Questions On Serial Dating & Avoiding The Player Label

Questions on serial dating & avoiding the player label & bad reputation that goes with it.

In this video coaching newsletter I discuss an email from a 33-year-old viewer who says he’s read 3% Man over 15 times and been following my work for four years. He’s a digital nomad and completely leans on dating apps to meet women. However, he’s introverted and not very good at approaching or starting conversations with women in person.

He also worries about being labeled a player because women find out he’s a serial dater and not looking for anything serious. My comments are in bold italics like this below in the body of his email.

This particular email is from a 33-year-old digital nomad, and he says he’s read 3% Man over 15 times and been following my work for about four years. So he’s got, I guess, some issues and he’s got three different main topics that he wants to go into.

So he tends to go from country to country. It doesn’t seem like he stays in one area for very long, or maybe he’s got a home base and he’s just traveling all over the place. So he exclusively 100% relies on dating apps to meet women. The problem is, is that when it comes to meeting women in person, he’s not very good. On top of that, he says sometimes women are calling him or labeling him a player, and he wants to know what to do about that. So he’s got a bunch of questions here and we’ll just kind of go through them.

Viewer Email:

Hi Coach,

My name is Bob. I’ve been a dedicated student for four years now, read 3% Man over 15 times and still revisit it on Audible 2–3 times a year to keep it fresh. Your work completely changed my dating life.

I’m a 33-year-old successful man, in great shape, living the life I always envisioned. About a year ago, I ended a great relationship because I realized I wasn’t ready for anything serious, or at least I haven’t met someone who’s made me change my mind.

Well, if you’re with somebody and they make it so good, they’re so easy-going, easy to get along with and be with, and they fulfill you and you feel content, you’ll stay with them. If you don’t, you won’t. You’ll move on.

Right now, I genuinely enjoy dating different beautiful women. I consider myself pretty skilled with women at this stage, but I have a few questions I’d love your take on:

1. Avoiding the “player” label:
   I date openly, respectfully, and never lie to women about exclusivity. That said, I live mostly outside the U.S. in cities where the dating scene seems to be pretty interconnected. So women usually find out — Or at least suspect — that I’m seeing others.

Well, the other part of the downside is if you’re only relying on dating apps, remember there are those Facebook groups that are, “Are we dating the same guy?”

So if you’re going to be on a dating app and you’re just constantly burning through girls, especially if you’re burning through girls and hooking up with them, and then they’re walking away with a sour taste in your mouth, eventually you’re going to come across one who’s going to probably post about you, and that’s again the downside. If you only lean on dating apps, like this guy does, because it sounds like he’s a little introverted and socially stunted in person, it’s just easier for him to meet on the dating apps, but part of the problem is because he’s always fishing in the same waters, he’s starting to come across the same women or women that know each other, especially if the cities are kind of small.

Again, there’s a lot of women that are creating these pages, “Are we dating the same guy?” Is a very popular one. So you could have one date that doesn’t go well, and the girl could go there and blab and that could cock-block you.

While that sometimes works in my favor (“When the kitty cats fight, you win”)…

It’s actually, “When kitty cats compete, you win.” Not when they fight.

…I’m starting to wonder: Is there a tipping point where being too active starts to backfire and damages my image?

Well, are women walking away from their experience with you, think of what a great guy you are, or what a selfish dickhead you are? Because if it’s the latter, you’re going to have problems because again, you may end up posted on one of these sites. If you use the same routine, because again, as you’ll see when we get to the third question, he’s not very good in person, even he can kind of start a conversation, but after that he has a hard time maintaining it. So more than likely he’s kind of got a routine as to what he takes women through when he goes online dating because he’s just trying to smash.

So that tells me he’s really only focused on the pickup and the dating skills, but didn’t pay any attention to the relationship stuff because he just doesn’t feel he needs it. So if you do that, you’re going to come off as very cold, and when you do meet somebody you really like, it’s going to be hard for you to maintain it because your relationships and your interactions are just very surface level. They’re not very deep.

Some women are beginning to see me as a “playboy.” Is that necessarily bad? Or can that reputation be a liability long term?

