- Lisa Kudrow and Conan O'Brien: TheFriends actress recently revealed that she dated the late night host before she hit the big time, but they were better off as friends.
- Michelle Williams and Jeremy Jackson: The former Baywatch star (and currentCelebrity Rehab participant) told Howard Stern he had a fling with Williams, who starred in an episode of Baywatch before being cast on Dawson's Creek.
- Tila Tequila and Billy Corgan: Smashing Pumpkins fans wept when these two showed up together at an awards show.
- Christina Applegate and Brad Pitt: This should satisfy Team Jen: Applegate took Pitt to an awards show in 1989 ... then left with another guy.
- Keanu Reeves and Diane Keaton: See, dating someone 19 years younger isn't just for men!
- Amanda Bynes and Seth MacFarlane: OK, theFamily Guy creator and former child star might be the oddest odd couple on this list. They most likely met when Bynes guest-starred on Family Guy.
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