NFL superstar Tom Brady dated several high-profile women before marrying his wife, former supermodel Gisele Bündchen. His list of exes includes Playboy Playmate Layla Roberts, whom Brady dated in 2002, but by 2004, they'd broken up, and Roberts married AltaVista founder John Hilinski.

Interestingly, Brady could've dated former "first daughter" Ivanka Trump with her father Donald's blessing, if the ex-president's words are to be believed. Donald has been a "good friend" of Brady's for a while, and Trump once told Howard Stern that "[Brady] and Ivanka would make a great combination."

As for Gisele Bündchen, it was love at first sight when she met Brady in 2006, but he may still have been in a relationship with his Bridget Moynahan — while she was pregnant. Moynahan had Brady's child in 2007, mere months after he began dating Bündchen, but the two exes have a decent relationship nowadays.