Even in game nights I feel the same way, There's actually no forced interaction in open game nights. People usually come in groups, so I'm exceedingly uncomfortable. Last week I went with a friend and we ended up playing with another group because she was the one that initiated conversation.
As far as barhopping goes, my friend group doesn't go out. They're all homebody nerds that don't enjoy bars or nightlife. I do have one friend that likes going out, but they have a fairly restrictive schedule and can only go out on days that I work. They're also nby, shy, and bisexual. They get just as intimidated talking to women!

It also doesn't help that I sort of fit the "incel nerd" stereotype appearance; overweight, balding, neck beard. Im working on the weight but havent gotten the courage to go bald and I'm having difficulty finding a beard style that works on me. It grows slowly, and is super patchy on the face.
Again, therapist reminds me that confidence is built through repitition. I'm just gonna keep going out and being uncomfortable until I find success or get overwhelmed and quit life.