Were I debating him on TV, I'd intentionally start pushing his buttons. Not only does Dean lack the charm and savvy to avoid the trap, but he'd come across as creepy and unhinged.
Can you imagine President Dean with nuclear weapons? I think the briefing would go something like this...
Briefing Officer - "As you know, sir, this man has the nuclear launch codes in his suitcase. Every morning the codes are scrambled, and he cannot unscramble them until he sees you take your meds."
Dean - *SNARL, SNARL*
Beiefing Officer - "Correct, sir. He has to see you take them in person. And no hiding them under your tongue like last time"
Keep in mind that nationwide, Dean's approval rating is only 15%. The only places where Dean is really scoring high numbers are in New Hampshire and Iowa, and in Iowa he's still statistically tied for first with Gephardt. Howard the Dean may be the media darling of the moment, but there's no reason one of the other Dwarves can't end up stealing the whole thing from him in then end. Back in 1992, Clinton lost NH big, and barely even registered in Iowa.