Before Josh, there was Justin. Before Jessica, there was Fergie. These two dated in 1996. She was 23. He was 16.. Yeah, we’re thinking the same thing.

In 1994, Brad Pitt and Thandie Newton hooked up on the set of Interview With A Vampire and were together for a year. Who knew?

Image by PublicDomainPictures from Pixabay

Edward Norton and Courtney Love dated for three years in the '90s after co-starring in "The People vs. Larry Flynt" together. They were even rumored to be engaged. Things that make you go ‘hmmm’.

Aston Kutcher and Mad Men actress, January Jones were in a serious relationship from 1998-2001. She told GQ magazine how he discouraging her about her acting is how it ended, “He was like, I don’t think you’re going to be good at this. So—f*** you! He only has nice things to say now—if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.” How do you like them apples, Ashton!

Jake Gyllenhaal and Natalie Portman dated in 2006. If you’ve ever seen their last movie together, ‘Brothers’, you somehow feel the intense chemistry of unfinished business.

Owen Wilson and Sheryl Crow dated in 1999 after starring in The Minus Man together. PDA and all..interesting.