Are You Sabotaging Your Dating Life?
3 May 2025 · 31 min
This podcast episode ("Are You Sabotaging Your Dating Life?") features Adam Lodolce and Dr. Gary Lewandowski outlining seven common dating mistakes that keep people—especially their target audience of successful women—stuck or "miserable" in dating. They frame the discussion by asking what actions would intentionally sabotage dating, then cover: relying on "love lottery" partners with many red flags; moving too fast physically/emotionally; overvaluing first-kiss chemistry instead of long-term compatibility; repeating a familiar but toxic "type"; prioritizing flashy dating skills and "shiny objects" over relationship substance; falling into oneitis instead of interviewing multiple partners pre-exclusivity; and appearing clingy/need-driven. The episode mixes research-informed perspective, client anecdotes, and calls-to-action for free trainings and strategy sessions.
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In today's podcast, we are going to be answering the question that I know all of you have been asking yourself, which is, how would you date if you wanted to make yourself miserable? It's a really funny question to ask, but there's actually a lot of importance to the, to this framing. We're framing this in a certain way because it's easy for us to continue to talk about. Here's what to do next, here's what to do next. Here's some strategies. We certainly coach our clients, but. But this framing actually makes us take a look at what not to do and what are some of the biggest mistakes we've seen from thousands of our clients. 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, a 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. And the interesting thing is, like, if you think about this in other terms, like health, if you're like, well, I want to lose weight, okay, great, you know, you can think about why I need to eat well, I need to do all these things, I need to exercise. But, but an interesting question that might hit you from a different center of your brain is what would you do if you were really overweight? What would your life look like? You'd be like, well, I would drink a lot of alcohol. I would eat like crap, I would not sleep. And so you just think to yourself, okay, don't do those things. So it's like, it's just a really interesting framing, looking at it from the opposite direction. And I know there's a very long intro to this, but I think I just wanted to present it that way because this, I think, will hit so many of you from a different angle and be able to help you take that action in your love life and get the results you're really looking for. Yeah.
And I, I know when we were talking internally about this topic, it was like, this is gonna be a little bit weird, but it's a good weird. It's a good weird because it's going to land just differently than a lot of the other podcasts that we've done about. Make sure you're Doing all these great things. This is gonna, you know, show you some of the big mistakes. And I think what's really interesting about the things we're gonna share today is the every one of them seems like it's a good idea. Like, it's got a hint of, yeah, I've seen other people do this. Maybe I should try this too. But we're going to show you. It's like, this isn't a good idea, like it's going to be a problem. And it's. It all comes down to the issues we've solved with so many of our clients. Right. That we've seen these things over and over and over again. And it's like people innocently say, well, I'm doing this, this, and this. And it's like, whoa. Well, that's actually what's keeping you stuck. That's what's keeping you a little bit miserable. And we're gonna do it a little bit different today. How to keep yourself miserable in dating. The question no one wanted to ask, but we're gonna answer, well, and so.
Much of success in anything in life, it's not about doing more things. It's about not doing the things that are hurting you. You know, it's actually about removal of things that are hurting you. Removing actions in some ways rather than adding more things to your plate. So today we're gonna be just going through the exact way to figure out how to screw up dating, how to make all those big mistakes that we've seen time and time again. We've literally worked with tens of thousands of clients over the past decade. And these are big cuz they seem like a good idea, but they really aren't. And obviously with all this, like, we don't want you to be miserable. What we do want is for you to recognize some of these behaviors that you might be doing that you know, aren't empowering you. And so the goal here is to help you think differently, make a change, and get things going. So, Gary, should we jump into it? What do you think?
Yeah, one. One thing that just popped in my head. I don't think I've ever talked about this on a podcast, but something I always joke with my relationship classes when I teach or even when I give, like, large lectures. There's something that happens when you're talking to a big group of people about relationships, and it's this thing I call the oh face. The oh face is you're sharing great information about what's good about relationships and the people that are in those Good relationships are just nodd. And you're like, yeah, they're smiling, they're having a great time because you're telling them all this great stuff about how they're doing all this stuff. Right? But then every once in a while, you talk about something that people are doing wrong that's making them miserable. And you see people in the crowd, they don't. The head shaking stops and they just go, oh. Like, they just have this look of like, oh, you're going to experience that during this podcast.
