See Every Single MTV Video Music Awards Couple We Wish Were Still Together

From Pete Davidson and Ariana Grande to Justin Timberlake and Britney Spears, prepare to be blown away by all the couples who walked the MTV VMAs in happier times.

By Mike Vulpo Aug 30, 2020 7:00 PMTags
Watch: What the MTV VMAs Looked Like 10 Years Ago

There's nothing quite like date night at the MTV Video Music Awards.

Over the years, Hollywood's hottest couples have made MTV's annual award show the opportunity to showcase their love for one another. In fact, some have made their red carpet debut as a twosome at the star-studded event. Yes, we're talking about you Ariana Grande and Pete Davidson.

But as celebrities prepare to participate in a virtual show this year because of the Coronavirus pandemic, it may just be the perfect time to remind pop culture fans of all the famous stars who once attended the show with a special plus one.

Back in 2004, Newlyweds was one of reality TV's biggest shows with Nick Lachey and Jessica Simpson turning heads for all the right reasons on the red carpet.

There was also the night Justin Bieber and Selena Gomez were the perfect match at the 2011 MTV VMAs. Anyone else feeling nostalgic right now?

photos
MTV VMAs: Riskiest Fashion Moments of All-Time

In honor of tonight's telecast, we decided to travel back in time and look back on all the couples who definitely once attended the MTV VMAs as a united pair.

While they've all moved on, there may be more than a few couples who we can't help but wish were still together. Keep scrolling below and you'll understand. 

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 carpet...it 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. 

Mark your calendars! The 2020 MTV VMAs air Sunday night at 8 p.m. only on MTV. 

Watch Daily Pop weekdays at 11 a.m., only on E!.