I was painfully shy around women
Took me years to get over it. Sad part is I was a good looking guy, I worked out a lot. I had a great career as a NYC investment banker and dressed really well.
I met plenty of women, but never learned how to react to women who made overt advances on me. My brain would shut down and I'd go back to being the fat, shy, awkward kid I was at 12.
I had a smoking hot Hooter's waitress in Palm Beach write her number on the back of my credit card receipt, didn't call her. I had a 22 year old new girl in my group ask for my help on something then she proceeded to rub her t*** against my arm. I had an attractive blonde flight attendant start giving me a neck rub as she asked about a good place for a drink that night in NY. Women I did meet and had s** with were ones I'd meet in a more relaxed setting with friends or that I knew for awhile.
Funny thing is, that I was insane in the hours I worked because I still saw myself as the fat, shy, awkward kid.
Can't change the past but damn did I waste numerous chances.