Celebrities dating each other’s friends isn’t something new, but dating a family member’s ex is a bit more uncommon — and definitely more taboo.
Damon Wayans Sr. confirmed in April 2025 that in the early 2000s he dated his nephew’s ex-girlfriend after falling “in love.”
Kourtney Kardashian, meanwhile, had a fling with Justin Bieber in 2015 after he was rumored to have dated her younger sister Kendall Jenner. Kourtney’s husband, Travis Barker, also had a “crush” on her sister Kim Kardashian before they tied the knot in 2022.
Hunter Biden, for his part, had a full-fledged romance with his sister-in-law Hallie Biden after her husband (and his brother) Beau Biden died. While the relationship was unconventional, the pair did get their family’s blessing.
“We are all lucky that Hunter and Hallie found each other as they were putting their lives together again after such sadness,” former President Joe Biden said in a March 2017 statement. “They have mine and Jill’s full and complete support and we are happy for them.”
Scroll down to see which celeb families have dated each other’s exes:
Damon Wayans Sr. and Nephew
Wayans Sr. revealed in April 2025 that he was once “in love” with his nephew’s ex-girlfriend in 2001 or 2002. During an appearance on the “Club Shay Shay” podcast, he explained that he knew the woman was his nephew’s ex when he pursued her. “So I got divorced and I was by myself for two years, and then I saw her and I was like, ‘Oh, my God, I’m in love,’” Wayans Sr. recalled.
Wayans Sr. explained that he had asked his nephew at the time to see if it was OK for him to date the woman. “[The nephew was] like, ‘That’s you,’ and I’m like, ‘OK, pass the Courvoisier, let’s go,’” Wayans Sr. said.
Tish Cyrus and Noah Cyrus
Us Weekly broke the news in March 2024 that Noah Cyrus had been “seeing” Dominic Purcell when her mom, Tish Cyrus, also started “pursuing” the actor. Noah, the youngest daughter of Tish and ex-husband Billy Ray Cyrus, allegedly was involved with Purcell for about eight or nine months.
Tish started dating Purcell in 2022 and the pair got married in August 2023. Neither Tish nor Noah publicly addressed the relationship overlap, but the mother-daughter duo’s falling out was visible when Noah didn’t attend her mother’s wedding. A source exclusively told Us at the time that Noah wasn’t invited to the ceremony.
Kourtney Kardashian and Kim Kardashian
Barker bonded with Kim when he was dating Paris Hilton, and although he fessed up to having a “crush” on her at the time, he claimed nothing physical happened. “How could you not stare at Kim? Mind you, I enjoyed hanging out with Paris, but I love curvy girls,” Barker wrote in his 2015 memoir, Can I Say: Living Large, Cheating Death, and Drums, Drums, Drums, recalling a trip they all took to Amsterdam years prior. “Kim was eye candy. I was in no way disrespectful to Paris, but I couldn’t keep my eyes off Kim.”
After Barker broke up with Hilton, he said he remained close with Kim. “We were around each other a lot,” he recalled. “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.” The Blink 182 drummer, however, alleged, “Kim and I never touched each other. It just wasn’t meant to be.”
In October 2023, Barker told the Los Angeles Times that his now-wife, Kourtney, “knows” he and her sister Kim “used to talk.” He once again claimed, “Nothing bad was going on.”
Barker and Kourtney began dating in 2020 and they got married in May 2022. They welcomed their first baby, son Rocky, in November 2023. (Kourtney also shares three children with ex Scott Disick, while Barker shares two children and a stepdaughter with ex-wife Shanna Moakler.)
Logan Paul and Jake Paul
Alissa Violet revealed in 2018 that she hooked up with Logan Paul while she was seeing his brother Jake Paul. Violet was romantically linked to Jake from 2015 to 2017 but claimed in the YouTube docuseries The Mind of Jake Paul that they were “never together.”
She alleged in the series, which premiered in September 2018, that she didn’t cheat on Jake, but she did sleep with Logan out of anger. “One weekend [Jake] 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,” Violet recalled. “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 confessed in the same docuseries that he “really liked” Violet but he was not “mature enough” to be a real boyfriend to 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,’” Jake remembered. “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.’”
