So yesterday was the last day before the 2 week holiday vacation at school, and I spoke to this guy I've been friendly with over the year. We've been having trouble talking to each other quite often because I have trouble socializing, but he's noticed me being more open these last few weeks with him and other people.
I apologized for being hard to put up with and told him I have trouble socializing, and he accepted and was cool about it. He said he noticed me being more open and said I should talk more because graphic designers need to open up (we're in vocational training in a graphic design course). Then I let him know that I have nothing planned over the holidays and asked if I could join him on anything. He said he wasn't sure cuz he would be busy working, but we exchanged e-mails.
I'm thinking about asking him if he's going to any New Years Eve party, if he is he's probably going to be around his group of friends and I just wonder that if I ask him if I could join and I end up coming, will he be worried if I don't socialize much and maybe his friends will wonder why I'm there barely talking, maybe making myself and even him embarassed that he invited me? I'm actually trying to fix this problem by talking more at home too with my family, and maybe even watch some comedy movies so I can easily laugh naturally.
Guys here, would you be iffy about inviting me out somewhere with a group of friends? Would you actually let me know that? What do you guys think?
IMHO you offered, the next social move is on his part. I'd wait it out.
If you keep asking IMO you'll come across as overly eager, pushy, desperate or even weird.