All the MTV Video Music Award Couples You Wish Were Still a Thing

Prepare to open a Pandora's box of award show history

By Samantha Schnurr, Lena Grossman Aug 17, 2018 12:00 PMTags

The MTV Video Music Awards are the perfect place to debut new music videos, songs and even significant others. 

As the annual award show gears up for its 34th ceremony on Monday night, there's plenty of jaw-dropping history to accompany MTV's signature show. Whether it be Madonna writhing around as a sexy bride in 1984 or the pop icon making an equal splash nearly a decade later with a three-way kiss featuring Britney Spears and Christina Aguilera, the MTV stage has been the designated place for celebrities' musical shenanigans for more than 30 years. Lest we forget the Miley Cyrus' twerking incident or Kanye West's notorious Taylor Swift interruption ("Imma let you finish")?

However, before the show even begins, stars make just as much of a statement when they hit the red carpet—many with a significant other. While some of those celebrity couplings seemed commonplace at the time, some red carpet duos feel like pure figments of our imaginations today. 

MTV VMAs: The Most Memorable Moments of All Time

From former king and queen of pop Justin Timberlake and Britney Spears to Hollywood's bonafide newlyweds, Jessica Simpson and Nick Lachey, prepare to open a Pandora's box of MTV VMA romantic history and long for the good ol' days. 

Ready, get set—go!

Justin Timberlake & Britney Spears

While they didn't wear their iconic denim outfits, the pop world's then-reigning king and queen did delight fans regardless with their joint appearance at the 2000 MTV VMAs.

Jennifer Lopez & Sean "Diddy" Combs

J.Lo rocking a bandanna at the 2000 MTV VMAs—need we say more?

Selena Gomez & Justin Bieber

We would be bad liars if we said we didn't miss this couple just a bit...they broke up in late 2017 after dating on and off for about six years. Here they are at the 2011 MTV VMAs.

Riff Raff & Katy Perry

Speaking of denim, looks like these two paid homage to Britney and JT at the 2014 MTV VMAs.

Ariana Grande & Pete Davidson

A couple of months before they ended their whirlwind relationship and engagement, the pop star and Saturday Night Live performer made their red carpet couple's debut at the 2018 MTV VMAs.

Pete Davidson & Cazzie David

The SNL star and Larry David's daughter dated for two years before splitting in 2018. They attended the 2017 MTV VMAs together.

Noah Cyrus & Lil Xan

Miley Cyrus' little sister and the rapper made their red carpet debut as a couple at the 2018 MTV VMAs, weeks after they began dating...and weeks before they broke up.

Taylor Swift & Joe Jonas

Their's was a short-lived love story; the two dated for three months until October 2008. During that time, they squeezed in an MTV VMAs date, where they were also joined by his brothers and Jonas Brothers band mates, Nick Jonas and Kevin Jonas.

Jessica Simpson & Nick Lachey

The then-spouses hit the 2004 MTV VMA red carpet—pearly smiles and all. They also attended the 2005 show together before calling it quits a year later.

Marilyn Manson & Rose McGowan

The singer's then-fiancée's iconic dress at the 1998 MTV VMAs was apparently a "political statement" against Harvey Weinstein.

Kristen Stewart & Michael Angarano

A year before she dated her Twilight co-star and now-ex Robert Pattinson, KStew was in a relationship with her Speak co-star. They attended the 2008 MTV VMAs together.

Amber Rose & Wiz Khalifa

The model and the rapper attended the 2014 MTV VMAs together, a month before she filed for divorce.

Kanye West & Alexis Phifer

In 2006, years before he married Kim Kardashian, Kanye was engaged to the fellow fashion designer. They attended the 2007 MTV VMAs and ended their six-year relationship the following year.

Nick Jonas & Olivia Culpo

The two broke up in 2015 after two years together. During their relationship, they attended the 2014 MTV VMAs.

Iggy Azalea & Nick Young

The rapper and her then-beau attended the 2014 MTV VMAs. They got engaged a year later and split in 2016.

Eva Longoria & Nelly

It's getting "Hot In Herre" on the red is unclear if the two stars actually dated, but they did look cozy at the 2005 MTV VMAs.

Kanye West & Amber Rose

Here they are at the 2009 MTV VMAs, a year before they ended their two-year relationship. This was also the night 'Ye took the mic out of Taylor Swift's hand...

Kirsten Dunst & Orlando Bloom

The two celebrities starred in Elizabethtown together, and also shined on the red carpet at the MTV VMAs, the year they reportedly dated...for a year.

Fiona Apple & David Blaine

These two were spreading some magic before the 1997 MTV VMAs. At this ceremony, Apple gave her famous "the world is bulls--t" acceptance speech.

Ashlee Simpson & Ryan Cabrera

She's married with kids today, but more than 15 ago, the songstress was going steady with her "On the Way Down" beau. Here they are at the 2004 MTV VMAs.

Ashlee Simpson & Pete Wentz

In 2008, the star popped up at the award show again on the arm of her then-husband. 

Hilary Duff & Joel Madden

Sure, this romance was so yesterday, but at the time, these two were living the lifestyles of the rich and famous together. Here they are at the 2005 MTV VMAs.

Pamela Anderson & Tommy Lee

This former Mr. and Mrs. made quite the splash on the MTV VMA red carpet in 1999. 

Cher & Richie Sambora

The pop icon and Bon Jovi's former guitarist stepped out together at the 1989 MTV VMAs when they were a new couple. They broke up the following year.

Pamela Anderson & Kid Rock

In 2001, the starlet was back at the show, that time with a new rock star. 

Paris Hilton & Benji Madden

While their relationship lasted less than a year, this duo managed to hit the 2008 MTV VMAs red carpet together before their split two months later. 

Sarah Jessica Parker & Robert Downey Jr.

Before she embarked on a 20-year-long marriage (and counting) to Matthew Broderick, the Sex and the City alum was going steady with the Avengers star between 1984 and 1991. They attended the 1990 MTV VMAs together.

Brad Pitt & Christina Applegate

As the story reportedly goes, these two went on one date and chose the 1989 MTV VMAs as the setting. However, she left mid-date for a mystery man and the two never went out again. 

Which couple did you totally forget about? Sound off in the comments!

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