8 Celebs Who Had Awkward Encounters With Exes

Find out what happened during these awkward encounters …

Jessica Simpson had a close encounter with ex Tony Romo, over a decade after their split. The singer recently shared that Tony called her mother to tell her that he was going to sell the $100,000 speedboat that Jessica bought him in 2009. Jessica ended up having to sign paperwork for the sale — and in return, Tony gave her a very unimpressive thank you gift. 

“A couple weeks ago, my mom got a phone call. He’s calling my mom, saying, ‘Well, Tina, I’m selling the boat.’ And my mom’s like, ‘OK, and?’” Jessica shared. “He’s like ‘Well, Jessica’s name is still on the title.’ So, then I get paperwork, and I have to sign over this boat for him to sell.”

As a thank you, Jessica says he gave her “plastic cups,” adding, “I’m like, ‘Wow, I’m glad we didn’t work out.’”

Katy Perry once ended up getting seated right in front of her ex John Mayer when they were both attending a Sabrina Carpenter concert. In a video posted to social media, John could be seen sitting down behind Katy — and she reacted by dramatically grabbing the railing in front of her and then hiding her head in between her arms.

While Katy seemed totally embarrassed, she did turn around to say hi and shake John’s hand. It’s safe to say that the pair didn’t speak much for the rest of the evening.

In 2021, Jana Kramer had an awkward run-in with her ex Mike Caussin during a date night with her then-boyfriend, Jay Cutler. Looking back, Jana says it was “really hard” to see her ex flirting with other women — and to make matters worse, a photographer tried to get a photo of all three of them together. Jana shared that she also briefly spoke to Mike … but he didn’t think it was awkward at all. 

“You know what was hard? It looked so easy for him. Does that make sense? Where it’s, like, he didn’t look like it bothered him one second and that, like, hurt, you know? Because I was, like, he’s just untamed and uncaged and he’s happy,” Jana said on her Whine Down podcast.

She continued, “I was like, ‘This is awkward,’ and he’s like, ‘Not at all.’ And I was, like, ‘Ugh, OK.’ I’m glad that he was fine with [them both being out with other people] but at the same time…Just a little piece of me was kind of, like, it would’ve been nice [for him] to be like, ‘Yeah, this is hard, but I’m glad we can be cordial.’ That’s just, like, [an] acknowledgment that it might hurt a little bit. It was so strange.”

Mark Consuelos and his wife Kelly Ripa have ended up running into quite a few of his exes through the years. On one occasion, the couple were taking their son to an event near Kelly’s hometown in New Jersey and Mark started placing bets on how many of her ex-boyfriends they would see. It turns out that they actually ended up bumping into one of Mark’s exes instead!

At another point in time, Kelly says one of Mark’s exes was their server while they were at a fast food restaurant in Florida. 

“When you roll up to the drive-thru in Florida and the woman handing you your lunch says, ‘I used to date your husband,’ you don’t need to know anything else,” Kelly shared on their talk show.

Back in 2016, when Tyga was still dating Kylie Jenner, he had a tense encounter with ex Blac Chyna, who was dating Rob Kardashian at the time. Both couples were attending Khloé Kardashian’s birthday party when they bumped into each other — and it was all captured on their reality show, Rob & Chyna. While Kylie and Chyna tried to make polite conversation, Tyga looked completely uncomfortable and, after giving Chyna an awkward hug, he stepped away from the conversation.

In early 2025, Christina Haack ended up running into her estranged third husband Josh Hall while they were both dining at the same restaurant in California. Christina documented the awkward encounter on her Instagram story, sharing that she was dining with her daughter Taylor and her co-star Heather Rae El Moussa. While she didn’t share exactly what went down, she did seemingly refer to Josh using the snake emoji. 

“When you’re having a relaxing GNO with @heatherraeelmoussa and Tay and 🐍 shows up at your spot,” Christina wrote on her Instagram stories.

Hilaria Baldwin and her husband Alec Baldwin had an interesting run-in with one of her exes while he was performing on Broadway — and got naked on stage. While Hilaria didn’t share the actor’s name, she explained that while viewing a production of Take Me Out, the couple witnessed the man strip down for one of the scenes. 

“He was one of the loves of her life,” Alec shared on The Baldwins. “He was a very important boyfriend of hers. And we went to go see him on Broadway and he was naked — and as our British fans [would say], he had his bits out!”

He continued, “He’s there, her [ex-]boyfriend and I recognize him. I met before. And when he turns around with his [penis] hanging out, I’m like, oh, oh, oh, OK. He had like, a clarinet hanging from his pants. The guy literally turns around and we were all like, ‘Ah! Ah, whoa.’”

Country singer Chase Rice had an awkward encounter with an ex — and it was televised. Back in 2020, Chase was a musical guest on The Bachelor, but had no idea he was going to perform a private show for contestant Victoria Fuller, whom he had previously dated. While he knew Victoria was going to be on the show, he definitely didn’t expect to have such an intimate interaction. He added that he was actually pretty “pissed off” because he was there to promote his music, not to take part in the drama.

“So I told my manager and my publicist, they were like, ‘Don’t even worry about that,’” he said on the Fitz in the Morning radio show. “‘They’re not going to do that to you, that’s a weird coincidence, but they’re not gonna — there’s no way they would do that to you.’”

He continued, “They’ve never brought somebody else in like that, surprised the guest on the show. So the fact they did that to me, it’s over the top, it’s unnecessary, I didn’t expect it. But at the end of the day, it happened.”