It's like when a baby poops their pants. Oh, oh, oh, no.
So, you know, I need to break.
Up with that person. Right?
You're definitely going to have the oh face or oh experience during this podcast, but in a good way. Because I think when we realize some of the things that we've been innocently doing that aren't actually paving our road to success, it empowers us to make a change in a way that maybe we wouldn't have realized some other way.
Right?
So all of which is a long introduction to the number one thing here, which is how did they completely wrong number one, rely on what I call love lottery tickets. A love lottery ticket is a guy who has a ton of red flags. He's got a bouquet of red flags. And you look through that bouquet of red flags and hope you see one in there that's not as red as the others. And you're like, I can make this work. This is possible. I can thread this needle. It's a one in a million shot. But I'm feeling lucky. I'm gonna cash in this lottery ticket. I'm gonna make it happen. And it's. It's like, I don't know, is it. This is dating myself a little bit. But there's a classic movie Dumb and Dumber, where he hears the odds of something and it's like, you know, what's your chances of going out with me? And it's like one in a million. He's like, so you're saying I have a chance? And I think that's how people date.
Dude, you are watching that so badly as. As like the number one dumb and dumber fan in the world that just.
It's something like that.
It's something like that. So you're telling me there's a chance. Okay.
Oh, it was. It was my acting skills you were taking issue with. So you're saying I got a chance.
I really appreciate the dumb and Dumber quote. It's fantastic. But it's really true. It is True. I mean, you look for just like, oh, my God, he is so perfect. X, you know, except you. He is just really mean to everyone in his life. And he doesn't call me for weeks on end. And he's also. But he's. He's really handsome, and he's great in bed. You know, I don't know.
I think there's an. There's another way that this happens a lot, which is he's revealed himself to be someone who is not a good communicator. He doesn't respect me. He doesn't seem to even really like me, but I think he can change.
Yeah.
And that's another Love Lottery ticket in the sense that, you know, something we talk to our clients a lot about is mindsets and how mindsets really matter. And so one of the ones that I'm a big fan of because it's a little bit statistical, is just this idea that just because something's possible doesn't mean that it's likely. Is it possible that this guy completely changes the way he is, the way he's been for the last several decades to miraculously make a major shift and become the man you want him to be and hope he can become? Is that possible? Yep. Is it likely? It's not freaking likely at all.
Yeah.
It's just not gonna happen. And so that's a Love Lottery ticket. Like, can you win the lottery? It's possible. It ain't likely.
Well, it's possible if you do it one time, but for those, maybe. But we all know if you play the lotto every day for 10 years, you will 100% lose every time. And for those listeners who have been in. In and out of relationships their whole lives, you just keep playing the lottery. And if you look at the odds on that, it's like going to the casino and playing slots. And they're really, really fun. And I'll do it, like, once a quarter, just, you know, I'll have a couple of drinks, play the SWAT slots and everything. And then I realize, no, no, odds aren't. It's not worth it, because the more you play, you're just. You're not going to. You're not going to hit. It's just. You're just going to lose in the end. So no more Love Lottery, which I think leads. It lends us well to the second one, which is, if you want to set yourself up for miserable dating, move really fast because you're super excited. It feels good. The thing is, it feels really good to just dive in Headfirst. But speed really does sacrifice quality. And this is a very timely one because I was actually on a mastermind last night with one of our clients who is an incredible human being. And we both met her. I won't say her name on this. And she. When she first started working with us, she's a bit older and she had a husband for 30 years and was widowed and never thought she could really experience true love at this age. And through our process, she's. She's met someone who she is so excited about. Like, she literally said, we went on a date. And he's the one. He is the one. We've been texting every day. We've been talking. We're already talking about seeing each other tomorrow and then the next day, and he's definitely the one. I'm so excited. I don't want to talk to other people. And it's like, this is the moment where I just want to say, like, I'm so happy for you and excited.
But.
And that's like a big old booty.
But.
