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Sometimes I meet an interesting girl, and want to start a conversation with her. The problem is that I have trouble holding a conversation. What should I do if I can't hold a conversation with a girl? It's happened with three girls this past semester.

You can always ask her questions. Maybe try to point out something interesting or funny. If it doesn't work just try again. I got a lot of practice at small talk working retail. I pretend I'm Studs Terkel and interviewing people and I try to find out something interesting about them in a short time period. Say you do finally manage to have a good conversation, transitioning from that point to the next is perhaps more difficult than the first part.

Avoid monologues as much as possible. When you think you have anything interesting you like to share, finish it off with a question and leave the ball in her camp. Then think of what possible responses she could give to your question ahead and try to anticipate a possible remark to her response. That way you can keep the conversation interactive and you'll avoid her getting bored with you because you either engage in long monologues or you have too many pauses thinking of a reply or comment.

And like the previous poster also mentioned, humor is a powerful tool when used in flirting. I've seen women literally melt for a man who knew at what time to insert what witty remark (which made me quite jealous). It does require a lot of practice if it doesn't come natural to you, though, and I still fail in that area myself. I really need more practice