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 PM
| Updated Jul 31, 2020 1:50 PM
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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. 

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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.

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 debut as a couple at the 2018 MTV VMAs.

Pete Davidson & Cazzie David

The SNL alum and Larry David's daughter dated for two years before splitting in 2018. But first they attended the 2017 MTV VMAs together.

Noah Cyrus & Lil Xan

Miley Cyrus' little sister and the rapper made their red carpet debut 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 Jonas Brothers band mates, Nick Jonas and Kevin Jonas.

Jessica Simpson & Nick Lachey

The then-spouses seemed like they wanted to leave each other forever when they attended the 2004 MTV VMA red carpet. They also attended the 2005 show together before calling it quits a year later.

Kristen Stewart & Michael Angarano

A year before she dated her Twilight co-star Robert Pattinson, the actress (now wed to screenwriter Dylan Meyer) was in a relationship with her Speak co-star. They attended the 2008 MTV VMAs together.

Wiz Khalifa & Amber Rose

The model and the rapper attended the 2014 MTV VMAs together, one 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

Before the musician was burnin' up for now-wife Priyanka Chopra and she was teammed up with NFL running back Christian McCaffrey, they attended the 2014 ceremony as a couple. 

Iggy Azalea & Nick Young

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

Eva Longoria & Nelly

It was getting a bit "Hot In Herre" when Longoria posed with the musician at the 2005 event. 

Kanye West & Amber Rose

We're gonna let you finish scrolling through, just wanted to let you know that a year before West and his then-girlfriend ended their two-year romance, they turned up at the 2009 show so he could borrow the mic from Taylor Swift. 

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 in 2005.

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

"On the Way Down" to Simpson and Cabrera finding their forever partners, they attended 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 is so yesterday, but at the time of the 2005 VMAs, these two were living the lifestyles of the rich and famous together. 

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 actress was back at the iconic show 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 wed Matthew Broderick, the Sex and the City alum was going steady with the Avengers star. Before they ended their seven-year romance in 1991, they attended the 1990 MTV VMAs together.

Brad Pitt & Christina Applegate

As the story 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!