From Justin Bieber and Selena Gomez (Jelena!) to Britney Spears and Justin Timberlake (Pinky and Stinky!), the MTV Video Music Awards have seen some major, adorably nicknamed celebrity couples cross its red carpet over the years.
Unfortunately for many of these pairs — and the world in general — a lot of these relationships ended soon after they were made VMA-official. But, lucky for us, we have the pictures to prove that their love was once very, very real. So grab the nearest box of Kleenex, and let’s take a look back at the 21 most memorable, fashionable and questionable couples of VMA past.
1. Brad Pitt & Christina Applegate, 1989
This was apparently one of their first, and last, dates.
2. Robert Downey, Jr. & Sarah Jessica Parker, 1990
They were one of the hottest couples of the ’80s, but split in 1991 after seven years of dating.
3. Marilyn Manson & Rose McGowan, 1998
Thank you, relationship gods, for bringing these two together — if only for Rose’s iconic mesh ensemble that will forever be burned into our brains.
4. Tommy Lee & Pamela Anderson, 1999
Well, this was interesting.
5. Diddy & Jennifer Lopez, 2000
Jennifer Lopez (a.k.a. J.Lo a.k.a. Jenny from the Block) and Diddy (a.k.a. Puffy a.k.a. Sean Combs) made a coordinated effort at the VMAs before splitting a few months later.
6. Justin Timberlake & Britney Spears, 2000
It’s pretty much 100 percent certain that these two will never get back together, but hey, can’t a girl dream?
7. Kid Rock & Pamela Anderson, 2001
How did these two not make it work?!
8. 50 Cent & Vivica A. Fox, 2003
This relationship may have been shorter then Vivica’s dress… It’s debatable.
9. Nick Lachey & Jessica Simpson, 2005
They will always be “Newlyweds” to me.
10. Joel Madden & Hilary Duff, 2005
The former Disney princess dated the Good Charlotte rocker for 2 years before they split.
11. Joe Jonas & Taylor Swift, 2008
Shortly before he broke up with her over the phone. Ouch.
12. Katy Perry and Travie McCoy, 2008
Before Katy met Russell, she was hot and then cold (not to mention color-coordinated) with Gym Class Heroes frontman Travie McCoy.
13. Pete Wentz & Ashlee Simpson, 2008
At the time, Pete and Ashlee were proud parents-to-be, but three years later they said their goodbyes.
14. Chris Brown & Rihanna, 2008
These were much simpler times, shortly after they made their relationship public.
15. Benji Madden & Paris Hilton, 2008
Paris just couldn’t make it work with former BFF Nicole Ritchie’s brother-in-law. The two broke up after nine months.
16. Kanye West & Amber Rose, 2009
The couple dated for two years, but had a nasty split. However, Kanye moved on with Kim and Amber moved on with Wiz and both are happy with babies.
17. Russell Brand & Katy Perry, 2011
Their relationship may have begun at the VMAs, but it ended in a not-so-nice divorce.
18. Justin Bieber & Selena Gomez, 2011
The on-again, off-again couple were definitely on (and adorable!) in 2011. Long live Jelena.
19. Jason Trawick & Britney Spears, 2011
Jason and Brit looked so happy at the VMAs, but they called off their engagement in 2013.
20. Niall Horan & Katy Perry, 2012
We know they were never a couple, but they were VMA official for about, like, three seconds so whatever.
21. Robin Thicke & Paula Patton, 2013
A lot can change in a year, huh?