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I've had this issue too. If your conversation box is full OR if the person you're starting a conversation with's box is full, then you can't start a conversation. I think the basic membership level is about 10 or something. A tiny message will pop up if this is problem.
So.....if it's you, then open up all conversations (bottom choice of drop down box), click on several old ones, then select "leave conversation". That will clear some room in your conversation box.
If it's the other person, you have to put a message in the regular post you're trying to respond to them about...maybe "quote" them so they get an alert, and say "I want to start a conversation, so please clear your conversation box"