Is He Relationship Material? 3 Simple Questions to Ask Your Guy

I've sat across from a woman who's asking me like 10, 15 questions on a first date, just drilling back to back to back. And the whole time I'm thinking to myself, oh, she's been burned.

She.

She has what I call black heart syndrome. She. She's come from really rough, a really rough relationship, clearly, because she wouldn't be just drilling me with questions. And then you go out with another woman who just sits across from you, and you can just feel the warmth and the kindness and she comes from a place of curiosity, really. Just genuinely wanted to get to know me and understand the full picture, and I want to get to know her. And it's kind of lobbing the ball back and forth and it just has a flow. And I think that there's just such a different feel to those, those questions, even if you're asking almost the same questions. 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, psychology, 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. Gary, I think one of the most challenging things that people go through when they're dating is you go out with this person, I don't know, one or two, maybe three times, and the whole time you're trying to think to yourself, is this person relationship material? Is this person actually worth my time, my energy? Or is this going to be some narcissistic time waster who just sucks all of my emotional energy dry? And I think that's what we're going to be discussing today is few questions that you can ask to maybe save you a little bit of time throughout the dating process and determine if he is relationship material.

Yeah. And I think, you know what's really interesting about how you pose that is you can have, like, kind of all those questions running in the background all while you're having the most amazing fun time with this person who's just cool to hang out with, Right? You're going out on Friday and Saturday and, like, everything's great. You have a wonderful time. Like, you're smiling, you're laughing, you're all this stuff. But it's like, still, like, is this real, like, Is this guy really relationship material? And it. It's like one of those things that I think. I don't know. Like, I get asked this a lot, like, how do I know? How do I know for sure if this person is for real? And there's no magic test. Like, it'd be nice if there was like a phone on your app where you just kind of like, scan them, like a QR code, and you're like, yeah, yeah, this guy's awesome.

That's the trillion dollar business right there. Dude, we got to get out of coaching and just create that app, whatever that is.

QR code, simple face scan. This guy's for real or not. I mean, there's probably actually something to that with, like, biomarkers, anyway. Whole other thing. But I think that whole idea of, like, you know, are there, like, markers that you can kind of see kind of gets us into. We're going to get to those three questions that you definitely want to ask. But I think the first thing we want to do is go through some of the mistakes, and there are some common mistakes that people make in the pursuit of answering this question is, is he relationship material? And I think the first one, the first mistake is trying to read the signs.

Yeah.

And that sounds like, well, what. What the hell am I supposed to do if I'm not supposed to be reading the signs? But it's. This is an issue of what signs are you reading? And I think people are always, like, playing a little armchair psychologist with these things and are trying to read, like, subtle signs. Right?

Yeah.

And it's like a good sign might be, like, kind of digging into his relationship history a little bit. Like, what's. What's that been like? Has he been married? Divorced six times. Never had a relationship, never had a serious relationship. Talks bad about all of his exes. I think those are good signs. But, you know, you. You know from experience that there's some bad signs that people look at too.

Well, I was going to save this for a different podcast, but I feel like this is a perfect time for a little Adam rant, because there are things such as astrological signs. Oh, he is a Sagittarius, or I don't know, I'm a Gemini. Oh, he's a Gemini and I'm a whatever, so. Oh, no, I don't know if we're going to be a good fit or there's other s. I mean, we've been talking a lot internally about Mercury being in retrograde because I used to have someone who worked here who was A big fan of looking at, like, when Mercury was going around the sun and whether it's in retrograde and if that's a good sign for things happening and, and all of that is, is insanity. I mean, just looking at things like that to determine, and it sounds a little cuckoo saying this on a podcast this way, but people really do look at that type of stuff. And then on a more like, tactical level, I think a lot of signs people will look for that I think is really silly, are how often he, how quickly he responds to your text messages. Like, is he responding within 10 minutes? Oh, that's a really good sign that he really likes me versus he takes three hours to respond to a text message. No, that doesn't matter. You got to be kidding me. 10 minutes versus three hours? Yeah. For all we know, during that 10 minutes of delay, he's texting 10 other women. And then the guy who waits three hours, for all we know, he's really focused at work. He's doing his thing, he's working out. He's got an incredible life. So, yeah, this is, this is the Adam rant that I just. Let me get it together.

