When you say, "I try to be a really good listener," what exactly do you figure that means? And I'm also wondering if monologe-ers are simply at nature that way, and no amount of gentle redirection will cure them of their ills. I guess my answer to the OP's question is, it may be a deal-breaker if only because it takes some effort to get past this kind of awkwardness, and if you are not willing to then maybe there is a good reason you are not willing to. Under the circumstances, I feel like I should say, "How interesting. You're building a base of knowledge about the other person upon which you will build subsequent conversations. It's an easy way to get conversation going back and forth without playing 20 questions. You could say something like "It's all too much to take in!
So he feels he needs to lead the conversation?
FOR GUYS: What does it mean when a guy talks too much on a first date?
Stop giving off 'active listening' signals. It could mean he does not like to be interrupted. In this respect, attempt to lead by example. And I should add, to respond to some of the stuff folks have said above, it's definitely not about men vs. Listeners The shy ones me Talkers He's just the type who talks too much. Jump into the conversation and quit leaving these guys doing the heavy lifting.