We Ranked Celebrity Ex Run Ins From Least Awkward to OMG

Which former couple had the most uncomfortable encounter?

By Meg Swertlow Apr 25, 2017 12:27 AMTags

The last thing you do when you break up with someone is run into that person—anywhere, ever. But when you're a celeb and you run in the same star-studded circles as your ex, it's bound to happen, and it's bound to be awkward! 

Over the weekend, Katy Perry and Orlando Bloom proved just that.

The former flames, who split earlier this year, had a semi-awkward run-in when they both attended the 40th birthday bash of jewelry designer Jennifer Meyer at the Peppermint Club in West Hollywood, Calif. Fellow guest Erin Foster posted an Instagram video showing the two chatting. While the two could have had a frosty or a feisty interaction, it seems like the one-time lovers let bygones be bygones. 

That got us thinking...

There have been hundreds of these kind of bust ups over the years, but which celebs have had the most potentially awkward ex encounters? We've got five of them, and we've ranked the run-ins from least to most soul crushing. Check it out...

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Hotter After Breakup: Celeb Breakovers!
Stefanie Keenan/Getty Images; Mike Marsland/WireImage

Taylor Swift & Harry Styles: Back in 2014, T-Swift, ran into her former British beau at the Weinstein post-Oscar party at the Montage Beverly Hills in 2014. Two years earlier, Tay famously wrote her hit tune "I Knew You Were Trouble" about her rocky relationship with the One Direction crooner, but it was all water under the bridge. 

We rate this one: Only Awkward if You Make It Awkward

Roger / AKM-GSI, AKM-GSI

Kendall Jenner & Chandler Parsons: Next up, we've got Kenny running into the NBA player at the Beverly Hills Bentley dealership, earlier this year on Jan. 2. The two had a short, alleged fling back in 2014, so it didn't seem like there was a lot of substance to their steamy hook up, but they both looked uncomfortable to see each other. E! News reported at the time that there wasn't a lot of drama with the accidental meet up, but the two definitely had an icy interaction—no hugs hello or goodbye. 

We rate this one: Awkward City, Population: Kendall and Chandler

E!

Lana & Isaiah Mustafa: Total Divas star Lana bumped into her Old Spice actor ex in Las Vegas and things went well, a little too well possibly. The two seemed to get along famously, and things only got awkward after the run in when the pro wrestler went running to her fiancé Rusev filled with fears (and tears) over their impending marriage. It's never a good thing when you see your ex man and it makes you cry to your current man!

We rate this one: This Is Mostly Awkward for Us

Vasquez-Max Lopes/AKM-GSI

Katy Perry & Orlando Bloom: Days after their break up, Katy looked like she could cut glass with the glance she flashed Orly at the Vanity Fair in February, but the arctic look wasn't exactly what it seemed. After a bunch of hubbub was made the two exes were feuding, the "Roar" singer tweeted, "U can still b friends & love ur former partners! No one's a victim or a villain, get a life y'all!"

So while their Oscars encounter may have appeared to be full-throttle awkward, their most recent run-in proves the two former loves have an easy, breezy relationship.

We rate this one: Not Awkward at All

E!

Tyga & Blac Chyna: Nothing tops the awkwardness that has been Chyna dating Rob, whose sister is on-again, off-again with Chyna's ex. 

Needless to say there's been more than one uncomfortable run-in with the close-knit family, but the one takes the (birthday) cake is when Chyna came face to face with Kylie and Tyga at Khloe Kardashian's birthday party back in 2016. Of course all the other fam was there, knocking the awkward factor out of the park.

We rate this one: Super Awkward