Like a big old booty where. But have you listened to anything that we've been teaching for the past six months? You know, slow your roll, Slow it down. We have an entire little love step number five, little love step called little love step number five. And if you want to learn the little love steps, just go to lovestrategies.com, we just have a whole training there. It's. Feel free to check that out. Quick little promo there. But we have an entire little love step where it's focused on when you meet someone you're really excited about who potentially meets what we call your love vision. Slow your roll. As far as getting. We don't want to be getting physical too fast. We don't want to have the quick I love yous. We don't want to see moving fast as, like this early positive as a sign that it's 100% right. We're not going to call anyone the one really ever. Maybe until. Okay, if you've been married for 10 years and it's going really well, okay, fine, you can start using that type of romantic language. But let's chill until that stage and. Yeah, that's it. So I was a little bit of a romance killer last night, Gary.
Yeah, no, it's. It's the. I join you in the. In the league of romance killers. But it's. It's a romance killer, but a reality check. And I think the. The main reality check with this one is it does feel less romantic to say, like slow things down because everything feels so great if it's all so positive early on. And slowing things down, there's this fear that that means you're gonna lose something. But here's the thing is if you slow down, that's not gonna threaten something that is real, right? Taking a little bit slower actually just prolongs and extends the enjoyment, right? It builds a little bit more tension, it builds a little bit more anticipation. You get to savor, right? And like, let's savor this stage of our relationship rather than trying to rush through it and get on to the next thing. And, you know, if slowing things down causes a guy to disappear, he wasn't real in the first place and you just found out a lot quicker, which is important, definitely.
Why don't you take us to the next one, Gary?
So in addition to moving fast, I think something else that people do is always falling for those first kiss feelings. Now, first kiss feelings are amazing, right? It's a little lusty. It's like this nervous chemistry. It's part of connecting 100%, can't deny that. But it's not the part that matters most. It's not the feeling that matters most. What we really. And if you want to stay miserable, keep focusing on those lusty chemistry, butterfly tingles, all that kind of stuff and really prioritize that, make that the most important thing. If you always make that the most important thing, you will constantly be cycling through relationships and miserable. So the solution then is to focus on things that matter more, that are more long lasting comfort, authenticity, feeling, seen, heard, understood, respected, validated, cherished. Those are the feelings that matter. If you prioritize those feelings, you're not going to be miserable, right? And so feeling at ease, feeling safe, being yourself, it's let's not fall for the first kiss feelings. Let's, let's fall for the fulfillment feelings.
So one thing you'll hear a lot on the podcast is us mentioning the seven little love steps. These are seven powerful yet simple steps that you can take in your love life to attract that man that lasts for the rest of your life. So if you don't know the seven little love steps, then I have a free training for you. It's completely free. Just head on over, over to the lovesteps.com you can go through that virtual training. I think you're going to really enjoy it and get a lot out of it and understand our exact framework for attracting that relationship you truly deserve. Again, that's the lovesteps.com. all right, back to the pod. My, my friend. Oh, my friend Jamie, you know him, he sent me a viral TikTok video. I couldn't watch the whole thing, but I got to the point and the headline was why I always dump good guys. And it's actually like a dating coach who's doing this. So self proclaimed dating coach. But her whole thing is like if the first kiss and the first time you're with that person isn't like light your world sparks, then dump him, even if he's a good guy. And of course she's like 22 and dating coach. And look, I'm cool with that. I was a dating coach when I was 23. I'm sure I could go back in time. Like you're learning, you're kind of figuring out the world, but man oh man, bad advice, terrible. And I get like, I get the point. I understand it's an idealized version of love and I get it. We've all watched Disney movies and all of that and that's easy to teach. When it comes to coaching, I think the hard thing to coach on and I know this is like really convenient because we are coaching on it is like deprioritize that stuff. Right. You know, like that's hard. That's like. To tell someone is in some ways going against human nature, but it's not human nature to be in a 50 year marriage. So maybe we have to look at it a little bit differently.
Yeah. And sometimes you need to hear things you don't want to hear because that's actually what's good for you.
Right, Right.
