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
Yes, Miley Cyrus’ gnarly older brother dated the super innocent-seeming Brenda Song from the Disney Channel.
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
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
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
Father and daughter or boyfriend and girlfriend? You be the judge.
Hilary Duff and Shia LaBeouf
This was a short-lived romance matched together by the Disney Channel gods.
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
It’s like the giant and the princess with these two.
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
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
The phony rock star and the phony reality star. Actually, these two fakers made a lot of sense together.
Emma Stone and Kieran Culkin
Yeah, one of the Culkin’s dated Emma Stone. Random.
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
Damn, those Culkin bros landed some A-list chicks. Mila and Macaulay dated for nearly a decade.
Cher and Tom Cruise
Yeah, Cher and Tom dated for a minute a long time ago.
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
When did this happen? What the heck?
Katy Perry and Russell Brand
This pairing was so weird, their marriage didn’t even last a year.
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.