Hey missatomicbomb, the thing that jumps out from your post to me is this:
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i am a very lonely person. i don't really have friends, and making connections with people beyond the usual small talk is really hard for me, since i'm a super closed person.
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This has been an issue in my life too, and it's something I chose to work on. I can tell you first hand that the way you feel now does not have to be set in stone, the social muscles are like any others, they waste away if you don't exercise them but you can work on them and build them up.
It sounds from what you've written like you really admire this guy who has a good social life, do you think it's possible that this may be indicating you may want to have more of that kind of life yourself?