And like that's that, you know, it's why we hire personal trainers, it's why we go to see the doctor. Like sometimes you need that those people to tell you the things that it's a little harder to hear, but it's, it's much better for your long term. And so you know, that person giving the first kiss feeling as determinant of relationship success. That's easy quote unquote advice to give because it's what people want to hear and believe in. But it's actually not helpful, which I mean is a, is irresponsible at, at best.
So you're saying we're not going viral with this point? I don't think we are.
No.
But that's okay. We, we reach a much different audience, which is fantastic. Another really important point, the fourth one is if you want to stay miserable in dating, just keep dating your type. Keep dating the same type of guy that you've been dating. If that's what worked, it would, you know, but the reality is, like, if that worked, it would have worked by now. Like, toxic partners are often your type because they're familiar in many ways. We don't date in a way to set ourself up for success. We date in a way that makes us feel comfortable. And if you grew up in a family life or you're used to dating people who are toxic and they talk to you a certain way, although it is not good for you, it will feel comfortable for you. And the crazy thing is, we have so many clients who are so used to dating toxic partners that when they start dating a really good guy because they follow our process, they're always like, man, this feels really uncomfortable and really weird. I don't know if this is legit. Like, he's been opening up to me. He actually brought me flowers last week. Adam, what's going on? Do I need to leave this? And I'm like, no, no, you don't. You don't. It's gonna feel weird. It's gonna feel different because it's not your pattern. And that's a good thing.
Lean in.
Don't run away. Lean in.
Yeah. And it's. We start mist. And you know, I've heard clients say very similar things. And it's like, this guy's kind of boring.
Well.
And I always ask, well, what do you mean by boring? And then invariably their description of boring reveals a man who is consistent, who follows through, who's predictable, reliable, stable, all the things that you want. I literally just last night on a mastermind had somebody talking about this idea in terms of physical intimacy. And she was saying, you know, she never has problems with this. Like, she. She's committed relationship with this guy for several months. They're now in the. In the realm of physical intimacy. And she's like, I've always. I've never had any issues with this. But this guy did something that was really unsettling, like, oh, gosh. Oh, no. Like, dear, dear God. Like, what did he do? Well, you know, in the mid week, we were, you know, kind of going through the. And then he asked me what I would like, and it just threw me off completely. And I was like, this is weird. I don't know, like. And I was like, this is a champagne problem.
That's a good thing.
This is a good thing. And. But it's like, this is such a good thing that for a lot of people, hearing this pod is like, they're like, oh, this is a great thing. Of course, like, all guys do this, but then there's also a whole bunch of people that are listening. No guy does this. No guy ever would do such a thing. And it's like your past experience shapes so much of your expectations. And like, just because you've been dating a certain type and you think, oh, no guy would ever ask. That's not true.
Right.
It's just, this is why it's so important to go against your type and just try some. Some different things break out of your comfort zone, as we often say, because one of the greatest gifts you get in terms of dating is realizing that everybody's not like your ex.
Yeah. Which actually, I think leads us, well, to the fifth point, which is, please, dear God, if you want to stay single and miserable while you're dating forever and be that weird cat lady down the street later in life, continue focusing on what we call the shiny objects. That's things that are really easy to see but really don't matter as much. It's the guy who's got that Rolex watch on that first date. He's flaunting and he's talking about that boat he just bought. $100,000 boat, and he's got that dock in downtown Boston. And let me tell you that you got to know some people to have that doc. Okay? The smooth talking, charismatic, charming guy who loves to bring you gifts, who loves to have these just grand gestures just like right from the movies. He loves attention. You walk into the restaurant, he knows the owner, he knows how to compliment a woman and tell you that you're the most special pretty thing he's ever seen. Keep dating that guy and focusing on those objects and not the things that really matter in a relationship. Keep doing that.
That's it. I. I have to just say how much I appreciate you are so into this. How to make yourself miserable part of this. Like, you're. You're doing such a good job.
Stay miserable, stay miserable. You're doing such a good job of.
