THE LOVE NEST: Gramercy Park Hotel, New York City

THE PLAYERS: Lance Armstrong and Ashley Olsen

THE DISH: The third May-December hookup on this list comes courtesy of seven-time Tour de France champ Armstrong and now-legal childhood star and twin minimogul Olsen. Tabloids first got wind of the pair in October 2007 when they were spotted getting very friendly at the Rose Bar in the Gramercy Park Hotel, an Ian Schrager–owned, Julian Schnabel–designed celebrity hot spot. (Star sightings are common at the Gramercy: Jennifer Lopez had her baby shower here, Kate Hudson likes to visit on nights out with pals, and everyone from Lindsay to Anne Hathaway has checked in.) The then 36-year-old Armstrong had cocktails with friends while the 21-year-old Olsen perched on his lap, flirting and, by some accounts, engaging in full-blown make-out sessions. Of course the official response from the stars' camps was to deny, deny, deny—but their denials were somewhat undercut when Olsen was spotted in Austin, Texas, in the following weeks.

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