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22 Famous Couples That Will Make You Say "I Am Genuinely Shocked They Ever Dated"

I would read a 500 page book about John Mayer's dating history.

1. First and foremost, Alanis Morissette and Ryan Reynolds.

Kevin Winter / Getty Images

2. The iconic Ryan Gosling and Sandy Bullock.

Francois Guillot / AFP / Getty Images

3. Kenny Chesney and Renée Zellweger's very random and very short wedding on some beach somewhere.

People Magazine

4. Shia Labeouf and Rihanna's single date.

In 2007, they went on one date but Shia said: "The spark wasn't there. We weren't passionate about each other in that way, so we remain friends."

5. Matthew McConaughey "shirtless, carrying his shoes, and whistling" after spending the night at Janet Jackson's house.


According to Star Magazine via Popdirt that happened in 2002, so that's that.

6. Then there was Mila Kunis and Macaulay Culkin.

Ethan Miller / Getty Images

7. Hilary Duff and Joel Madden.

Evan Agostini / Getty Images

Always in my thoughts.

8. John Mayer and Jennifer Aniston.

Alberto E. Rodriguez / Getty Images

9. John Mayer and Jessica Simpson.

Matt Baron / Matt Baron/BEI/REX/Shutterstock

10. Honestly, John Mayer's entire dating history is pretty good.

Dimitrios Kambouris

11. Carson Daly and Tara Reid.

Nick Elgar / Getty Images

12. Carson Daly, his dad's suit, and Jennifer Love Hewitt.

Dan Callister / Getty Images

13. Cameron Diaz and Justin Timberlake.

Miguel Villagran / Getty Images

14. Cameron Diaz and Diddy.

Alex Berliner / Alex Berliner/BEI/REX/Shutterstock

15. Avril Lavigne and Brody Jenner.

Ilya S. Savenok / Getty Images

No offense but "lol" and "iconic!"

16. Jennifer Lawrence and Chris Martin from Coldplay.

Isaac Brekken / Getty Images


Isaac Brekken

17. Literally any picture of Jennifer Lopez and Ben Affleck, but especially this one of them sucking face*.

Richard Young / Richard Young/REX/Shutterstock

*SORRY for that graphic descriptor.

18. Ashanti and Nelly.

Kevin Winter / Getty Images

Because it should have been Ja Rule (because they had like 7 songs together, duh).

19. Meghan Trainor and the kid from "Spy Kids."

And how they're having, and I quote, "really fucking great sex." Honestly good for them.

20. Lance Bass and Danielle Fishel.

Lance's Twitter

What a photo, TBH. What a photo!

21. Billy Corgan and Tila Tequila.

Alberto E. Rodriguez / Getty Images

22. And, just like...this:


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