This might seem like an out of place question to ask here, but I'm sure there are folks here on HN who have experienced something like this at some point, and I believe the people who would understand my issues best and would be able to provide actually useful tips can be found here.I possess the typical hacker mindset with interests and passions that are not so "popular". I'm socially awkward and bad at talking, especially so when I don't have much in common with the other person. I don't think I have a good sense of humor and I tend to have a cynical and pessimistic outlook on things, i.e I'm not what one would call a "fun guy".
So I run out of topics to talk about and the conversation quickly becomes boring for both of us, even though we're genuinely interested in each other.Please note: I won't be taking "Find someone else" as an answer.