I am acquaintances with somebody who is painfully awkward in social situations and has difficulty with boundaries, especially when asking about personal matters. They consider me one of their best friends (even though I've only known them for a few months), but the whole situation is making me feel uncomfortable. I've tried bringing it up in conversation, but I don't want to hurt their feelings. I'd like to be their friend, but right now I feel obligated to be with them because I feel sorry for them. What should I do?
Just like in romantic relationships, we all have different ways of getting to know one another in friendships. Your “awkward” friend simply goes at a different speed than you and has way less qualms about personal comfort zones and over-sharing.
It’s more than alright to be somewhat uncomfortable about this. What’s not alright is to dwell on it so much. You are wasting precious time and energy going on and on about how “awkward” this person is, instead of investing it in actually getting to know them. In fact, I’m inclined to believe that it’s you, not your friend, who is making the “awkwardness” levels go through the roof.
Clearly, this person saw something in you that made them think you could be a great friend. Is Lisa or John a tad overzealous? Yes. But you are more than making up for it with your over-analysing. Stop feeling sorry them, and maybe try to get to know them for who they really are, and not as some manifestation of a word that everybody uses too much anyway.