Haven't given up, but i am usually doubtful about most opportunities, however small. I had a much easier time asking female friends out on dates that i'd known through something like sports, education, hobby groups. That stopped around 5 years ago after quite a few attempts that didn't work out. Out of 5 of those dates, 4 of those girls ended up with the guy they truly wanted to go out with, but were just happy to go on a date because they liked me, but maybe i wasn't considered boyfriend material, who knows.
The last 5 years it went from me happy to ask out on dates to feeling lucky if i simply felt a hint of spark or connection or just a little bit of flirting and seeing that as a major success. So things have really gone down hill, and now i can't imagine asking anyone out. Because most of the girls i've ever known, friends, acquenatences, people, tend to go for the guy who is the complete package, or to an extent. I won't say superficial, but certainly, they seem to like the status quo.
But i still hold out that one day i'll meet my destined future girlfriend. somehow.
For some reason from the early 2000s to the mid 2000s i was way more willing to try initiating friendships and dates, but i think because those attempts didn't lead to long term relationships, it really startled me a bit, so now i just wait for it to happen without me doing the work, which hasn't worked..
I think knowing that i've had dates before, and brief relationships, somehow gives me a glimpse that it can be done. But i still find it very difficult.