After a painful divorce about 3 years ago, i spent the first 10 months as an emotional mess, and i was not ready to date at the time, nor did i have any ‘game’ or confidence at the time even if i wanted to. Right then i befriended a girl, a very attractive, professional, independant woman. We would go to movies and dinners regularly, just for fun, no romance or anything. Not even ANY innocent flirting ever. At the time i could come off as needy or just very ‘unsmooth’, but even though her friends would tell her unflattering things about me, even things that came across as creepy to them, she stood by me as a friend because she knew i just needed time to get on my feet and over the breakup.
Two years later now….i am totally over the split, i LOVE life, i have gotten myself into top shape, i got my game back, and i never have any problems getting dates or going out or attracting woman, and my confidence is at an alltime high. I’ve been loving the single life the last year and all the freedom and benefits it provides.
But that one friend is the one i have my eye on lately, and she is the only one i can’t seem to get. Perhaps it is because we are friends, and she knew me as the needy emotional mess from way earlier, even though i am a completly different person now. Don’t have a second chance to change a first impression i guess, because it would be totally different if i met her today.
We still go out maybe every couple of weeks or so for sushi or a movie, but last week i gently hinted to her that i think she is very attractive, and now we do little ‘flirty’ things like touch each others hands, or resting my fingers on her knee when we sit at a bar, but it is just innocent and more playful than anything romantic. She once gently removed my hand from her hip at one point, but that didnt spoil the mood or anything, but it did confuse me, because about 10 minutes after she hinted she would love to come on my business trip with me to chicago for fun next week. But i dont think she means for it to be any more than that. i dont want to read anything into it.
How can i gently try to push it just a step further without having it ruin the friendship potentially. She knows that i am popular with women, and have been out on many dates over the last year. Maybe she thinks i am a player, but I would like her to somehow know that she is not like all the others to me. There is a much more genuine connection for me with her, and i would be willing to be much more serious for her.
So how to build a bridge from good friend to girlfriend?




