There are those celebrity couples everyone knows used to date – who could forget Britney Spears and Justin Timberlake – but then there’s some that probably missed your radar.

Whether it’s a one-time fling or a serious relationship, check out some of the unexpected celebrity pairings below.

Mila Kunis and Macaulay Culkin

Before there was Ashton Kutcher and a baby, Kunis dated the actor for eight years before they split in 2011.

Amy Poehler and John Stamos

It may have just been a small fling but the comedian recently told Howard Stern, “We worked on a movie. He did a little bit in a movie that I did and a bunch of us hung out. And then later on he's like, 'Let's go get dinner. And it was fine. I remember thinking like, 'Oh, s--t. Like, if this is really a date…' I think I was wearing a Leslie Knope top. I think I was wearing a shirt from work.”

Ryan Gosling and Sandra Bullock

The Murder By Numvers co-stars briefly dated from 2002-2003 and parted on amicable terms.

Owen Wilson and Kate Hudson

The two actors had an on/off relationship from 2006-2007, and again from 2008-2009.

Alanis Morissette and Ryan Reynolds

The singer and Blake Lively’s husband dated from 2002 until 2007.

Matt Damon and Winona Ryder

The two met in 1997 through Gwyneth Paltrow, who at the time was dating Damon’s best bud, Ben Affleck. They broke up in 2000.

Gwyneth Paltrow and Brad Pitt

Speaking of Paltrow – she was once engaged to Angelina Jolie’s husband in the ‘90s.

Cameron Diaz and Matt Dillon

The There’s Something About Mary co-stars dated from 1995 to 1998.

Tom Cruise and Cher

Yep. These two dates in the ‘80s.

Matthew Broderick and Helen Hunt

Before there was Sarah Jessica Parker, Broderick dated Hunt way back in 1987.

Natalie Portman & Jake Gyllenhaal

These two stars were an ítem in 2006.

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