Celebrity relationships can get messy. Sometimes, however, a celeb's ex's new relationship may hit a little too close to home.
Here are 14 times celebs allegedly dated, married, or hooked up with their family member or close friend's ex:
1. Tish Cyrus married Dominic Purcell, who — according to People — was reportedly in a prior "friends with benefits" relationship with her youngest daughter, Noah Cyrus.
According to the outlet, Tish allegedly began a relationship with Dominic after he and Noah stopped hooking up, and their relationship "offended" Noah.
When Tish and Dominic got married in 2023, Noah didn't attend the wedding.
2. Travis Barker and Paris Hilton had a brief on-and-off relationship in 2006. At the time, he had a crush on Paris's friend and then-closet organizer, Kim Kardashian. In 2007, Travis and Kim had a very brief relationship.
In his memoir Can I Say, Travis wrote, "We went to dinner, we went to lunch. You might think I would be doing the worst things with this girl because of her tapes, but it was the exact opposite of any other encounter I've had with a woman: With Kim, I wanted to be nothing but a gentleman to her. It was so weird... We’d be really sweet around each other, like little kids, and then when we were apart, she'd call me and say, ‘I want to see you again.’ ‘Me, too,’ I'd say."
He also maintains that they never slept together. He wrote, "Kim and I never touched each other. It just wasn’t meant to be."
3. Then, Travis Barker started dating Kim Kardashian's sister, Kourtney Kardashian, in 2021. They were longtime neighbors.
He told the LA Times, "It’s like, ‘Kourtney’s fans are worried about Travis. He’s a womanizer.’ Stop it. I obviously shared all that stuff [in my memoir] because I wanted to move past it. It was therapeutic for me... That’s her sister. She knows we used to talk. Nothing bad was going on. You give people a little information and they think they’ve solved the mystery of ‘this is why they’re fighting.’ It’s just so ridiculous."
Travis and Kourtney got married in 2022.
4. Best friends Kendall Jenner and Hailey Bieber were both reportedly romantically linked to Justin Bieber before he ultimately got back together with Hailey and married her in 2018.
From 2014–2015, dating rumors swirled around Kendall and Justin.
In 2014, she told Nightline, "He's a longtime friend of our family. Everybody loves to assume things, but no."
However, Justin seemingly suggested they'd casually dated, telling Billboard it was "never serious" between them.
Then, in 2016, he and Hailey dated for a short time, but their relationship ended in a "very dramatic excommunication." However, two years later, they reunited at a Miami church conference and got engaged a month later.
Hailey told Vogue, "The common denominator, I promise you, is always church. By then we were past the drama. I just gave him a hug. By the end of the conference, he was like, ‘We’re not going to be friends.’ I was like, ‘We’re not?’"
In a 2020 Instagram Live with the trio, Justin asked Kendall, "Quick question, did you see this coming?"
She replied, "See what coming? You two? ... Erm, honestly… No. I didn’t know but I think I hoped. Obviously Hales is my lady and my best friend and I, like, wanted it so bad for both of you."
5. Justin Bieber was also reportedly "hooking up on and off for a few months" with Kendall Jenner's older sister, Kourtney Kardashian, in 2016, according to People via an anonymous source.
In late 2015, Justin responded to early rumors about their relationship, jokingly telling The Bert Show, "I'm being used, man. What can I say? ... Nah, we'll leave it at that."
By the beginning of 2017, Kourtney was reportedly "finished hooking up with Justin" and "serious" about working out her relationship with her long-term on-and-off-again partner, Scott Disick.
6. Demi Moore reportedly dated both Pink Taco founder Harry Morton and his father, Hard Rock Café co-founder Peter Morton.
She was reportedly with Harry for six months before they split in May 2013. Then, she was romantically linked to Peter in September 2013.
7. After finally ending her on-and-off relationship with Huddy (aka Chase Hudson), Charli D'Amelio started dating his friend (and the son of his musical mentor, Travis Barker) Landon Barker. This reportedly inspired Chase to write "All the Things I Hate About You," which includes the line, "You’re a showstopper / a bad liar / homie hopper / drama starter."
Charli and Chase originally dated from early 2019 to mid-2020, when they broke up amid rumors that he'd cheated on her. However, after several months and a bit of public back and forth, they got back together. They continued to be on-and-off-again until early 2022.
Then, she and Landon went public with their relationship that summer.
Chase released "All the Things I Hate About You" in July 2022. A month later, Landon reportedly clarified his relationship timeline with Charli in a TikTok comment, writing, "I feel you, but to clear up the confusion, I didn’t steal her from him. They broke up six months ago. Me and Huddy were friends, never best friends."
However, they broke up in early 2024. On his Instagram story, Landon said, "Hey everyone, I would like to let you guys know that Charli and I are no longer together. We broke up to focus on ourselves. We are still friends and have so much love for each other. I am incredibly grateful for the time we shared and hope you can respect our decisions. Thank you, love you all so much!"
8. Jake Paul and Alissa Violet were romantically linked from 2015–2017. They were "just hooking up," but she wanted a real relationship. At one point, when she was upset with Jake for not letting her go on a snowboarding trip with him, she hooked up with his brother, Logan Paul.