Kourtney Kardashian and Kendall Jenner
Bieber was rumored to have briefly dated Jenner in fall 2014. Billboard reported in November 2015 that Bieber said he was “never serious” with Jenner, hinting that the rumors were correct. Bieber was linked to Jenner’s oldest sister, Kourtney, in late 2015 after Kourtney split from Disick.
“Justin started hanging out with Kourtney alone because she started going out more,” a source exclusively told Us in December 2015. “He’s been showing her a good time.” In January 2016, Bieber played coy about the fling, calling Kourtney “great” during an appearance on The Bert Show, but denied anything romantic was going on. Justin married Jenner’s BFF Hailey Bieber in 2018.
Karissa Shannon and Kristina Shannon
Hugh Hefner began dating twins Karissa and Kristina Shannon in October 2008 after they moved into the Playboy Mansion. He was also dating Crystal Harris at the same time, whom he married in 2012. Hefner’s relationship with the Shannon sisters fizzled out by May 2010 when they moved out of his home. (Hefner and Harris remained married until his death in September 2017 at age 91.)
Hunter Biden and Beau Biden
Hunter confirmed in March 2017 that he was in a relationship with his late brother Beau’s widow, Hallie. The relationship came nine months after Beau died following a battle with brain cancer at the age of 46.
Hunter and Hallie split in 2019 after two years of dating. “We were together and trying to do the right thing. And that grief turned into a hope for a love that maybe could replace what we lost,” Hunter told CBS’s Tracy Smith in April 2021. “Well, I made a lot of decisions that I probably shouldn’t have made. There was a lot more compassion and understanding from the people that knew me. But it was a horrible time, too.”
Hunter was previously married to Kathleen Biden for 22 years before their divorce in October 2015. The exes share three children. Hunter married Melissa Biden in May 2019, and they welcomed their only son, Beau, in March 2020.
Hallie, meanwhile, was married to Beau for 13 years and welcomed daughter Natalie and son Robert II before his death.
Brandon Jenner and Brody Jenner
Brandon Jenner was married to Leah Jenner from 2012 to 2019, and they share daughter Eva, born in July 2015. In June 2014, Brandon’s younger brother Brody Jenner revealed he had a relationship with Leah when they were kids.
“We’ve known each other since we were 11 years old; I was 11 years old, he was 13,” Leah revealed during an appearance on “The Brody Jenner Podcast with Dr. Mike Dow,” explaining when she met Brandon. “We started playing [music] in high school together. I had a boyfriend; he had a girlfriend. And then when I was single one day, he was single one day and he came up to me and he’s like, ‘I’ve been in love with you since you were 11 years old.’”
Brody interrupted his then-sister-in-law, revealing, “The boyfriend at the time was me. That’s what made it really awkward.” Leah claimed, “That is not true,” explaining, “I met Brandon through Brody. We went to school together when we were 11. OK, 11. You don’t kiss, you don’t make out, you don’t hold hands, you beat each other up, you play basketball.”
Leah eventually confessed Brody was “my boyfriend in the fifth grade,” but was adamant, “We never kissed.”
Jermaine Jackson and Randy Jackson
Randy Jackson dated designer Alejandra Oaziaza for several years after meeting in 1986 when he was 24 and she was 17, according to The New York Post. The pair welcomed daughter Genevieve in 1989 and son Steven in 1992 before calling it quits.
Oaziaza moved on with Randy’s older brother Jermaine Jackson, whom she wed in March 1995. Oaziaza shares two children with the former Jackson 5 singer: Jaafar and Jermajesty born in July 1996 and October 2000, respectively. Oaziaza and Jermaine were married eight years before Jermaine filed for divorce in 2008.
In addition to her four children from Randy and Jermaine, Oaziaza also raised Katherine and Joe Jackson’s adopted son, Donte Jackson. Jermaine, for his part, is also the father of Jermaine La Jaune “Jay” Jr. born in January 1977, Autumn born in June 1978 and Jaimy born in March 1987 from his first marriage to Hazel Gordy. Jermaine shares sons Jeremy and Jourdynn, born in December 1986 and January 1989, with ex Margaret Maldonado.
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