I'm in a similar boat and I've resolved to keep trying to make some connection with someone. Maybe one day I'll personally know someone enough that I can open up to.
I haven't been in a relationship in a couple years (to say the last one ended badly would be an understatement) and I've never had a close friend just people I sometimes talk to at my University and my job. I'm introverted and kept telling myself I'm ok with being alone but I keep breaking down and crying from the pain of being so lonely.
My solution is to just keep trying. I recently asked a girl out for the first time in years and she said no but it didn't bother me, I'm not lonelier than I already was. Rejection is never as big a deal as we assume.
Also, and I know how clique and cheesy it sounds but, if the guy felt insecure about a girl knowing more than him, he wasn't worth socialising with.