First of all, don't be afraid asking what you perceive to be dumb questions. There are people here or in any other forum such as this one that are willing to help.

Im.assuming you're reffering to friends you rarely see. A "hey, its been a while, wanna catch up" usually works. If it's not just the reaching out aspect that's anxiety inducing, but also when you meetup. What I do is just ask what they've been up to from the last time we saw each other until now.

Also, if you want to discover people that are interested in things you like. Maybe a friend/dating app could help?

i don't see anything wrong with possibly developing romantic feelings with people you know well. While that could bring pain, is it worth depriving yourself of any close relationships? And i get the sense this has happened to you before. If so, how did you cope?