I've been on a self improvement journey for 15 years. I've gone from full social anxiety in HS to party ring leader after college. I'm 35, in great shape, well groomed, good hygiene, well dressed (fitted and stylish), I have a great personality and sense of humor. When I join a friend's group for a party or festival I immediately make friends and become the favorite person in the group. I have a great career, a mortgage on a 3 bed town house near Newport Beach, CA. I work as a technical sales engineer. I'm skilled in snowboarding, wake boarding, skate boarding, etc. Anyone who isn't a half attractive single woman says I'm good looking and shouldn't have any issues meeting women.

Problem is, everytime I approach a single woman, whether in the wild or in a group setting, they never let their guard down. I have approached probably in the thousands now for over a decade. Everytime I walk up as confidently as I can, standing tall, shoulders back, eye contact, smile, etc; and everytime I'm met with a blank stare, reluctance to engage, short/brief/vague answers or just flat out ignored. I usually keep it simple by greeting them, maybe throw a compliment, comment on something relevant, ask questions, invite them to my groups table, make jokes and nothing seems to work. I can't get past a few sentences before they exit the "conversation" or it gets super awkward. No one has been able to explain what I'm doing wrong and just give a blanket coverall statement of just be more confident. This confuses me because I'm usually the only one approaching, dancing, I'm having just as much fun or more as the everyone else in the group. Yet these girls always ditch me for my more conventionally attractive friends who aren't doing anything but standing around.

I'm at a point where I don't know how to improve myself any further. I know you can always keep going but I'm already light years ahead of everyone i know in most areas of my life except maybe conventional beauty standards, which I've mostly already maxed out. I don't know what else I can do more of without completely losing who I am and putting my health at risk.

I've had 3 girlfriends and a few hookups but they have all been unsatisfying and really I was mostly settling due to no better options after extended periods of time. These were mostly pure luck and my GFs I think used me because their previous relationships were abusive and neglected. They treated me like a great, responsible, stable BF but never as someone they were actually attracted to. Never as someone they think is hot or sexy. Just a responsible choice. I ended up breaking up with them because it felt too platonic.

My main issue is getting the conversation past a couple sentences or past the greeting. Hooking their interest quickly and getting them to engage in the conversation. Once I have that the game is easy, but I'm constantly stuck at the starting line except in very rare occasions.

I have several friends who hook up with ease and I've studied them for years. What I learned is we do the exact same thing, but when I say "Hi" I get blank stares and silence. When they say "hi" the girl smile, makes eyes contact, introduces herself and engages the conversation. I'm batting 1/100 and they are 85/100. I'm actually approaching and they stand around until something passes by or approaches them. I don't know what to do.