It's so funny, right? Because like, you look at text and we literally. I just had a client, it was like a week, maybe two weeks ago that I. She didn't come right out and say this, but I swear that behind the scenes she was actually charting texts and how many texts she was getting per day and which day. And I was like, I'm thinking, right, like, to what end? Like, oh, this week it was 9.5 texts a day, and the other week it was 8.76. Like, is that good? Like, as much as I love data, that's just the wrong way to go about a relationship. You're kind of focusing on the wrong things because like you said, what's behind those texts and why they're doing it. You don't really know. And so, yeah, here's the thing. And this is why it's mistake. Don't. Don't spend too much time trying to read these signs and like, trying to be clever about it and like, find these things that might mean something. Ask, just ask, Ask him to explain. Ask open ended questions. Because something I say all the time, the number one solution to every relationship problem, it's always the same thing, at least at first. Communication, communication, communication. You have to talk about it.

And so got it. And you got to do it in real life. Life in the real world, not in the digital world. Not going onto his instagram and looking at, oh, who's that girl that he has a picture with that he's posing with from three years ago? Why did he send me that weird emoji? Like the little sly, you know, face or emoji?

I don't know.

I don't know. Emojis, whatever. Why does he send me that little heart emoji? Does that mean something? Does that mean he likes me? Does that mean he doesn't like me?

No.

Who cares? We're not designed for that type of communication, real life communication, we've evolved over millions of years to be able to read the subtleties of how someone communicates with us, and that's where you get the real information. And so that is, I think, a really, really important point when it comes to this. And the questions we're about to ask. Tell you about. You got to do this in real life. You can't do this digitally, because you're just not going to get the wealth of information that exists when you actually talk to another human being in the real world. But wait, what if.

What if he used the exact same emoji in 2017 with this other girl? No, that's not a thing.

Oh, man.

That's it.

He's done. He is done.

Next. Next. It's so funny because, like, all of that Internet sleuthing, the Googling, like. Like, the record finding, like, that's so. Like, it feels good. It feels like you're doing something. It feels like you're digging into the past, but, like, you have to realize you don't know what you're looking at and you know why, and you don't know the backstory, and it's. You're filling in a lot of blanks, and that. That's a really dangerous place to be. And so that leads us to the second mistake, which sounds like the perfect solution. I just said communication. I think I repeated, like, three or four times. So it's. The second mistake is asking too many questions. Like, so many questions, like a bajillion nonstop questions.

And it's really him, just not as.

You know, Describe yourself. What are your strengths and weaknesses? Where. Where. Where do you see yourself in five years? Why should I date you? Who have you dated? It's like, it's like the world's worst job interview.

Yeah.

And that's not what we want.

It's.

It's. It's. It's got to be quality over quantity.

Yeah.

And.

And it's so much like the questions you just described. When you get into interview mode, it Comes from, like, your. Your intentions really matter, because when. When you're sitting across from a woman and you can tell her intention is to get information about you rather than actually connect with you and get to know the human being that you are, there's a big difference between the two, and there's a very different feel to it. Like, I've sat across from a woman who is asking me, like, 10, 15 questions on a first date, just drilling back to back to back. And the whole time, I'm thinking to myself, oh, she's been burned. She. She has what I call Blackheart syndrome.

She.

She's come from really rough. A really rough relationship, clearly, because she wouldn't be just drilling me with questions.

And.

And then you go out with another woman who just sits across from you, and you can just feel the warmth and the kindness, and she comes from a place of curiosity, really, just genuinely wanting to get to know me and understand the full picture, and I want to get to know her. And it's kind of lobbing the ball back and forth, and it just has a flow. And I think that there's just such a different feel to those. Those questions, even if you're asking almost the same questions. You know what I'm saying, Gary? Like, have you ever felt that when you're. When you're with someone, like, what has.

