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When you're talking with someone, 'specially with one for whom you care, and the conversation just degenerates into stuff that doesn't really matter and feels awkward and isn't at all satisfying. Like the Simon and Garfunkel song.

I have this female friend that I talk to occasionally, and every time we talk our conversations end up being about weird, sexual stuff.

Does that count?

I personally enjoy shooting the breeze with people I know. If a conversation with someone you know gets awkward its likely because there's something you want to say or something you want to ask. Say what you have to say, ask what you have to ask and you'll find that these moments with a friend will slingshot from awkward to enjoyable and satisfying.

Ditto, Vapor. Though it is a known fact that men get much less articulate when talking with women they find attractive or they have a huge emotional investment in, especially early on in the friendship. In terms of just regular chats with either non-female friends or female friends you don't consider viable, if they get awkward it's likely for the reasons Stuman listed, or just because there isn't anything really uber-important to say.

I have this problem quite a bit, regardless of who it is. Often times I start rambling and eventually lose the conversation, then crash somewhere off-road where I'm discussing about metaphysical reality things while everyone else has fallen asleep.

^That sounds a lot like me.

"lol" and "k" are conversation cancers. And the people who send just those know it.

The international sign of "this conversation is over" is to repeat back what the previous person said.

^Agreed, that is so annoying. Which is why I had a very hard time believing the professor who was trying to tell me that repeating things back is supposed to be a method of "receptive listening".

And remember, "I'm-a Luigi, number one!"