I have a natural DGAF personality. Not just with women, I just tend to be pretty chill in most situations. But when I get close to closing, I have a very hard time.

It hit me the other day as I was chatting up a colleague. She was cute, but not really my type, and in a LTR. I saw her mostly as exercise for my recent learnings around here. Anyway, good start, I DGAF.

That attitude pays off, and I find myself in a situation where I'm pretty confident I can at least K-close if I start to escalate. But not confident enough. I start thinking about all the problems: we're not entirely isolated, what if ASD kicks in because of that? What if I get caught trying to kiss a taken colleague in front of other colleagues. What if I do close, and office drama ensues? What if, what if, what if. If feel like I was just looking for excuses not to try, because I myself couldn't handle the rejection.

Looking back, I've always had this problem. One of my favorite "moves" pre-TRP was to crash on a girls bed after a party. It was easy to play as drunken fun if she kicked me out, but if she let me in her bed, closing was 100%. It actually worked every time I tried (3 times), which makes it worse because it means I could have closed like a man each time instead of doing such a stupid trick, I read the attraction correctly.

So, what are good ways to learn to handle rejection, and DGAF until the very end?