Strangest Celebrity Couplings


They say love is blind. That’s certainly true for these mismatched pairs. From alleged hookups to whirlwind marriages, these are some seriously weird celebrity couples.

Janet Jackson and Matthew McConaughey

Did they or didn’t they? Rumor has it that these two met at the 2002 Grammys and went back to her place afterward. Matthew McConaughey did confirm that they’ve met and that he considers her to be a “sweet lady.”

Cher and Tom Cruise

While these two have both racked up a couple of high-profile divorces, we never would have guessed that Cher and Tom Cruise ever dated. But she confirmed that they were briefly a couple in the 80s.

In fact, Cher said that he was one of her top 5 lovers. TMI, Cher!

Shia Labeouf and Rihanna

How were Shia and Rihanna ever in the same room together, let alone on a date? He confessed that they only went out once, but that the “spark” wasn’t there. Shia said something similar about his one date with Hilary Duff.

Honestly, dude, it might be you and not them.

Matthew Morrison and Lea Michele

It’s not their fault they’d later play teacher and student. After all, Matthew is just 8 years old than Lea. It’s not like he’s her dad. Still, the fact that these two dated briefly while co-starring on Broadway is just too weird.

Justin Timberlake and Fergie

Do you remember that JTT and Fergie-Ferg were a couple once upon a time? They’re hoping you forget! Fergie told Andy Cohen that it wasn’t a serious relationship and refused to dish about their brief romance.

Ryan Gosling and Sandra Bullock

Back in 2002, a fresh-faced Ryan Gosling fell in love with his costar. No, not Rachel McAdams. That happened later. The leading lady in question was Sandra Bullock, who is 16 years older than Ryan. Despite the age difference, they dated for almost 2 years.

Benji Madden and Cameron Diaz

I always forget that these two are happily married. Ever since Cameron retired from acting, she seems content to enjoy life out of the spotlight. Equally weird is that Benji’s twin brother, Joel, is married to Nicole Richie.

Moby and Natalie Portman

In 2001, the actress and musician briefly dated. This was right after she starred as Queen Amidala in the first Star Wars prequel, and Moby claims that he was “the target of a lot of nerd wrath.”

Maybe the two of them bonded over being vegan? That’s literally the only thing I can imagine the pair having in common.

Madonna and Dennis Rodman.

At first, this couple makes zero sense. You could get a better pairing by drawing two names out of a hat. But first, you have to remember that this was the 90s, when the world was full of strange possibilities.

And then you have to remember that Madonna and Dennis are both free spirits who crave attention. I mean, she also dated Vanilla Ice!

Billy Corgan and Jessica Simpson

The man himself said this was true. Otherwise, I’d never believe it! Billy Corgan told Howard Stern that he “sort of kind of went out” with Jessica Simpson many years ago.

That sounds like a very middle school attitude, Billy. He also went to the 2009 Bravo A-List Awards with Tila Tequila as his date, so who knows what his type might be?

Michael Keaton and Courtenay Cox

Despite a 13-year age difference, this weird celebrity couple lasted a surprisingly long time. Courtenay and Michael dated for six years before splitting up in 1995.

Matthew Perry and Lizzy Caplan

Courtenay Cox’s Friends costar Matthew Perry also enjoyed a bizarre long-term romance. He dated Mean Girls star Lizzy Caplan for 6 years, but they broke up in 2006 after he failed to propose.

Julia Roberts and Lyle Lovett

The weirdest celebrity couple of the 90s might just have been Julia Roberts and Lyle Lovett. They married in 1993, just two years after she left Kiefer Sutherland at the altar to run off with his best friend, fellow actor Jason Patric.

She was America’s sweetheart. He was a country singer known for his… let’s say “quirky” looks. It made no sense on paper, and less than 2 years later, they called it quits.