What am I doing wrong

Posting this under an anonymous account because people I know hang around on reddit.

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Before posting my problem, I'll give you some pertinent details:

• I'm 37, turning 38 in June.
• I recently broke up with my girlfriend of close to 4 years, because we just weren't working out.
• I've only dated 6 or 7 girls in 20 years
• Sex life is non-existent (average gap is 4-6 years). When I was 19 or 20, I had some luck at least meeting girls that led to hookups, but in the last 10-15 years, that's dried up.
• Since 27, I've only dated 2 girls, one for 1 year and one for 4 years.

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The problem: I'll preface this by saying that I'm a nice guy. Not las in..."I'll come over and cat sit while you go out with your boyfriend" nice, but just...gentlemanly. I try to not be a dick to women. The problem that I have is that I've never had "game", never been able to talk to women, and now that I'm getting older (again, turning 38 soon), I'm really starting to worry about my future (want kids).

I went through a long period of depression between 27-early thirties. This was originally brought on partially by PTSD/guilt from things that happened when I was deployed, and partially from my trouble meeting girls. A friend of mine and I used to hang out with this guy who could pull girls at a club every night, but was a huge douchebag and treated them like shit, and seeing him have success when I didn't destroyed my confidence. I had thought about killing myself, even came close to doing it once or twice, but then I met someone and I eventually got over it.

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After I broke up with my ex I went out with a friend and without even trying (or looking), met a girl who was 10 years younger than me. She started talking to me, so i reciprocated, but had a hell of a time figuring out how to get her number. I managed to somehow and we ended up going out 5 or 6 times in 2 1/2 months. Things didn't really progress with her the way most of my past relationships did (at least kissing by the 3rd/4th date), but she had recently got out of a relationship as well and wasn't really looking to jump into a new one right away anyway. I figured we'd take things slow since I wasn't exactly looking, but would still indicate my interest in her. We'd done V-day dinner, and by the time her Birthday came up, I did what I thought would be nice and took her out for a fancy dinner. I had originally planned to take her out to a club and get bottle service, since she and I both like going out, but her friends weren't available at the time, so I agreed that we could go shopping instead (thinking I was going to buy her a new dress or something, since she was always talking about fashion at clubs). Fast forward 2 hours after dinner and I somehow got suckered in to buying her a 2800$ LV bag (in addition to the 560$ dinner), and only got a hug afterward. You don't need to say it, Yes, I got taken advantage of because I was a nice guy.

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I've read tons on the internet, and talked to dozens of people. "Be yourself", "Girls like a guy with confidence", etc. I've heard it all before, dozens of times. The problem is I simply have no clue what to say to girls at every point. I don't know how to approach, what to say, how to read queues, or ask for a number. I don't know when it's ok to kiss a girl, how to ask her back to my place, etc. When I do manage to end up with someone who shows some sort of interest, I either get taken advantage of, or it's with someone I'm not compatible with and ended up settling for because I had no other options.

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Over the last year or two the depression has started to come back. All of the 10 or so friends I have are either in relationships, married, have kids, or live far away. We have solar eclipses more often than I have sex. I've even tried contacting "escorts" just to find an attractive woman to go do things with, but they don't reply. I (and girls I know) would say I'm good looking, not male-model good looking, but not exactly a 4 or below). I have good posture, don't smell, workout, own a home, drive a nice car. If girls were to talk to me, I can hold down a conversation just fine, I just can't initiate or ask for numbers. I really need some sort of help. When I was 18-21 I had a lot better luck...and confidence, but since things started not working out, I think it's all but gone.

​

The point that I'm trying to make (the TL;DR), is that I know I'm generally a nice guy. I like doing things for people, but at the same time, at 37, I have almost zero experience with women. I've been shy my whole life, and wouldn't be able to approach a woman at a bar/club/airport/whatever if my life depended on it (I don't know what to say, or how to close and ask for their number). Recently with the fiasco of buying this girl who won't even kiss me a purse, plus thinking about all my friends who are married and have kids, the depression has started to come back, and it's worrying me. I don't know what to change, or how to get "game" or confidence to where I can be comfortable talking to women I don't know. I've thought about offering money to people who can help me improve my situation and teach me these things, as I have enough disposable income (not flexing), but I'm running out of ideas/ options, and I would like to have kids sometime soon. I had tried using Ecstasy, it definitely helped me approach women at festivals, but I can't take that daily, and that's not a viable long term solution.

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I don't know what to do.