Like, leaning into the, like, you know, going for it. I love it. Right. I'm gonna try. So if you really want to be miserable for the rest of your life, keep. And this, this joking aside, super sick. Keep going. For the guys who are good at dating, right? Like, when you're dating, there's this weird temptation to really focus on how good the dates are in terms of where you're going, how fun they are. Just, it's like that. Are they bachelor esque? Are they like that special and it's, you don't want to go for the guy who's really good at dating because you know how he got good at dating? Did a lot of dating. Guys who did a lot of dating, guess what? They didn't do a lot of. They didn't get a chance to really exercise, learn long term relationship skills because they've been spending all their time dating. And so dating skills are different skill set than relationship skills. They are not the same kinds of things. And so if you want to stay miserable, keep prioritizing, optimizing, being impressed by a guy's dating skills. Because some of the world's best daters are some of the world's worst relationship guys. And so let's not forget what we're really out there to do, which is I say to clients all the time, we don't want you to get good at dating. We want you to date long enough to find a guy who's good at relationships. And that's a very, very different thing, right?
Yeah, I mean, it's. I've heard this so many times from clients where they're like, I wish I could just go out and a guy would just approach me and just win me over. And they're subconsciously or consciously looking for the guy who can do something like that. See a woman from across the room and within a few minutes win her over, be that smart, charming, really funny guy. And the reality is, and this is coming from a guy who used to teach this for a living for five years. The only guys who are good at that are guys who are very, very well practiced. Like, it is not easy for a man to learn that skill. It's very, very challenging to walk over to a person and within a few minutes build enough attraction and interest that that woman continues to want to talk to you. That is like a level 10 out of 10 really difficult skills. And I just think of all my closest friends who are really good guys, who have a family now who are really committed to the relationships. They were so bad at that. Like, so, so, so, so, so, so bad at that. They just couldn't do it. They couldn't do it. So let's not optimize for that. Give these guys a chance who might be a little bit awkward, who might be awkwardly looking at you when you go out, when you go on a meetup. And they, the first couple questions are like a little weird because they're super fidgety and it's off. Give him a chance. He's just getting things started. You're not actually getting to know the real guy anyway. So give it a little bit of an opportunity. Let things develop.
I love making the parallel with dating to looking for a job or finding a career because, you know, becoming good at dating is like someone who's good at interviewing, right? It's like, how do you get good at, like really good at interviewing? Well, you go on a ton of interviews. Well, why the hell are you going on a ton of interviews? Well, because you can't hold down a damn job.
That's a me that now that's a viral one, Gary. That's a good one. I totally agree with you.
That's like, it's just like one of those things. Like if you think of. Sometimes we just have to think of the parallels in other contexts to just realize how ridiculous it is what we're looking for when we're asking of these people. Like, I don't know. So very much related to the interviewing thing because I do really love this metaphor. Is so number to be miserable. Focus on only dating. Talking to one person at a time.
Right?
All your eggs in the same basket. And again, think of it like an interview. If you're really looking for the. Your best career match moving forward, your, your long term fulfilling career, are you going to apply to one job, see how that process goes before waiting to apply to job number two if see how that goes? No, because that is inefficient and not going to lead to the best outcome. What do you do? First, you make sure that you're a decent enough match with these companies that you're applying to. You're going to apply to anyone who seems like a decent match. You're going to start going through the process with each of them to learn more about the company, have them learn more. The parallel is amazing. And so what we encourage our clients to do is talk to multiple. Get to know several guys at the same time. If you want to be miserable, get what we call oneitis, which is you lock into one guy, focus on him. And the problem with oneitis and focusing on one person is you become more and more invested in making it work.
Right.
I'm talking to this guy now. I've been talking to him exclusively, just him and I, for a month. Gosh, I don't want to waste the past month because I've been talking just so now I'm going to start forgiving some things that I shouldn't really overlook. I'm going to start settling in some areas I shouldn't settle because now I'm invested And it just. You end up wasting more time that way.
