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15 Times Celeb Exes Awkwardly Ran Into Each Other

Entertainment
15 Times Celeb Exes Awkwardly Ran Into Each Other

There is nothing more awkward than running into an ex. You got rid of that person for a reason, and it doesn’t help when they constantly show up in your life, especially if you are both celebrities. Running into one another at red carpet events, clubs, or even a sports game is just plain awkward, but unfortunately, it is a very common occurrence for Hollywood stars.

It also doesn’t help when you run into multiple celeb exes. Take for example, Jennifer Lopez, who has dated a number of A-list stars and seems to always be at the same place they are. While J-Lo was dating dancer Casper Smart, they both awkwardly ran into her ex, rapper Diddy, at the Weinstein Golden Globes after party. Jenny From the Block got into another very unusual situation when she attended the Latin Music Awards and her ex, Marc Anthony, was there with his new wife, who looks so much like Lopez it’s a little scary.

You can’t really do much when you run into an ex, celebrity or not. However things may have ended between you two, you either briefly hug and move on or do your best to ignore the other person as much as you can. Hide if you have too!

Check out this list of the 15 Times Celeb Exes Awkwardly Ran Into Each Other, and you might find out that you’ve had a somewhat similar experience with one of your exes.

15. Jennifer Lopez And Diddy – Rapper Exchanges Awkward Handshake With Casper Smart

Photo Via: nydailynews.com

When Jennifer Lopez was dating a much younger Casper Smart, the two awkwardly ran into J-Lo’s ex, rapper Diddy. It happened during the Weinstein Golden Globes after party and thankfully, there were no punches being thrown. In fact, it looked like the singer introduced her young man to Diddy, and both men shared a friendly handshake. Jennifer and Diddy dated back in 1999, but ended their relationship in 2001 because she suspected that Didddy was cheating. Sean “Diddy” Combs still thinks of J-Lo as his great love and even told Extra that he approved of her new love life with baseball star Alex Rodriguez.

14. Jay Z And Rachel Roy – Awkward Run-In With Rachel Roy Ends Up Becoming Infamous Elevator Feud With Solange Knowles

via Life & Style

We were all a little confused when Beyonce‘s sister, Solange, attacked Jay Z on the elevator that infamous night after the 2014 Met Ball. Security footage showed Solange hitting the rapper, and we were all puzzled about what on earth caused her to lash out at Queen Bee’s man. However, it appeared that the whole elevator fiasco was because of Jay Z’s infidelities. According to a number of reports, Jay Z was hooking up with Rachel Roy for a period of time behind Beyonce’s back. It was also said that the feud started after he was seen talking to Roy at the after party. Jay Z’s awkward run-in with Roy seemed to be a huge issue with Solange, who was defending her older sis. Hopefully, the rapper learns his boundaries or we might just get another tell-all album by Beyonce.

13. Nick Cannon And Selita Ebanks – Exes Ended Up Appearing On The Same Talk Show

via YouTube

Nick Cannon and Victoria’s Secret model Selita Ebanks were engaged in 2007, but that didn’t last long. The model even blasted Cannon, saying, “I mean, I technically wore a ring, but I don’t think I was really engaged. I want a prince.” What made the matters even worse was when the two appeared on Katie Couric‘s talk show and winded up sitting next to each other. Cannon tried to make things a little less awkward after telling Couric they were once engaged. He also put his arm around the model, and it just looked extremely uncomfortable. After Cannon asked Ebanks, “What? You didn’t want to sit next to me?” Banks didn’t answer and the whole situation was just way too difficult to watch.

12. Terry McMillan And Jonathan Plummer – Husband Comes Out As Gay, Both Appear On The Oprah Show To Discuss Relationship Failure

via Oprah.com

Terry McMillan was 43 years old when she met a then-20-year-old Jonathan Plummer in Jamaica. She was old enough to be his mother, but Plummer didn’t care and the two married in 1998 and Terry moved him into her multimillion-dollar home. Six years into the marriage, Plummer blindsided Terry when he came out as gay. After a divorce in 2005 and a huge feud all over the media, the former couple awkwardly appeared on The Oprah Show to discuss their relationship. Going on the show didn’t help the former couple at all, and Terry slapped Jonathan with a $40 million lawsuit for emotional distress. However, she withdrew the case before it went to trial. They both appeared on the show again, and Terry told Oprah that she had forgiven him.