Submitted April 18, 2019 at 03:32AM

Posting this under an anonymous account because people I know hang around on reddit.​Before posting my problem, I'll give you some pertinent details:I'm 37, turning 38 in June.I recently broke up with my girlfriend of close to 4 years, because we just weren't working out.I've only dated 6 or 7 girls in 20 yearsSex life is non-existent (average gap is 4-6 years). When I was 19 or 20, I had some luck at least meeting girls that led to hookups, but in the last 10-15 years, that's dried up.Since 27, I've only dated 2 girls, one for 1 year and one for 4 years.​The problem: I'll preface this by saying that I'm a nice guy. Not las in..."I'll come over and cat sit while you go out with your boyfriend" nice, but just...gentlemanly. I try to not be a dick to women. The problem that I have is that I've never had "game", never been able to talk to women, and now that I'm getting older (again, turning 38 soon), I'm really starting to worry about my future (want kids).I went through a long period of depression between 27-early thirties. This was originally brought on partially by PTSD/guilt from things that happened when I was deployed, and partially from my trouble meeting girls. A friend of mine and I used to hang out with this guy who could pull girls at a club every night, but was a huge douchebag and treated them like shit, and seeing him have success when I didn't destroyed my confidence. I had thought about killing myself, even came close to doing it once or twice, but then I met someone and I eventually got over it.​After I broke up with my ex I went out with a friend and without even trying (or looking), met a girl who was 10 years younger than me. She started talking to me, so i reciprocated, but had a hell of a time figuring out how to get her number. I managed to somehow and we ended up going out 5 or 6 times in 2 1/2 months. Things didn't really progress with her the way most of my past relationships did (at least kissing by the 3rd/4th date), but she had recently got out of a relationship as well and wasn't really looking to jump into a new one right away anyway. I figured we'd take things slow since I wasn't exactly looking, but would still indicate my interest in her. We'd done V-day dinner, and by the time her Birthday came up, I did what I thought would be nice and took her out for a fancy dinner. I had originally planned to take her out to a club and get bottle service, since she and I both like going out, but her friends weren't available at the time, so I agreed that we could go shopping instead (thinking I was going to buy her a new dress or something, since she was always talking about fashion at clubs). Fast forward 2 hours after dinner and I somehow got suckered in to buying her a 2800$ LV bag (in addition to the 560$ dinner), and only got a hug afterward. You don't need to say it, Yes, I got taken advantage of because I was a nice guy.​I've read tons on the internet, and talked to dozens of people. "Be yourself", "Girls like a guy with confidence", etc. I've heard it all before, dozens of times. The problem is I simply have no clue what to say to girls at every point. I don't know how to approach, what to say, how to read queues, or ask for a number. I don't know when it's ok to kiss a girl, how to ask her back to my place, etc. When I do manage to end up with someone who shows some sort of interest, I either get taken advantage of, or it's with someone I'm not compatible with and ended up settling for because I had no other options.​Over the last year or two the depression has started to come back. All of the 10 or so friends I have are either in relationships, married, have kids, or live far away. We have solar eclipses more often than I have sex. I've even tried contacting "escorts" just to find an attractive woman to go do things with, but they don't reply. I (and girls I know) would say I'm good looking, not male-model good looking, but not exactly a 4 or below). I have good posture, don't smell, workout, own a home, drive a nice car. If girls were to talk to me, I can hold down a conversation just fine, I just can't initiate or ask for numbers. I really need some sort of help. When I was 18-21 I had a lot better luck...and confidence, but since things started not working out, I think it's all but gone.​The point that I'm trying to make (the TL;DR), is that I know I'm generally a nice guy. I like doing things for people, but at the same time, at 37, I have almost zero experience with women. I've been shy my whole life, and wouldn't be able to approach a woman at a bar/club/airport/whatever if my life depended on it (I don't know what to say, or how to close and ask for their number). Recently with the fiasco of buying this girl who won't even kiss me a purse, plus thinking about all my friends who are married and have kids, the depression has started to come back, and it's worrying me. I don't know what to change, or how to get "game" or confidence to where I can be comfortable talking to women I don't know. I've thought about offering money to people who can help me improve my situation and teach me these things, as I have enough disposable income (not flexing), but I'm running out of ideas/ options, and I would like to have kids sometime soon. I had tried using Ecstasy, it definitely helped me approach women at festivals, but I can't take that daily, and that's not a viable long term solution.​I don't know what to do.