I started "cold approaching" women last year because I realized it was always something I wanted to do and initially I got a lot of excitement and felt great every time I did it, even when getting rejected. But after over 200 approaches, only one girl has gone out with me again afterward, and it wasn't even a date since nothing actually happened.

I don't think it's my looks as I've had some success in getting dates from Tinder, and recently was briefly dating a really attractive woman from Tinder who showed me so much lust and passion and made me happier and less lonely than I've been in a long time. But she broke it off completely unexpectedly a week ago and it stung. So I've been trying to approach again to move on, but it just isn't as fun anymore and I don't feel any sense of accomplishment from the approach itself anymore. I still do approach, but I find myself missing opportunities because subconsciously (and sometimes even consciously), I assume that it's a million to one chance that some random woman on the street will actually end up interested in me after I butt into her conversation with her friend to hit on her and tell myself it's not worth the effort and anxiety that it will cause me. But then I end up feeling awful afterward anyway. What is the best way to get rid of this jaded and cynical attitude I'm developing about approaching? Any unique ideas or suggestions for new ways to make it exciting or turn it into some kind of game that I could actually enjoy? I think the problem is I'm mostly an introvert and suck at small talk with a complete stranger. I'm actually okay on first dates from online because I feel like the woman has some interest in me already.