I've thought about this a lot, and here are my thoughts.
First of all, making fun of Dennis Kucinich is about as difficult as beating Christopher Reeves in a game of hopscotch, so I don't think you want to go there.
Second, If you're going to come off as a real liberal "progressive", you can't ask a real question. To come across as a real liberal, you must make a statement of belief as a rhetorical question, and then ask for his agreement.
Third, our goal is to get Bush in the White House, not humiliate a pathetic individual who is running for President and still can't get a date. Therefore, the question is, how do we induce Dennis to take actions that will help our cause? With these considerations in mind, here is the question I suggest you pose to him:
"Sir, despite your progressive and caring politics, it's obvious that the Democratic party has become such a tool of the multinational corporations that they will never support a candidate who truly has a vision for a loving and caring America that will fit into the global community. I believe that you should join forces with Ralph Nader, and run for the Presidency on the ticket with him. It doesn't really matter which of you is on top. In fact, you could have a co-Presidency and take turns. A Kucinich-Nader candidacy could reach out on the college campuses. Willie Nelson, the Dixie Chicks and Madonna would surely do fundraisers for you, and instead of begging for donations, you could have a series of concerts for Peace across this great land. Please do it, Mr. Kucinich. Won't you join forces with Ralph Nader for a really progressive Presidency?"