Definitely it. And just for those who are new to the little love steps, it's a very important point here, is this. This only applies if you're not exclusive. So if you are exclusive with a person, and we call that little love step number six, then that means you and him are an exclusive relationship and you will only be talking to and dating him. Right. But before that time where you have that conversation about exclusivity, continue talking to multiple people at the same time. It's similar to the job situation. Once you sign an offer. Yeah. Stop the other interviews, right. You got the job, you got the bonus. You got the signing bonus. Let's go. It's happening. You cancel all the other interviews, but until that offer is signed, check received, or whatever it is, you continue interviewing throughout the whole process. Because guess what? Don't get jobitis. How about that, huh? I like it.
I like it. I like. I see what you did there.
Yeah, yeah, definitely. So equal to little love steps. And if you want again, free training on that, we have that@lovestrategies.com we walk you through the entire process so that you can really get out there and set yourself up for success.
So our last one, Save them. Save the best for last. Like, this is such a big one. If you want to stay miserable in your dating life, you want to stay single, you just have to be a couple things, and that is super clingy, needy, jealous, and desperate.
You.
If you're clingy, needy, jealous and desperate. And a few bonus points in there, if you are all about drama, you're going to be miserable. And not only are you going to be miserable, you're going to make every person you date miserable, and you're going to end up not wanting to date anybody, and no one's going to want to date you. And so what we can say, what I can say with 100% certainty is every man on the planet finds a partner who is clingy, needy, jealous, and desperate. And dramatic. Exhausting. Exhausting. And it's one of the things that everybody wants from a relationship is someone who makes their life easier, better, and enhances their existence. But if you're clingy, needy, jealous, and desperate, that ain't happening. And.
And just to save the comments here, if we had a podcast for men, and I used to coach men, don't worry, we would be saying the same exact thing. So if you're thinking to yourself, well, why are a couple guys saying to women, don't Be clean, clingy, needy, jealous, desperate. It's because we're, we coach women. That's what we do for a living. That's where we focus our attention. But trust me, if you were dating a guy, would you want him to be clingy, needy, jealous and desperate and dramatic? No. So get the hint. Like it goes both ways. So sorry, Gary, I just had to.
Have a quick no. I appreciate, I appreciate it because I didn't want the negativity addressed towards me because I was one saying it. But you know, I think it's like, what is clean, needy, jealous and desperate look like? Lots of texting, lots of reassurances, needing to spend every possible moment together. What are you doing? Who are you with? Can I come? Oh, you're going to go see your friends. Can I come? Right. And again, if it was a guy doing that to you, you'd hate it. Hate it. Or you should, right? And you should not do the same thing to him. And it's like everybody likes attention. That's part of why we're in a relationship. But it's something with how we look at relationships. Here is the whole idea is you are a full, complete, amazing person. Your partner is a full, complete, amazing person. And the magic happens when you both get to share your full, complete, amazing lives with each other. It creates this synergistic experience where the two of you together are something better and more profound than you could be by yourselves. And that is each person facilitating connection, not needing, demanding in a desperate, jealous, dramatic fashion. Please pay attention to me and make me feel better about myself.
Definitely. So for those of you who do want to stay miserable, just keep following these principles. Keep doing that thing over and over and over again. But for those of you who want to change in your love life, don't do these things. Let's follow a proven strategy. We're here to walk with you every single step of the way. In the show notes, we have an area where you can apply to speak with someone on our team. Go ahead and click that. We're happy to jump on a love strategy session with you, see if we can help you change these behaviors and set you up for long term success. Gary, that was a lot of fun, man. I hope maybe we'll do a part two on this because I think we got a lot more.
I have so many more to share. So many, so many, so many more.
So if you enjoyed this, send this to a friend and if this one gets an outrageous number of downloads, we'll do another one. So go ahead and share this one. Thanks, Gary. That was fantastic. I appreciate your time, man.
Awesome. Thanks, Adam.
All right. Thank you so much for being a part of the Love Strategies community. By getting to the end of the podcast, you have proven that you are a high value woman who deserves a long lasting relationship, and we would love to help you get there. So what I recommend you do is go to loveapply.com and you can claim a free love Strategy session where someone on my team is going to get on a call with you on a zoom session, be able to understand your challenges, and see whether or not we can help you make that a reality this year. So head on over to loveapply.com apply for that free love Strategy session, and we cannot wait to help you attract that man you truly deserve. All right, thanks for being here.