Tom's been sniffing around Bravo's ladies of the Big Apple since his appearance way back in season one when he flirted with a then-married Ramona Singer and her friends. But it's his resurgence in season eight that's earned him a spot on this list. After his relationship with Luann de Lesseps led to an engagement in record time, we learned that he'd gone on several dates with a now-single Ramona (the number of which he'll contest until he's blue in the face, though he'll still make time to remark about the Singer Stinger's grapefruit scent AT HIS ENGAGEMENT PARTY) and been friends-with-benefits with Sonja Morgan for A DECADE. And then Bethenny Frankel got the damning photographic evidence of his public make-out session with a stranger the night prior to his engagement party, which he denied, then blamed on alcohol and an old friend with predatory clutches, and then tried to explain away by bullying Dorinda Medley into lying for him. What a catch.