11. Swizz Beats And Mashonda – Spotted Vacationing Together With Current Wife, Alicia Keys

Photo Via: centrictv.com

R&B artist Mashonda and Swizz Beats began dating in 2008 and married in 2004. They welcomed a son in 2006 named Kasseem David Dean, Jr. but soon parted ways in April of 2008. Back in 2014, Swizz Beats was photographed on vacation with his two sons, his current wife, Alicia Keys, and Mashonda. It was awkward at the time because Mashonda accused him of carrying a romantic affair with Keys while they were still together. So it was awkward AF to see the three out vacationing together. According to Beats, Mashonda just so happened to be at the same place Keys and Beats were flying too. However, they did spend a lot of time together regardless of Mashonda blasting the couple all over social media.

10. Chris Brown And Rihanna – Spotted Leaving The Same Club With Another Girl On Brown’s Arm

Photo Via: lifestyle.one

We are all very familiar with the Chris Brown and Rihanna domestic violence incident that left the singer bruised and beaten. RiRi left Chris for good, following the altercation, and Brown started dating Karrueche Tran right after. On January 10, both Rihanna and Chris Brown were photographed leaving the same club in New York. It would have been very awkward for the former couple to have crossed path’s that night, especially with all that happened between them. That same night, Brown was spotted holding hands with a woman named Vanessa Vargas. Now, that would have been super odd if they met in the club!

9. Bradley Cooper And Zoe Saldana – Gritted Their Teeth After Breaking Up And Having To Take Photos Together For A Film

via El Espectador

Former lovers Bradley Cooper and Zoe Saldana had to grit their teeth when they reunited for a film they both starred in together. Before breaking up, the Hollywood couple both starred in The Words. However, they called it quits at the wrong time and had to take photos together at the film’s premiere. The two looked extremely uncomfortable together as they posed for photos on the film’s red carpet. They only dated for a short three months, and the photos are excruciating to look at.

8. Demi Moore And Bruce Willis – Take Way Too Many Awkward Photos With Family

Photo Via: nydailynews.com

Remember when Demi Moore and Ashton Kutcher got married in 2005? The couple had a sixteen-year age gap at the time and what made it even more strange was that Kutcher and Demi’s daughter, Rumer Willis, were a lot closer in age than he was with his ex-wife! But what makes these exes run-ins awkward are the times Demi’s ex-husband, Bruce Willis, would show up with the family for photo ops. There are multiple photos of Demi, Ashton, her three kids, and Bruce standing side by side like everything is normal. It’s actually painful to look at.

7. Mollie King And David Gandy – Love Of Tennis In Common Brings Them Awkwardly Back Together

Photo Via: cosmopolitan.com

Mollie King and David Gandy had a 10-month romance before calling it quits in February of 2012. However, their love of tennis brought the former couple back together, and it didn’t look pleasant one bit. Mollie and David ended up sitting right next to one another during a tennis match between Rafael Nadal and Novak Djokovic. Photos show Mollie trying her best to keep her composure, and the tension between the two could literally be cut with a knife. In fact, it was so awkward for the two that a friend quickly swapped places with David. It definitely looked like they were trying to ignore both of their presence. Maybe next time they should carefully check their seats before purchasing them.

6. Simon Cowell And Sinitta – Pop Mogul Awkwardly Discussed Having An Abortion In The ’80s While Cowell Welcomed Son

via Yahoo News UK

Simon Cowell and Sinitta had a long romance and dated on and off for 20 years. In 2013, Sinitta opened up about the time she made the decision to terminate her pregnancy in the 1980’s. Apparently, it left both of the stars devastated. However, she believed they were both too young to have a child. However, Sinitta has been all over the media explaining how she regrets having an abortion. It’s definitely not something the X Factor wants to hear, especially since he’s dating another woman named Lauren Silverman and just welcomed a son named Eric in 2013. It’s a bit awkward that Sinitta brought up the abortion the same year Cowell welcomed his baby. She’s even admitted that she still loves Cowell! Hopefully, these two don’t cross the same paths in the future.