Your relationship experience been like versus what's your relationship experience been like? Very different. Because I think sometimes that second style sounds like you're trying to catch somebody in a lie or like you're trying. You're digging for dirt. Like, this is some kind of weird, like, expose interview. The first one, just like a general. Like, what's it. What's it been like for you?

Like, how.

How's. How's your past been?

Well, Gary, tell me about the last three women that you've dated and how did it end? And did you cheat on any of them?

How many were scor.

No, No, I can't do it with astrology.

I can't.

That is, like, one thing that I think our clients kind of hate about me is when I make fun of astrology. And the other one that I just. I can't stand. And this is gonna be a quick tangent is I spoke to a woman, and she was telling me about how she's gonna manifest her love life. Like, she's all about manifestation. And to her, manifestation was doing absolutely freaking nothing in her love life. Oh, I'm just gonna go about my life, and I'm gonna manifest him. Well, what does manifesting mean well, I'm going to keep telling myself he's coming. I'm going to look in the mirror, give myself some affirmations. And I'm like, like pulling my hair out because this is like the antithesis of what we teach you. I don't know. That's my, that's my rant of the day. Why am I in a ranty mood today? But it's just, it drives me crazy. Astrology, manifestation, affirmations, all that type of woo woo positive psychology. It's just not how we do things around here because there's very little science to show that that stuff really works anyways. And so much of what we promote is action, you know, taking real action. Hey there, ladies. As you can see, we're just getting this podcast off the ground. And since we don't run any ads, I only have one quick favor to ask in return. Can you just take a quick second right now, pause this episode and just leave us a review Wherever it is that you're listening to. The podcast really help us out a lot and it really does spread the love, love. And I think the world needs a little bit more of that. So I appreciate you. Now let's get back to the show.

Yeah, those things are just disempowering. Like it's taking away your own volition, your own agency, your own ability to like, really go out and like take ownership over this experience, which is really what, what people need to do to, to be successful.

Yeah. And like, we work with so many successful women, like really high powered, executive level women who are killing it professionally in, in many areas of their life. They tend to be very healthy. They tend to focus on, you know, their platonic relationships and so on and so forth. And in other areas of our life, we never say, oh, I'm gonna manifest this job by just sitting back and hoping that it comes to me. No, right, you're gonna go work it, girl. Like, you're gonna go make the that happen. And if a guy or anyone ever said that to me about anything professionally or female, whatever, gender, doesn't matter, I would just be like, absolutely not. Go take action. Go take a massive, massive amount of action and bring it to you. So I know this is a huge side tangent, but that kind of allows us to combine two podcasts into one. Because I was going to have one full podcast just on my rant and I've gotten it out, so thanks, Gary.

Work that out of your system. Your chakras are clear.

I feel like 10 pounds lighter right now. So thank you.

All right, well, I mean, to kind of bring it back to this is like we're, we're trying to set people up for success. And so the other mistake people make in it when it comes to asking questions is just ask. They, they don't ask too many questions. They're just asking low quality questions. And so you can go out with someone for weeks, months, talk non stop, but really never actually get to know them. And so those low quality questions, a lot of it's about like, you know, do you come here, you know, the classic, do you come here often? And they're just kind of talking about the place where you're going on a date and like, you can have a lot of conversation about the place that you're at and like looking at other people while you're there. That's not getting to know your partner. You can talk a lot about politics or celebrity gossip. That's not getting to know your partner. A lot of those conversations is just kind of like venting about work, right? Related problems and complaining about work or just telling stories about work. It's also, it's going to fill the air. It's going to fill a lot of time you're going to have, you're going to feel like this weird, superficial closeness, but it's not actually getting to know somebody.