Again, if you’re being posted to these pages and you’re only exclusively meeting women online, then that could be a problem. Especially, are women walking away thinking what a great guy you are, or what a dickhead you are?

Any tips on how to date frequently without creating the “man slut” impression?

Well, operational security and meeting women in the real world instead of exclusively relying on the dating apps.

2. Balancing lifestyle and expectations on dates:
You advise keeping early dates simple, which I understand and follow. That said, I’m financially well-off, and what’s “normal” to me — Exclusive rooftop bars, nicer restaurants, and after a few dates, occasional weekend getaways — might come across as extravagant to women who aren’t at the same financial level.
I’m mindful not to let money be the reason a woman is attracted to me, but my lifestyle (Where I live, travel habits, etc.) sometimes gives it away. How can I draw a healthy line here — Where I stay authentic but don’t accidentally lead with lifestyle or money?

Well, meet women where you hang out. You got to start meeting women in person. That’s a big part of it.

Again, if you’re just exclusively leaning on dating apps, then you’re getting women from all socioeconomic backgrounds. The reality is, if you’re doing well, like me personally, I’m not going to go and do a coffee date with a girl because I’m trying to save money. If I’m going to go eat somewhere, I’m going to go eat at a nice restaurant where I can have a nice meal and nice company. So if that’s your lifestyle, you should enjoy it. You should embrace it and be proud of it. If you meet women that are also hanging out in those type of social circles in person, then that really should be a non-issue, but again, if you’re just exclusively only going to talk to women you’re meeting on dating apps because you avoid women in person, well you’re kind of painting yourself into a corner and limiting your options there.

I don’t think I am being extravagant since these are places I frequent and enjoy but wanted to get your thoughts on this. 

3. Improving real-world approaches:
I meet most women through dating apps, especially since I travel to different cities and countries every 2–3 months and apps let me connect before arriving. It works well for me — I date about twice a week, which fits my schedule. But I’ve realized I want to build more skill with in-person approaches, especially for women I meet at the gym, boxing classes (One of my hobbies), or just walking around. I’m naturally confident and social, but more introverted than I appear, so I tend to default to apps for efficiency.

I would say it’s because of efficiency. It’s because it’s easy, and quite frankly, you’re too timid and shy to meet women in person. So that tells me you’re a younger guy, so you’re kind of socially stunted. You’re traveling in a new city, so you’re probably not hanging out with friends or people. So you got no social circle, no social group. That’s the problem of being a digital nomad. You’re a stranger wherever you go, which being a man of mystery can work to your advantage, but if you only will talk to women, if you meet them on a dating app, then you meet a girl in person, you’re just going to choke.

So if I were you, what I would do is stay off the dating apps. Force yourself to only meet women in person and talk to women. If you’re having a hard time with that, because as he says…

I can start conversations easily (Asking for opinions, smiling, etc.) but struggle to take things further. For example, turning regular eye contact at the gym into something more.

Well, that tells me you just have not practiced your social skills at all, and you need to get in the habit of that. You need to get in the habit of going out and wherever you go, you’re the life of the party. When you see people, especially if you’re traveling, “Hey, where are you guys from? You live around here or are you an expat like me? Where are you all from?” Especially when you come across women that are also from the States, again if you do well and you hang out in the areas where other people do well, you should meet other like-minded guys you can become friends with and women that you could potentially date.

What steps would you recommend to improve at this for someone who’s not necessarily a beginner at talking to women?

Thanks as always for the great work. It’s had a huge impact on my life.

Best,

Bob

Well quite frankly, the way you talk, you are definitely a beginner, because if you see a woman in a gym and you’re like, “Gee, what do I do about that?” Well, you’re a beginner. You’re an amateur when it comes to meeting and talking to women in person, just because you haven’t practiced small talk. That is something that is absolutely essential, and for you younger guys that have always relied on your digital devices and dating apps, it’s going to be really hard to do that, especially now that you’re in your 30s.

