I’ve never been on a date or had a GF. I’m frustrated and confused. Help!

LegoYourEgo asks:

I don’t know how to start this, but I simply don’t know why I have such a difficult time. Whether it’s me having a job, being fit or fat, being active or lazy I still feel the same when it comes to dating. I’m not much of a texter. I’m a great conversationalist though. Many of my friends (women included) see me as extremely intelligent and very friendly.

At this point all I can summarize is my life experience is dramatically different from most people. I’ve traveled and moved around a lot. My career has been all over the place, but very enthralling none the less. I feel like an enigma to most people. I’ve had people who know me for years ask if I was secretly gay because I’m not precocious about women and/or they don’t see me with one. I don’t talk about women I’m interested very much either. Mostly because in the past when that happened a guy will overhear and think to himself “she’s on the market”. I find “kissing and telling” to be violating her privacy

I’ve asked my friends, men and women, what they think and they are always shocked. They respond with how smart and handsome I am and how it shouldn’t be a problem, I should just put myself out there. I have social anxiety but I feel like I’m at a point in my life where that doesn’t affect me as much. I put myself out there a lot and have been told I have balls for some of the things I’ve done. Which confuses me even more because I didn’t think what I was doing was seen as brave.

When I’m attracted to a woman I chat her up, get her number, text a little and ask if she would like to go out on a date. Most of the reactions I get are scorn or just complete awkwardness. Very rarely do I get a polite rejection. Never have I had someone accept it. I’m an open-minded Christian and I’m not into casual sex. I’ve had sex twice with two very kind women, but I found myself having feelings for them and they weren’t in a place to date. What’s funny was I wasn’t even concerned about dating in my early twenties. There were crushes and what not, but the enormity of what I’m dealing with didn’t quite hit me. Anyways I really don’t know what to do. I surf Tinder with my bio explicitly stating I’m not into hook ups and I try my best to interact with women in public or at friendly gatherings. I feel like something else is expected of me when I try to be romantic or put myself out there with women, but what I expect to occur is hardly what happens.

If I knew I would’ve felt this way I would’ve been obsessed about getting laid and what not when I was younger. As damaged as people might be from the casualness they aren’t as concerned and seem to be more aware of themselves. I don’t know if anyone here has experienced this or if anyone has advice. I just don’t know anymore and I feel as I get older the bigger the red flag becomes that I haven’t had a relationship. It makes me sad sometimes and all I want is someone to cherish life with. Thanks for reading.


Demetrius says:

Since you included so much detail, let’s cut to the heart of the matter. Here’s some reasons why you’re having trouble dating and meeting someone new:

  1. You’re too passive
  2. You’re either sensitive, or you’re more obnoxious than you let on
  3. You’re an “open-minded” Christian who doesn’t want hookups but you’re using a dating app for hookups. Also, you think that people who engage in casual sex are “damaged
  4. Your perception of yourself and how your peers perceive you
  5. You are not stable when it comes to your location

I’m not saying you’re a bad guy because of any of those things, I just know that these are your barriers. Let’s briefly talk about each of them and then see what we can do about making dating a more pleasurable experience for you.

First, the passivity. There’s a big difference between being a private person versus coming off as not interested. It sounds to me like you don’t really make your interest clear to the women you’re interested in. It just seems weird to me that you said that in the past when you’ve talked about a woman you’re interested in that a guy will overhear you and think she’s on the market. That makes no sense to me, unless the way you talk about the women you’re attracted to is the way people talk about their friends and not their love interests. If I’m talking about a girl I’m into, it’s very clear that I’m into her romantically and looking to build something with her. It does not, in any way, sound like it’s an invitation for some other dude to step in and try to date her. Maybe your focus on privacy comes off as a lack of interest by both the women you date and the people around you. I’m not saying you need to be a horndog, but that doesn’t mean you have to act like a milquetoast either.

