I have the same problem. I find it's nice to have an activity or something going on in the background that can fill in the gaps in conversation. Have a sitcom rerun in the background, listen to a cool album, go for a walk, suggest going mini-golfing, biking, bowling, something light and fun. Not only do these activities/environments stimulate conversation (sometimes a little bigger than smalltalk), but they also fill in the voids that are otherwise awkward for one or both of you.

Then again, maybe there just aren't many people who can carry on a conversation at the level you'd like them to be carried. It's natural to have people around you that you can have a pleasant conversation with, but don't necessarily talk about anything meaningful -- this happens a lot when you've got peculiar interests. That's okay. Sometimes when you really hope you can get to know someone better, it just doesn't happen. Doesn't "click." That's okay too, even though it sucks a bit.

Someone else suggested making small talk to service clerks and stuff. That might be a good idea! I work in customer service and am always friendly with customers who are friendly with me. It IS a skill, socialization -- little stuff like this will sharpen your skills, gives your more confidence. It did for me, anyway. :jointsmile: