Man, I feel your pain. I spent a large portion of my life feeling just like that, including a hell of a lot of time when I should have been interacting with all the interesting/attractive people around me, but just felt like I couldn't connect and couldn't figure out why not. The main things that helped me improve that part of my life have been: -Figure out what I want to do and then do it, stop wasting time on stupid crap like video games or watching/collecting movies and music etc. I'm not saying to cut everything that's socially fruitless out of your life, but figure out if you are wasting a lot of time on things that accomplish basically nothing toward social goals. Also, if you are doing work or study toward stuff that mostly doesn't interest you, your soul is being crushed and your social life will suffer. Then use that time to... -Become interested in other people. I decided to try to become the Zen master of awkward conversation. I found a friendly place, where people talk to each other, to hang out consistently and then would take any opening to try to make a conversation continue. People do want to talk to you, especially if you seem smart* (but not trying to prove it) and interested. They also want to talk about the things they have on their mind. Your job is to ask open ended questions to provoke them into talking, and then pay attention, and feed back some of what you just learned, and maybe a short bit of personal experience on the subject, and continue. I have met a ton of interesting people and learned that most of the people around me that I assumed were boring and vapid were actually mostly kind of shy (even if they appeared social) and just needed to feel like someone was actually paying attention before they would bother to open up and share anything they actually cared about. The things that people actually care about are usually interesting, but most people give up on talking about them to random people, because most people don't actually care what the other person is saying, they just wait for their turn to talk. Sometimes I find myself talking to this type of person, and though it was somewhat annoying at first, I have decided it is part of my giving back to humanity to humor them and let them talk about what they want to talk about. I know exactly what it is like to talk to only one or two people, always the same one or two, every day for months on end, and feel like you are dying to get out whatever it is that's been running through your head. So I let people do that, and I prompt them to continue, and usually, once they get through that, the conversation becomes somewhat give and take again. The thing is to get someone you're talking to to trust that you will not just leave once you realize they are boring, which is everyone's fear. Once they believe that about you, they will also be interested in you, maybe just for the fact that you're the only one they've met that ever gave them the time to talk about whatever. -Don't give up. It may take a long time before you are able to randomly knock up a conversation. And there are a lot of environments that are somewhat hostile to that sort of thing (until, I assume, you are a master.) Go around to all the cafes, bars, etc around you and find one where people seem to be talking to each other more than watching TV (find one without a TV, ugh) or sitting off in isolated groups. It will be much harder to get started in one of those types of places, and the people who will talk to you right off may be on the lonelier/more annoying side of the spectrum. -Don't always assume it's you that's making the conversation awkward. Some people are shier (shyer?) than you are, or are pissed off people, or really have nothing to say. Don't be afraid to try them another time, but don't assume that you've done something to warrant their behavior. They may be having a bad day, or not feel like talking, or just congenitally look pissed off. Assume that, if you are putting in a good faith effort to be friendly and interested, then their reaction is not your personal fault. Just tonight I was explaining to someone that a certain mutual acquaintance probably didn't actually hate him... she just always looks pissed. I was joking back and forth with her the other night, she seemed happy and was laughing etc., but... still looked pissed. Her face is just like that. I don't want to go on and on because I am definitely not the Zen master of conversation, but my point is that if you can make yourself be interested in other people, parse their input to find questions you can ask them to continue the conversation, and then remember what they said and prompt them the next time you see them, you will suddenly find you've made a bunch of friends, or at least (at first) people you can interact with and learn from. If you need to write down who you met and what you talked about and learned about the people, then do it. I was reflecting on things the other night and randomly decided to write down all the people I've met in the last 6 months or so, and whom I could tell anyone a fair bit about, and the total was around 60. This is completely unprecedented in my life (which is sad, but better late than never), and it's only the result of a concerted effort, but one which has been very enjoyable. And at this point, the discomfort and forced-ness of conversation with random people is almost gone, to the point where I sometimes feel like I'm one of those people that used to annoy the hell out of me, who would just start talking to the checkstand girl about whatever, and leave her smiling. I now realize those people are not all putting on a front and acting fake-nice to feel better about themselves or try to get laid - some of them actually do just find other people interesting, and anyone can do that. *an interesting (to me) aside: when I used to try to avoid "using big words" and "acting smart" around people, assuming they would think I was a pompous jackass, I never got very interesting conversation. When I started treating everyone as if they were at least as smart as me, and would understand what I was talking about (barring tech-speak, which I always explain in regular English if possible, or avoid) - I was pleasantly surprised to learn that most people are much smarter than they care to admit, and feeling like they are taken to be smart, and then having the chance to demonstrate it, inspires them to be smarter in conversation. I think a great deal of human intelligence is wasted because people fear the reaction of others if they "act smart".