I mean, when I used to coach men on how to meet women many, many years ago, I would help these guys who were really struggling in their love life, really nice guys who just didn't know how to flirt. I, I had a lot of experience with meeting new women and the two questions that women would ask in these scenarios constantly. And men are also guilty of this. So I don't want to say it's women, but in, you know, my experience with women is what do you do for work? And where are you from? And these two questions were like, when I would coach men and they were, and I would be next to them, I'd be like wingman manning them just to like help them in the situation. If they asked either of those two questions right off the bat, I would immediately pull them aside, be like, absolutely not. Remove those from your vocabulary. They are the most boring questions in the world. They don't create any real interest. And you're not really truly getting to know someone. I mean, yeah, if you're going to ask someone, you know, what they do for work, if it comes up later, sure, but at least ask them, well, why, why, you know, what made you choose that? You know, what do you find Interesting about that. It's dive a little bit deeper, get into the emotional side of it. And so I just think that is like the ultimate default that everyone goes to when they're asking questions, especially when they, they have a first meetup when they're online dating. It's like that's what they default to. And they wonder why they're not creating any real sparks and they're not really getting to know a person.

Right. And so, you know, we've talked a lot about the things that people do wrong and these are things that most people do wrong because they just don't know any better. Right. They, they haven't had the experience, they haven't had the knowledge. And so, you know, if you're doing some of these things, don't beat yourself up about it. It's very, very calm now.

Yeah.

Here are the three things you should ask and you're going to, you're going to see these are subtle questions. It's not like right in your face, but it's like these are the kinds of things you can ask and learn about whether this guy's relationship material. Without coming around, I'll be like, are you really shit material? Which is creepy. And so some questions you can ask, you know, you can ask better questions. You're going to have better conversations. So the first question we suggest ask is, is what have you learned about yourself recently? So Adam, what's that going to tell us?

Well, I mean, I think the big thing is do they have a growth mindset? Right? Have they actually, are they actually trying to learn more about themselves? Are they trying to be introspective? Are they introspective? And if the answer is no or they have nothing new going on their life, well, it's an indicator because at the end of the day, when you are considering someone for a long term relationship and you have a growth mindset, as in your focus on continual improvement, getting to know yourself, being introspective, you want to be with someone who's on that same level. So it's a very, very good indicator of your future potential together.

Yeah. And you know, you want long term conversation, not just for this one date. And so someone who's very thoughtful and like you said, introspective, they're going to have a lot more to talk about. They're going to be a better conversationalist long term and more than just for a date this particular weekend. So the second question we ask is, what was the last thing that made you feel like crying?

Big caveat on this one, I would not ask this, like, the first time you meet someone. Okay. Is a pretty intimate question. So I would certainly build a lot of rapport ahead of time. But I really like this question. I. I actually thought about this when Gary brought this to me for a couple hours. And I think it's so powerful to understand someone's emotional availability. If a guy is like, just kind of, like, quickly shrugs you off, just like, come on, cry. I'm not that type of guy. And he goes into that mode. Well, it gives you a little bit of an indicator. Right, Gary? Of where they're at.

Well, and we ask it.

We're answering the question.

Yeah. We're not asking when was the last time you cried? Because that can be a little tough for a guy, even if he does cry. Like, he kind of knows, like, that line of, like, is it okay to cry or not cry? And how much crying is too much crying is. Is a tough line. And this comes up. I'm a little bit of a crier. I'm a lot. A bit of a crier.

Right.

Like, we did the thing about the Notebook. I cried. I cried at the Notebook. I cried about a lot of things. But you want to ask this one as they. Just. When was the last time you kind of felt like crying? Because you want a guy who's comfortable with his emotions, can identify those emotions, knows where those emotions come from, and knows how to deal with those emotions. Right?

And so let's. Can we try it right now? Gary, other than the Notebook, when was the last time? How does it go? You felt like crying. When was the last time? Wait, let me repeat it just so everyone can use it. What was the last thing that made you feel like crying, Gary?

That's because I'm a little bit of a crier. The last thing was on Father's Day.

See, I knew his daughter.

Okay, you're gonna get me. My daughter, you know, gave me a handwritten card and said about, like, how. Oh, my gosh, I can't talk about this.

Oh, bring it. Come on, give it to me.

But it was just like, let me cry over here. Jesus.

I'm not a cry either. I. I came in today things where.

It was just like a gratitude. Thank you. Recognizing what I do for her, you know, it's just like. And, you know, she's. She's a teenager. You don't get those moments as frequently as I used to. And so, yeah, it's sweet because it means a lot to me. Right? It's like one of those things that's like really central to who I am.