Let’s talk about this whole “scorn or just complete awkwardness” you described when you’re flirting with women. I’ve hit on countless women and yes, I’ve encountered scorn and awkwardness and even derision, but generally speaking I usually get a polite response if I’m being polite. Maybe you’re very sensitive when it comes to rejection, or maybe you aren’t as nice and sweet as you make yourself out to be. A lot of men think that the way they flirt should be universally accepted, even if that flirting is catcalling, and I mean literal catcalling (i.e. psst, psst) or “hey, your body looks attractive, give me your number”. I can’t tell for sure, and it’s entirely possible that you’re just  meeting the worst women ever, but I doubt it. You sort of hint at the fact that you aren’t pursuing a ton of women, so maybe you’ve been rejected 5 times from 21 -26 years old and you’ve magnified the significance of those rejections.

It’s great that you have faith and all, and it’s great that you consider yourself open-minded, but generally speaking, calling people “damaged” for what they choose to do with their reproductive organs is the exact opposite of open-minded. Your opinions are your own, and I wont fault you for having the  sort of mentality that discourages women from sleeping with you, no matter how counterproductive that is. Just know that for the most part, most people your age are a little more open-minded and less judgmental about casual sex and probably wouldn’t call someone damaged because they enjoy casual dating. It’s okay that you want something more serious, but it’s not okay that you’re on Tinder looking for that. There are so many better options for meeting someone for a long-term commitment compared to Tinder, and many of them are free. If you’re a Christian trying to meet a nice wholesome Christian girl to date, why aren’t you meeting women through your church? Or through friends or friends of friends? Tinder is the worst place to meet someone looking for something serious, haven’t you heard? Yes, there are some people looking for more serious connections on Tinder, but they’re not in the majority. It’s a dating app that matches you based on who is nearby.

I think it’s great that your friends think you’re Mr. Wonderful, and that you agree, but a stranger wont know that. You have to  understand that although you are perceived as a great guy, it doesn’t matter to a stranger. My friends think I’m mostly great and definitely a catch, but there are dozens of women who rejected me despite the belief my friend’s beliefs. I know that you were just trying to highlight that you’re a catch and it boggles the mind that you are single, just don’t get too hung up on it. The people who think “I’m a catch, why am I single?” are the ones that generally think that they DESERVE someone great. I think most people deserve to find someone amazing, but belief alone means nothing without actions to back it up. The belief that you deserve someone amazing without the action behind it will only lead to more dissatisfaction.

When it comes right down to it, you don’t seem to be all that stable in terms of where you actually live. I’m sure your career is rewarding to you but if you change where you live fairly often, it’s hard to really connect with someone. It’s not impossible, but it becomes hard to pull off. It’s a barrier, but not an impossible barrier to meeting and connecting with someone.

Now with all your potential dating issues laid bare, how do you overcome them?

  1. Well for starters, you need to work on being less passive. If you like a girl, show her interest and be vocal about it. You don’t have to get into the details of what you’re doing behind closed doors, but make your interest in her known to her. You don’t have to shout it from a mountain top, but you can tell a girl you really like her if you do.
  2. You need to try to avoid getting discouraged by your rejections. Rejections sucks, but there are so many options out there for you. If you’re wondering how to deal with rejection in all it’s forms, you can read about how I overcame my fear of rejection, or listen to the podcast where I cover the topic.
  3. I mentioned it before, but you should either leverage your existing social network (Church, friends of friend) to find a like-minded woman, or join a dating site that is a bit more focused on monogamy. OkCupid lets you choose both your religion and what you’re looking for and you can search by both of those things. Maybe you should start there.
  4. When it comes to how you perceive yourself and how you are perceived, change nothing, but maybe try to focus a little less on it. We all deserve a certain level of respect and happiness, but no one is just going to hand us the things we deserve. Put in the work to prove that you’re as good as you describe.
  5. Finally, your location. Not much you can do about that, other than just be open and honest and acknowledge that it’s a barrier. If you start dating someone, try to call them fairly frequently and even video chat with them while you’re away. That will help maintain any connection you establish and will also help to build a stronger connection.

Okay I’m done buddy. I wish you the best, and I hope that this advice leads you to finding someone to cherish life with.

Good Luck Out There.

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