5. Taylor Swift And John Mayer – Bumped Into Each Other At Gigi Hadid’s Birthday Bash

Photo Via: TMZ.com

Taylor Swift has dated a few Hollywood stars, so it’s not surprising that she and one of her exes would be at the same place. While she was celebrating model Gigi Hadid‘s birthday at The Nice Guy in Los Angeles, her BFF made the mistake of inviting singer John Mayer. Isn’t the number one girl code to not invite your best friend’s ex? Guess Gigi forgot that rule. It isn’t clear if the two exes spoke during the birthday bash, but the restaurant is supposedly small, and they had to at least give one or two glances to each other. Luckily, Gigi invited a lot of A-list stars, and we’re positive that Swift had her girl army on top of her the entire night. But how funny would it be if Taylor actually made another song about an ex and bumping into him at a birthday bash? That would be one catchy tune.

4. Ellie Goulding And Ed Sheeran – Share Rather Awkward Embrace At VS Fashion Show

via Autodo

Ed Sheeran made headlines when he released his song “Don’t” and how it was inspired by ex Ellie Goulding, who reportedly cheated on him with One Direction member Niall Horan. However, Goulding slammed those rumors and reports of cheating in an issue of Elle UK, but she didn’t hide the fact that she did go on a few dates with Horan. Despite their ugly breakup, they seemed to hash things out when they were both attending the 2014 Victoria’s Secret Fashion Show. Photos captured the two embracing with a hug, but it was anything but normal. They looked extremely uncomfortable sharing a hug and even Goulding’s assistant seemed confused about what was going on. Sheeran looked like he was forcing a smile and just wanted to get the hug over with. It was a very, very awkward moment for both stars.

3. Harry Styles, Kendall Jenner, And Cara Delevingne – Former One Direction Member Has “Friendly” Chat With Both Exes

J-14.com

Harry Styles was in a very awkward situation when he and his two exes, Kendall Jenner and Cara Delevingne, all bumped into one another during the British Fashion Awards. Harry was about to make his way down the stairs when the ladies, holding hands, walked up stairs and bumped into each other. It was rumored that the former One Direction star was linked to both stars—at different times, of course. It also appeared that the friendship between the two ladies only grew stronger since dating the same man. A photo of the three stars that London night seems like it was extremely awkward for Harry. Maybe he should stick to dating non-celebs.

2. Jennifer Lopez And Marc Anthony – Anthony’s Wife Splits From Latin Singer Less Than 24 Hours After He Shares Kiss With J-Lo

via Mirror

Marc Anthony and Jennifer Lopez have a ton of history together and even have two kids, but they couldn’t make their relationship work. Both stars had moved on since their split in 2014, and Anthony even remarried to a woman named Shannon De Lima who looked a lot like Jenny from the block. However, it looked like Lopez and Anthony couldn’t let their love die and shocked the world when they shared a kiss at the Latin Grammy Awards in 2016. It was so awkward that Anthony’s wife reportedly split with him less than 24 hours after the very public smooch!

1. Orlando Bloom And Miranda Kerr – Share Awkward Kiss At Oscars After Party

via abc7.com

Orlando Bloom thought it was a good idea to interrupt his ex Victoria’s Secret model Miranda Kerr‘s interview at an Oscars after party and share a rather embarrassing kiss. After spotting his gorgeous ex-wife on the red carpet at the Vanity Fair party, he decided to stop her interview and ask her how she was doing. He also couldn’t help but tell Kerr that she looked amazing in her dress. It appeared to be very awkward for the people surrounding the former couple and to Kerr who was surprised at the interruption. Your loss, Bloom!

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