So again, if I were you, I would be out constantly and trying to strike up conversations with people anywhere and everywhere. Not just the pretty girls that you have interest in, but other human beings in general. That’s what you’ve got to do. You’ve got to rehearse it. There is a video that I reference in the book, that’s in 3% Man, Improving Your Social Skills, The Process Of Improving Your Social Skills. I suggest you watch that and go do it and immerse yourself in it, and force yourself to stay off the dating apps and only allow yourself to meet women that you meet in person, because what you do often, you do best, and I could tell you’re avoiding real world approaches and interacting with human beings in person. To just not even be able to have a small talk conversation with a woman just tells me you need to practice your small talk and you just haven’t done it enough.

Repetition is the mother of skill. Force yourself to do approaches every week. Ideally, if you got two days a week, spend four or five hours each day doing nothing but cold approaches and striking up conversations with anyone and everyone wherever you go, because you have to get to the point where that’s like breathing to you. Like it’s not a big deal. In your case, since you don’t practice it and it’s very clear from your email that you avoid it at all costs, when you meet somebody you really like, you don’t know how to take it further because you never practiced making small talk with people in person.

So that’s what you’re going to have to do. Get in the habit of asking sincere, authentic questions, taking interest in other people, because if you can’t, if you meet a girl and you’re able to open her up but then you can’t take it any further, what do you think is going to happen on a date? How are you going to carry a conversation on a date? Unless you’re just going to have superficial conversations. So again, you gotta practice this stuff.

I know you’re trying to avoid it at all costs, but you got to participate in your own rescue. If I were you, I would force yourself over the next 30 days to stay completely off the dating apps and only meet people in person. Again, you get in the elevator, talk to somebody, talk to the people in the elevator. If you’re sitting down in a restaurant, ask some questions about the people that are just waiting on you. Tell them that you’re new to the area and, “What’s there to do for fun?” Ask them their opinions on things and just strike up a conversation.

Again, it’s taking a sincere, authentic interest in other people. Ask people questions that are sitting near you. Go to social events. If you love golf, join a country club. If you love boating, join a yacht club. Point being is, join some organizations or some clubs that either, like you got money you say, so go hang out with other like-minded people with money, hang out and you’ll start finding people you can become friends with and you’ll find women that come from a higher socioeconomic background instead of the ones that you’re meeting on the dating apps. If you think about it, if a girl is very attractive, she’s got a big social network, she has lots of friends and she’s a very social person, she’s going to meet lots of guys just through her life. Women like that tend to not be on the dating apps, because they don’t want to deal with the garbage that you have to deal with on the dating apps.

So women that got issues, there’s going to be a high incidence of them on the dating apps. You’re just going to have a better experience if you meet women in person, but you got to get in the habit of wherever you go you strike up conversations with people everywhere. You’re just not going to be able to get around it. If you want to be better in person, you got to practice. Immerse yourself in it. Force yourself twice a week, spend four or five hours just talking to strangers and doing cold approaches. If you do that, you can do 10 to 12 cold approaches in four or five hours easily. You do that for two days, that’s 25 different women. You do that every week, that’s 100 a month. If you cold approach 100 different women a month, you typically get 10 to 12 or 13 dates, and out of those, if you’re following what’s in the book, three to five of them are going to end up sleeping with you. Those are just the numbers.

So I know it’s the last thing you want to hear and probably the last thing you want to do, but stay off the dating apps and go interact with other human beings in person exclusively and force yourself to strike up conversations with people, even though you might not want to talk to them. Old couples, married couples, families, other guys that you see, girls that you see, groups of women. You just got to get in the habit of being interested and asking good questions and becoming the life of the party. There’s no getting around it.

Yeah you can be in the dating apps, but it’s pretty clear you’re just cycling through a shit ton of women. You’re not really digging any of them, it sounds like. It just sounds like you’re having a lot of superficial interactions, meetups and hooking up with girls, and then after you hook up with them, it’s like another notch in the bedpost, and then you’re on the next. That’s kind of exhausting.

So, if you’ve got a question or a challenge and you’d like to get my help, go to UnderstandingRelationships.com, click the Products tab at the top of your screen on any page, and book a coaching session with yours truly. Until next time, I will talk to you soon.