Hey Brownman,
Firstly, you look pretty good man. You just look like a guy who needs to shed a few pounds (like 90% of the guys out there).
I wouldn't worry about what you look like in bed. My experience is that they are far more worried about what they look like. At 37, trust me, it isn't going to be an issue and while you are not YET a candidate for the cover of Men's Fitness, you have a very normal looking physique. I have a fairly mild/moderate case of gyne, like you, and it has never been an impediment.
In my opinion, you do need a better attitude about it. Don't go into any date with a fixation on getting laid. Just relax and try to have a good time. Focus on having a fun date, nothing more The best part is the chase anyway, so enjoy it. If you are desperate to get laid, guess what? You'll be striking out big time.
Just be confident. Girls are attracted to confident (not cocky) guys, and they can smell a guy that is desperate to get laid a mile away and will get scared off most times. In a group, they always go for the quiet, confident guy - not the yappy, attention seeking guy. Play it cool, have fun, and they will come to you. Give a compliment or two, but don't throw out too many - less is more.
I suppose we will be looking at a model for Men's Fitness in a month! Good Luck. Look forward to seeing your results!
