Cliff. Shag. Marry. I'll start you off: Dean Winchester, Michael Scofield, Sam Winchester.
(The rules: Three names, you've got to toss one off a cliff, shag the second, and marry the third, no exceptions, no matter how difficult or gross; all public figures (IE celebrities, politicians, etc) and all fictional characters are fair game; livejournal users and ex-boyfriends are not; jump into any comment thread you feel like with answers; in your answering comment, include three more people so the game continues; don't worry about spamming me.)