Uncomfortable Much? 15 Awkward Celebrity Ex Encounters

August 27, 2013  |  
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Anybody who’s ever run into an ex unexpectedly knows how awkward the whole thing can be. Whether it’s at a wedding, a club, a family event or just at the supermarket, seeing a former flame always seems to involve increased heart rates, sunken stomach feelings and fake pleasantries. And with celebs it’s surely no different. Although they typically hire schedulers and publicists to ensure that they never have to face or even discuss an ex, some situations are just unavoidable – like these 15 awkward, celebrity ex encounters.

When Drake Accepted The BET Award For “What’s My Name”

Possibly the most awkward BET Awards moment ever – and you know there have been plenty – was when the winner for the Coca-Cola Viewer’s Choice Award was first announced as Chris Brown – then as Rihanna – and then as Drake, who appeared onstage to accept the award. Clearly there was no best way to handle this situation, but Drizzy’s simple comment of “Well, that was awkward” probably summed it up most accurately.

When Ciara Stopped By 106 & Park

In July of this year, Ciara stopped by 106 & Park to promote her album and new single “Body Party.” But soon after Ci walked onstage, it was clear that the focus was less about her music and more about her interactions with her interviewers – who just happened to be ex-boyfriend Bow Wow and his ex-girlfriend Angela Simmons. We’ll admit, the three did a pretty good job of keeping it about business, but smiles and jokes couldn’t hide all of the visible awkwardness – namely, Angela trying too hard to be attentive and Bow trying too hard to be cool.

Eve Constantly Answering Questions About Stevie J.

Eve has made it very clear time and time again that she wasn’t exactly in the best headspace when she dated Stevie J. Yet she continues to be asked uncomfortable questions about him, and forced to give equally uncomfortable answers. In 2012, Eve said it best and simplest during her interview with Hot 97’s Angie Martinez: “What can I say, I was young and dumb.” Weren’t we all?

When Drake Performed At The 2013 MTV VMA’s

It’s always fun to watch celebrities’ interactions at awards shows. And at this particular show, when Drake stepped onstage to perform a mashup of “Hold on We’re Going Home” and “Started From the Bottom,” all eyes were on Rihanna. The two have been rumored to be “back on” lately after splitting up in 2011, but based on RiRi’s face, we’re not sure if they’re dating again or if she just felt awkward.

When Cameron Diaz Saw Ex Justin Timberlake Flirting With Jessica Biel

Back in 2007 after breaking up with longtime boyfriend Justin Timberlake, Cameron Diaz reportedly spotted the singer flirting it up with Jessica Biel at a Golden Globes After Party. But instead of keeping it classy, Cameron was said to have “blown up” at Jessica and stalked Justin to another party, where the two carried on an awkward conversation about the whole thing.

When KFed And Shar Both Appeared On Celebrity Fit Club

In 2010, exes Kevin Federline and Shar Jackson both appeared on the same season of Celebrity Fit Club, making for a pretty awkward show. The two did successfully lose weight, but didn’t seem to make much progress in terms of mending their tumultuous relationship until the final episode, when Kevin apologized to a tearful Shar for being a selfish a-hole.

When A Paparazzo Asked Kim About Reggie Bush – In Front Of Kanye

It’s clear that Kanye’s conflict resolution skills aren’t exactly on point. But back in 2012 when a slick paparazzo asked Kim whether she would be congratulating Reggie Bush on his girlfriend’s pregnancy, Kanyeezy lost it. Infuriated by the pap’s boldness and probably very uncomfortable to begin with, (we know Kim and her exes is a sensitive subject for him), he attempted to slap the woman’s camera away before hopping in his ride, angrily.

When James Cameron and Kathryn Bigelow Were Nominated For the Same Award

At the 2010 Academy Awards, directors and ex-spouses James Cameron and Kathryn Bigelow competed for Best Picture. But it was Kathryn’s film, The Hurt Locker, that won out over James Cameron’s Avatar. When all was said and done, the two attempted to ease the awkwardness by playfully pretending (we hope) to choke each other.

When Stevie J Showed Up At Nikko’s Video Screening Party

We know it’s staged ratchetness and whatnot, but how painfully awkward was it to watch Stevie J pop his messy behind up at Mimi and Nikko’s video release party? And when he presented Mimi with a brand new car and clowned Nikko in one fell swoop – Mimi knew she should’ve never invited Stevie there in the first place.

When Taylor Swift Accepted A Ripple Of Hope Award

In 2012, Taylor Swift was honored with a Ripple of Hope Award and presented it by none other than Robert F. Kennedy himself. Problem is, Robert Kennedy just happens to be the father of Conor Kennedy, Taylor’s ex-boyfriend of only one month at the time.

Rihanna and Chris Brown In General

Ever since that horrific domestic violence incident and their breaking up, Rihanna and Chris Brown have had a difficult time navigating interviews, award shows and regular nights out at the club whenever the focus has been the two of them as a couple. Remember Rihanna’s interview with Oprah when she described how she felt running into Chris and Karrueche at a party? Awkward. And we definitely know the feeling.

When Jessica Simpson And Her Boo Ran Into Nick Lachey And His Boo

While dining at a Los Angeles restaurant, Jessica Simpson and baby daddy Eric Johnson reportedly ran into Nick Lachey and now-wife Vanessa Minnillo. According to reports, the couples didn’t interact or make a big deal out of it, and instead chose to just ignore each other. Always a smart move in an uncomfortable situation.

When Taylor Swift Was Seated Near Taylor Lautner

When you’ve dated as many people as Taylor Swift has, it’s inevitable that you’d run into an ex or two from time to time. At an awards show – mere weeks after breaking up with Taylor Lautner –coordinators seated Taylor just six measly seats away from him. Taylor has said of the incident that the two were “fighting this silent war of ‘I don’t care that you’re here’.”

In other words, awk-ward!

Bow Wow And Angela Simmons Hosting 106 & Park

I haven’t watched 106 & Park regularly since Free and AJ left, but of the few episodes I have seen it’s hard to deny that Bow Wow and Angela are still a bit uncomfortable balancing being exes and co-hosts. Plus, it probably doesn’t help that the two have faced rumors of “still being in love” for years now.

When Camille Grammar Met Kelsey’s New Wife

In 2011, Camille Grammar ran into ex-husband Kelsey Grammar and met his new wife Kayte. Of the awkward incident, Camille said “It was a little uncomfortable at first, but then I met her and I shook her hand. And I looked into her eyes, and I thought, ‘She’s OK, she’s nice.’”

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