It’s hard to believe that Jerry O’Connell and Giuliana Rancic were ever a couple, let alone engaged. But exactly when he split with the E! host and started dating former Spice Girl – and now ex-girlfriend – Geri Halliwell, is unclear.
At one point it seemed that baseball star Alex Rodriguez was making his way through Hollywood’s blondes — within a few short years, the disgraced New York Yankee dated Madonna, Cameron Diaz and Kate Hudson.
It seems that Rihanna has spent the past six years bouncing between singer Chris Brown and rapper Drake. Meanwhile the pop star’s exes can’t decide whether or not they’re friends or enemies fighting for one woman’s attention. At the moment, neither of them are dating Rihanna and they are buddies — but don’t hold your breath because this scenario is always subject to change!
Long before he started making a baby with Eva Mendes, and before he even dated actress Rachel McAdams, Ryan Gosling was hitting the red carpet with Sandra Bullock. The couple had a May-December relationship back in the early 2000s.
Mike Tyson is a strong man who clearly has a taste for feisty women. The former heavyweight champ has dated supermodel Naomi Campbell (who is well known for her temper tantrums) and had a volatile relationship with former wife, Head of the Class actress Robin Givens.
Cameron Diaz has had her fair share of well-known boyfriends, among them Justin Timberlake, Matt Dillon and Jared Leto.
Kelly Preston has been Mrs. John Travolta since 1991, but before that she was romantically linked to George Clooney and Charlie Sheen.
Victoria’s Secret, Sports Illustrated and reality TV are not the only things Heidi Klum and Tyra Banks have in common. Before Heidi was married to her now ex-husband Seal, Tyra dated the British “Crazy” singer.
Janet Jackson is notorious for keeping her romances under wraps. Many years ago she reportedly briefly dated Matthew McConaughey. The Oscar-winning Texan was also Sandra Bullock’s ex-beau, as they worked together on the thriller A Time To Kill.
As Ray J. so eloquently put it in his song “I Hit It First” he dated – and filmed himself having sex with – Kim Kardashian, long before she became Mrs. Kanye West.
What do hunky actor Olivier Martinez and New Kids On The Block singer Danny Wood have in common? Surprisingly, Halle Berry. The Oscar-winning actress is now married to Olivier but many moons ago she dated the boy band star.
She may have secretly pined for Ashton Kutcher when they both filmed That ‘70s Show, but Mila Kunis had to wait a long time to get her man. She is now engaged to, and having a baby with, the actor who was, until recently, still married to Demi Moore.
He’s happily married to Mariah Carey now – and is father to their twins Moroccan and Monroe – but Nick Cannon used to be Christina Milian’s boyfriend. She played his love interest in the 2003 teen flick, Love Don’t Cost a Thing.
When it comes to men there are quite a few celebs that Taylor Swift is never, ever, ever, ever getting back together with. They include - in no particular order - Joe Jonas, Harry Styles, Taylor Lautner, John Mayer, Jake Gyllenhaal and Conor Kennedy. Miss Swift is a very, very, very, very busy girl!
Speaking of John Mayer he's another person who has dipped into the celebrity dating pool multiple times. He can tell his grandchildren that he has dated Katy Perry, Jessica Simpson, Jennifer Aniston and the aforementioned Taylor Swift.
They say Hollywood’s a small town, but when you look at who’s dated who, it proves especially true. A surprising number of celebrities – and high-profile ones, at that – have romanced the same person, sometimes at the same time. Here are a few of our favorites that prove that Tinseltown has a smaller dating pool than you think.