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20 Most Mismatched Celeb Couples

Niall Horan and Ellie Goulding

Niall Horan and Ellie Goulding

Man, those One Direction boys sure get some mature ladies. Apparently Niall and Ellie were spotted in August 2013 packing on the PDA at a concert in the UK.

Brenda Song and Trace Cyrus

Brenda Song and Trace Cyrus

Yes, Miley Cyrus’ gnarly older brother dated the super innocent-seeming Brenda Song from the Disney Channel.

Britney Spears and Dave Lucado

Britney Spears and Dave Lucado

Britney Spears has been with her normal, non-famous, basic boyfriend David Lucado for the better part of 2013.

50 Cent and Chelsea Handler

50 Cent and Chelsea Handler

A lot of people don’t know that Chelsea and Fitty dated for like, a year! A comedian and a rapper, uh, we’ve seen weirder.

Courtney Stodden and Doug Hutchinson

Courtney Stodden and Doug Hutchinson

It’s not creepy at all that this old guy Doug Hutchinson married this supposedly 18-year-old wannabe Miami housewife when she was only 16.

Mary-Kate Olsen and Olivier Sarkozy

Mary-Kate Olsen and Olivier Sarkozy

Father and daughter or boyfriend and girlfriend? You be the judge.

Hilary Duff and Shia LaBeouf

Hilary Duff and Shia LaBeouf

This was a short-lived romance matched together by the Disney Channel gods.

Sam Taylor-Wood and Aaron Johnson

Sam Taylor-Wood and Aaron Johnson

Besides their 23-year age gap, this odd couple is even weirder than J.Lo and Casper Smart!

Hayden Panettiere and Wladimir Klitschko

Hayden Panettiere and Wladimir Klitschko

It’s like the giant and the princess with these two.

Susan Sarandon and Jonathan Bricklin

Susan Sarandon and Jonathan Bricklin

That’s Susan Sarandon’s boyfriend. He’s about a million years younger than her and they bonded over their love of ping pong. We don’t know what’s weirder, his mustache or his mommy issues.

Mary-Kate Olsen and Heath Ledger

Mary-Kate Olsen and Heath Ledger

After Heath Ledger died, it was revealed that he was having an affair with Mary-Kate Olsen of all people and that she raced to his hotel room after his death. Strange.

Avril Lavigne and Brody Jenner

Avril Lavigne and Brody Jenner

The phony rock star and the phony reality star. Actually, these two fakers made a lot of sense together.

Emma Stone and Kieran Culkin

Emma Stone and Kieran Culkin

Yeah, one of the Culkin’s dated Emma Stone. Random.

Lady Gaga and Taylor Kitsch

Lady Gaga and Taylor Kitsch

We’re not convinced that Lady Gaga isn’t actually part-alien and Taylor Kitsch is just a regular old dude.

Mila Kunis and Macaulay Culkin

Mila Kunis and Macaulay Culkin

Damn, those Culkin bros landed some A-list chicks. Mila and Macaulay dated for nearly a decade.

Cher and Tom Cruise

Cher and Tom Cruise

Yeah, Cher and Tom dated for a minute a long time ago.

Nicole Kidman and Lenny Kravitz

Nicole Kidman and Lenny Kravitz

Lenny just seems too cool and chill to date a fun-suck like Nicole Kidman.

Ashley Olsen and Lance Armstrong

Ashley Olsen and Lance Armstrong

When did this happen? What the heck?

Katy Perry and Russell Brand

Katy Perry and Russell Brand

This pairing was so weird, their marriage didn’t even last a year.

Demi Lovato & Ryan Phillippe

Demi Lovato & Ryan Phillippe

For some strange reason 36-year-old Ryan Phillippe decided to prey upon 18-year-old Demi Lovato and they casually dated for a minute.