The only thing that we love better than a celebrity is when two celebrities date each other! Back then, all we could do is look in the magazines and on TV celebrity spotlight shows in order to find out who was dating who. Often times, we found ourselves hoping for a great outcome and other times, we wondered what the heck they were thinking! Some of these celebrities were a pretty odd match to begin with and others look like they could’ve worked out. Take a look:
1. Drew Barrymore and Corey Feldman.
These two were pretty epic at the time and so this is no surprise and yet, we have since forgotten that they dated!
2. Heather Graham and James Woods.
Wow, she was pretty young and he’s just creepy old by comparison!
3. John Stamos and Marlee Matlin.
Wow! This is a union we all wanted to forget for sure.
4. Helen Hunt and Matthew Broderick.
Well, this was a cute couple! Why didn’t they work out?
5. Rob Lowe and Winona Ryder.
Why not? They were both gorgeous! I’m sure they both still are.
6. Emilio Estevez and Demi Moore.
Maybe he left her because she dressed like a grandma! Perhaps if she lost the glasses and oversized sweater, they would still be together.
7. Pamela Anderson and Scott Baio.
She should’ve stayed with him because this is the best picture that I have ever seen of her. But I guess she wanted to stand out more.
8. Brad Pitt and Christina Applegate.
They were adorable! Too bad this ended. It looks like they could’ve taken on the world together.
9. Brook Shields and Michael Jackson.
We were all surprised about this union. Well, anyone who dated Michael Jackson back then was really a surprise.
10. Tom Cruise and Cher.
Yeah, this looks like the coolest relationship ever!
