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This is going to be a very long story so I'll try to make it as short as possible
I was 250 Lbs back in high school and it absolutely annihilated my confidence with women (I was also a huge loser). I didn't lose my V card until the age of 22...didn't even kiss a girl until 22. The damage being a fat loser to my confidence was so bad that even losing all the weight and being pretty good looking after high school couldn't solve my problems. My confidence has improved a ton since those days but it's good to know the start of the problems
As things stand now, I'm 5'10 185...very athletic build (probably 12-13% body fat). I'm a good looking guy in the face, dress very nice, etc... At work I started making six figures at the age of 24, made over 150K last year, have my own house, etc... My lifestyle is totally awesome - my best friend is rich as hell and i obviously do well so we go to all sorts of fun parties, clubs, bars, restaurants, concerts, sports events, etc... I vacation 4 times a year. The rest of my life is pretty much perfect outside of dating. I'm very grateful to be in position I'm in. I'm a good guy outside of the superficial stuff - I treat people well without being a bitch, I can hold a decent conversation, I'm easy to get along with. I have nothing to feel reserved about.
On the dating side, I've slept with about 8-10 women - all way way below my league. The only 2 attractive ones in that group were over the age of 40. None of them were dateable. It's just absolutely terrible. I've never been with an attractive woman my age range. At this point, the vast majority of women are very nice to me but my approach anxiety is intense. I'm equally scared of success as I am of failure. I've suffered tremendously in the past due to being perma-single and it's almost like a torture victim so used to being miserable that they're afraid to leave their kidnapper.
What would you guys recommend for someone like me? I want to meet someone very badly. How can I overcome my fear of success and rejection? Is online dating a good option for me knowing that I look pretty good and my success level?
It's worth noting when I actually get dates, I'm very very good. I've been out on dates with 11 women in my life and 8 of them were VERY heavily into me. Of the 3 that were not, if I got another chance with them now, I would probably close the deal with all of them. I screwed it up by being young and dumb. For the most part, when I get an opportunity I don't mess it up but I rarely get the opportunity because of my anxiety in escalating with women and the naturally passive nature of women. I've had very good looking gay men ask me out so I know i'm not a bad catch. When I'm on a date, I sell myself pretty well (I drive a very beautiful car, dress nice, can make women feel comfortable, my back story is interesting, etc...). I just need a way to get some dates!
If you have money, use it to gradually build up your confidence with hot women. Hire a part time hot woman as your personal assistant to help you with a feasibility study in setting up a business. Meet up in places where there are lots of hot women. Hot women will approach you when they see you with a hot woman. The immersion in hot women will do a lot for your confidence.
As for escalation, nothing beats practice. Take it gradually until you're very comfortable escalating.
You can pm me so I can help you with a Trello task board on the things that you should knockout on a gradual basis. If you want a quicker pace, we can set up another task board for the purpose. Get busy on the tasks and you'll be where you want to be in the shortest possible time.
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Approach. Open. Escalate. Isolate
Here are my two essential rules on texting that will save you tons of time and money:
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