Now everyone take a moment here, which is, this is a very sweet moment because I'm half crying too right now. This would be the answer to my question. This is the last thing that made me feel like crying is listening to you crying. Think about how much this just rounded out. Gary, in your mind. Imagine you were going on a date with a guy who is a single dad and that was the response he gave. Think about how much information I just gave you about him as a dad. It's. It's pretty powerful and it really kind of rounds somebody's their long term potential. And so Gary, I think you just got a lot of fans out there who want to.

I appreciate that study too. But you know, it's kind of like Adam said at the beginning, if this, this is a question, this is a tough first date question. But you know, I. Yeah. So if you don't want to ask this particular question right away, definitely back pocket it. Save it sooner rather than later. But you can kind of wait. But just be mindful of asking about emotions like tap into things that are deep emotions like vulnerability, shame, inadequacy, regret. Like regret is a good one to ask guys about because you have the power dynamics are okay with that one. Like they're not going to feel as vulnerable. Perhaps with regret. Inadequacy is a great question to ask. It's just that one's a little bit tougher as like an initial thing to ask about because it's a little. Guys can sometimes feel that as confrontational.

Yeah. Yeah. I remember I once went on a date with a woman. She was like, she was, I believe she was a therapist. She may have been a psychologist, you know, kind of, I, I forget exactly. But it was actually a really enjoyable first date. We didn't work out for many other reasons. But I remember the first date. I, it was right when I was starting my speaking career and she asked me what I do, which, you know, whatever, um, you know how I feel about that. But then I started telling her about my, my fear of public speaking and how I got really nervous and I told her about the situation where I like totally flopped on stage or whatever. And she's like, oh my God, like, how'd that make you feel? I was like embarrassed and I like never just her asking, like she's using her training on me a little bit. But it was like a nice moment where I'm like, know, I haven't really thought about that before. How did it make me feel? And it just, It. It created a connection point between the two of us in that moment because, I don't know, I'm sharing something super intimate with her that I never really thought about or shared before. Us guys, we're not going around typically thinking about our feelings. We're just not raised that way. I don't. I mean, society wise men are. The masculine energy is typically like, just push that, shove it down, don't think about it. Just power forward. And when a woman can kind of bring that out and you. And he feels like it's a safe environment to kind of open up about those things. Man, oh, man. Yeah. It's a great, great strategy.

So that's what that question is all about. Is, you know, seeing is he emotionally available? And so, you know, we're focusing a lot on the questions you can ask because obviously you have more control over that. But I would also kind of point out here, too, like, pay attention to the questions he's asking you about emotional types of things, because if he's emotionally available as a guy, he's also going to be more in tune with those types of things, and he's going to ask you, like, oh, wow, you had a hard day. Where. How did that make you feel? Like he's going to focus on. Is that frustrating?

Right.

And like, a guy who's emotionally available is going to get away from some of the basic, like, happy, mad, sad emotions and get into vulnerability, frustration, inadequacy, embarrassment, like those, like kind of those next level emotions. So pay attention to some of the emotion words that he uses as well.

Yeah, absolutely.

All right, so our third and last subtle question you can ask to kind of dig deep and figure out if he's relationship material is you just ask him, what's your biggest pet peeve? This is broad.

Yes.

Wide open. He gives him a lot of room to run with this. So what do you think, Adam? What are the good signs, bad signs with this?

Well, I might even take this a step further and say, what is your biggest pet peeve in a relationship? Because for me, that'll give me a lot of really good information about her, maybe even attachment style, let's say. Here, let me paint you two different pictures. I ask a woman, what's your biggest pet peeve in a relationship? And she says, oh, I hate when guys get super clingy. I just like when guys text me all the time, like, oh, that's such a turn off. Whereas let's say she responds to, what's your biggest pet peeve? Relationship. Ah, I Just hate when guys just disappear for a couple days and I don't hear from them. Interesting. Well, one might be avoidant and one might be Gary.

Anxious.