In the YouTube docuseries The Mind of Jake Paul, Alissa said, "Jake lied and said that I cheated, but we were never together. One weekend he was going snowboarding with his friends and I wanted to go, and he was like, 'Oh no, you need to stay here.' I was so pissed off, I was so fed up, I was so hurt, I was so disgusted, I was at my breaking point. I hit up Logan and was like, ‘Let’s hang out.’ Then me and Logan hooked up and I’m still disgusted by it. It’s not who I am and it’s not who I ever wanted to be."
Jake said, "A lot of reason why I didn’t talk about the situation is to defend my brother and that’s why. Alissa and I always really liked each other. We were always like dating, not really. It was a rocky relationship. I wasn’t, at the time, mature enough to know how to be a boyfriend. We would get into arguments and be fighting and go through ups and downs. Basically, I did a bunch of things that pissed her off, and she wanted to get revenge, I guess is the word. It was just me not knowing how to treat her. It was just a bad situation, we just drove each other mad. I remember when I confronted her about [Logan], her justification was that ‘You made me do this.’ And I think it’s because then we were on and off for a year and a half, I would go off and be with other girls, and she would go and be with other guys. [Logan] basically said, ‘Oh I didn’t think you guys were actually a thing and that you were actually dating.'"
9. Longtime besties Selena Gomez and Taylor Swift first met in 2008 on a double date with their then-boyfriends, Nick and Joe Jonas. The following year, both women had short-lived relationships with Taylor Lautner.
10. In 2015, Gigi Hadid had a five-month relationship with her close friend Taylor Swift's ex, Joe Jonas.
Taylor and Joe's brief relationship infamously ended in a 27-second phone call in 2008.
However, Taylor and her then-boyfriend, Calvin Harris, hung out with Gigi and Joe.
At the time, Taylor told Vanity Fair, "We even have girls in our group who have dated the same people. It's almost like the sisterhood has such a higher place on the list of priorities for us. It's so much more important than some guy that it didn't work out with...just because you have the same taste in men, we don't hold that against each other."
11. Heather Locklear and Denise Richards were close friends until Denise began dating Richie Sambora shortly after he and Heather filed for divorce.
Heather and Richie got married in 1994, then filed for divorce in 2006. During their marriage, they became friends with Denise and her then-husband, Charlie Sheen, because Heather and Charlie costarred on Spin City for several years.
However, Denise and Charlie were also going through a high-profile divorce in 2006, which is something she and Richie bonded over.
She told People, "My mother has cancer and Richie’s father has cancer. It’s hard. Thank God Richie and I have each other not only to go through divorce, but to go through both our parents being ill."
She also denied that she'd broken up her friends' marriage, telling Entertainment Tonight, "We didn’t meddle in marriages and anything like that."
She also said, "The thing with Heather, that’s been hard. You know you can’t help who you fall for and that friendship, unfortunately, was done and wasn’t salvageable. ... You know, she wasn’t my best friend. She was a close friend in the last couple of years. I hadn’t known her my whole life... [It’s] been tough having people think that I’m such a crappy friend."
Denise and Richie reportedly broke up in 2012.
12. In the late '90s, Adam Duritz of Counting Crows reportedly had nearly back-to-back relationships with close friends/Friends costars Jennifer Aniston and Courteney Cox.
Adam and Jennifer briefly dated in 1995, then he had a short relationship with Courteney, who starred in his band's "A Long December" music video in 1997.
In 2014, he told Men's Health, "I don't like that it became the only thing they wrote [in the tabloids], but that's their problem. It wasn't great for me, it wasn't great for my band. But it's nothing I did. I'm not gonna link people's idiocy to my choices, because those were perfectly reasonable choices. They were nice girls and I went out with them and that was that."
13. In 2019, Barrie Drewitt-Barlow, who became famous in 1999 when he and his then-partner Tony became the UK's first gay couple to welcome a child via surrogacy, reportedly divorced Tony so he could be with their daughter's ex-boyfriend, Scott Hutchinson.
Saffron, who's Barrie and Tony's daughter, had reportedly ended her relationship with Scott several months before his "unexpected" relationship with Barrie began.
For a time, all three men reportedly lived in Barrie and Tony's mansion.
Barrie and Scott later got married and started a family together.
14. And finally, Debbie Reynolds befriended Elizabeth Taylor early in her career, and when they were married (to Eddie Fisher and Mike Todd, respectively), they were often spotted on double dates. However, a year into Elizabeth and Mike's marriage, he unexpectedly died in a plane crash. Soon after, she began an affair with Eddie, who ultimately divorced Debbie and married Elizabeth on the same day.
Elizabeth and Eddie were married from 1959–1964.
In 1966, when both of the women were remarried, they unexpectedly crossed paths on a cruise ship.
Debbie told HuffPost, "We got on the same boat to go to Europe — the Queen Elizabeth. I sent a note to her and she sent a note to me in passing, and then we had dinner together. She was married to Richard Burton by then. I had been remarried at that point. And we just said, 'Let's call it a day.' And we got smashed. And we had a great evening, and stayed friends since then."
They even costarred in These Old Broads in 2001.