Sunday night. And I want to watch you cry. It's. We'll, we'll probably cry together.

I was going to say you, you're a crier too. You would. It gets you, man. It, it gets you. I also like the question, what show do you not like that everyone else loves? Like a little hot take, little, little controversy, like you know, just, just, just to kind of see. But I don't, you know, I don't necessarily think we, we need to go through a whole big list. I mean, I think at this point people get the, people get the idea, right? It's, it's about how do you start the conversation. You can, you should and can start with the basic questions, but rather than going rapid fire through topic to topic to topic and jump, jump, jump, stick on a topic, ask these deeper, more thought provoking questions. Here's the one other side piece of advice. You should have answers for these two. Have answers for yourself going in because he's going to he might completely shut down and be like, oh, my gosh. I really. Gosh, I have no idea. No idea. And then you can do something that. It's one of the most common things I say to clients. Give what you want to get. And so you give a little bit of your background about how your family has shaped something about you and your life. You've opened up, and now he has some time to think of something for himself. And the conversation goes from there.

Definitely. Energy is so infectious. It really is. And I'll say this to clients a lot when they're going on a first meetup with a guy. Always be prepared with some type of story from your day, because typically people will ask you, like, how's your day so far? It's like kind of an easy one when you're just meeting someone. How's your day? How's your evening been so far? It's like such an awkward. Just start a question. And if you can start with, my day was wild. Oh, my God. This morning I walked out of my house and X, Y, and Z. I don't have a story because I haven't left my house yet today. I'm still in my sweatpants at the moment. But you get the point. Having a great story that you're excited about, that can convey passion kind of sets the tone for the rest of the date. Because if you answer the question like, you just met the guy, it's a minute in he goes, how's your day? And you're just like, oh, my day's been okay so far. How about yours? Now that you've set the tone for the entire conversation as being this kind of, like, lame, transactional thing. So again, to your point, having great answers or thoughtful answers to some of these questions is very, very important. You can't ask him a doozy and then he has it back and you're like, I have no idea. I haven't thought about any of this.

Yeah, it seems unfair.

It seems unfair.

It seems unfair. But I think very much to your point about asking about the day, which is a very typical conversation starter, I think once you start getting this. This strategy kind of as your default way of doing things, you think, okay, I'm going to start off with how's your day? But then I'm going to quickly transition to, if you could create your ideal day, what would that look like? You know, just kind of very quickly go from the starter to the connection builder and just start doing that as a habit. You become much more interesting because you. We like people that ask us interesting questions. And so it's a really good strategy to keep that conversation going.

That's amazing. Well, I hope you all take these on your next meetup or your next date. Even if you've been with someone for 10 years, 20 years, be thinking about the starter question and then how you can go deeper building those connections. Because I'll tell you what, I'm going to bring some of these questions to my next date night with Jessica because I haven't thought of a lot of these questions, and I'm sure she has neither. And so I hope that this was really helpful for all you. Gary, this was fantastic and great. We'll talk to you all next week. Appreciate it, Gary.

All right, thanks, Adam.

So now you've reached the end of the podcast. Thank you so much for being here. And because you have proven that you are serious about attracting love, you wouldn't be listening to this podcast if you didn't feel that way. What I'd love for you to do is go to loveapply.com where you can apply for a complimentary love strategy session where a professional love strategist on my team is going to speak with you directly and be able to see whether or not our executive love coaching programs can be transformational for you and your love life. There's absolutely no fee whatsoever. All you got to do is head on over to loveapply.com schedule that session, and you could be speaking with someone on my team over the next couple days. All right, thanks so much. Talk to you soon.

Bye. Bye.