What do you think? Anxious. Yeah. Or, I mean, they could be both secure. It just might be the way they're answering the question, but it gives you a little bit of information there. It also gives you information about whether or not you would kind of vibe with each other. Like for me, if a woman says, oh, my biggest pet peeve is when I text a guy, he doesn't respond in 30 minutes, I'd be like, check, please. Wait, sir. Yes, check please. Because this ain't gonna work on it. Like I am one of those like 8 hour, 10 hour responders on texting. Sorry. Because that's just how I roll. So I think it's a really, really powerful thing to see how, how you kind of vibe with each other and, and then, you know, and then you just ask that question. It's, it's a fun, it's also kind of a fun question. Like pet peeves are kind of fun. It's kind of fun to vent a little bit about your pet peeves. So, yeah, that's, that's how I would think about that question.

Yeah, I think making about relationships is really smart because like you said, it kind of focuses you in on the right things. Um, and particularly like something like attachment. If you, if you, lady, if you have not become well versed in attachment. We have a previous podcast on this. It's really worth kind of digging into attachment theory, understanding what your attachment is so you can identify in yourself and others, because these kinds of questions that are quite revealing. And so it might be an automatic, you know, deal breaker kind of situation where it's like, oh, you don't want to deal with an avoidant guy. Right. So that, that just may be a personal preference. But it's also just some of the best information you can have to know your future path forward in this relationship and what it's going to be like. Because like Adam said, it's like somebody might have an avoidant tendency but still be secure. And so, you know, this is all just good information to have. So, you know, going forward, what to look out more for, what to worry about less and just kind of, it's. Everything's always is about, you know, the more knowledge you have, the better choices you're going to make. And so this is a great way to gain a lot of really important knowledge early on.

Yeah, I think questions are just, they're, they are the most important part of the first two to three dates of getting to know someone, it's like the quality of your questions are really going to dictate the quality of your connection. That's a quote right there. There you go, Gary. Put that up in a little. Pin it up. But the quality of your connections are based. Are. How did I say it? Are. The quality of your connections is going to be based on the quality of your questions. And one thing I would find personally that actually became a challenge after a while is that I would ask so many questions and really want to get to know someone not in the way like of interviewing drilling, but like, I was just genuinely curious when I was dating that I don't find that, like, women wouldn't even be asking me questions because I was just like, so much energy is that way. So don't be afraid. As kind of a bonus tip to leave space in the. In the conversation for him to also ask you questions. A little bit of silence is okay. That's healthy in a. Relate in a. When you're having a discussion with someone on a first date and allow that kind of energy to come back your way. Because again, if you are the type of woman that we typically work with, that kind of alpha type, take charge, you, you know, run it in the boardroom type woman who's just hyper successful, you likely have a way of bringing that interview energy, that penetrating more masculine energy to the conversation into the date. And that is actually going to not build rapport, it's going to break rapport. So allow that space to exist. Allow him for. Also get to get to know you. Allow yourself to let your walls down a little bit as time goes on and be vulnerable yourself and allow that emotional kind of shine through.

Yeah, that is actually a really important point because if you are someone who's kind of accustomed to being in control in your work environment or some other context, you're just very. It's very natural for you to ask other people questions. And you might even start in your personal life asking other people questions and without realizing it, doing it so that they won't ask you questions. And it's a way, like you said, to kind of keep up that emotional wall. It's like if I just keep peppering questions and finalists, they can't ask me anything and I don't have to be vulnerable at all. And that might feel natural because that's kind of the role you typically play, but that's not the role you need to play in a relationship. Right. It's got to be mutual. It's got to be shared power. You both have to be vulnerable. And so, you know, as much as you think, like, I just, I'm just being interested. I want to get to know them every once in a while. Like, some of those things that you're doing that seem like they're really heartfelt, intentional and wise and helpful might actually be concealing some other stuff that's going on that you're not so ready to admit to.

Yeah. Amen to that. Well, I really enjoyed this podcast. I think it's super important. And if you enjoyed this and you want more stuff like this, just leave us a comment below. This. If you're watching on this on YouTube and obviously feel free to subscribe and follow us on all the different podcast platforms. Thank you so much, Gary. Appreciate it, man.

Thanks.

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