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Unconventional Celebrity Romances: When Stars Date Family Members’ Exes
In the world of celebrity relationships, dating amongst friends is not unheard of; however, embarking on a romance with a family member’s former partner is decidedly less conventional and often considered a taboo affair. This article delves into instances where famous figures have navigated these complex relationship dynamics, exploring the intricacies of love, loyalty, and family.
Notable Instances of Celebrities Dating Family Exes
Damon Wayans Sr. made a candid revelation in April 2025, acknowledging that in the early 2000s, he was romantically involved with his nephew’s former girlfriend, stating he had genuinely “fallen in love”.
Kourtney Kardashian‘s past romantic history includes a speculated fling with Justin Bieber in 2015, following rumors of his connection with her younger sister, Kendall Jenner. Adding another layer to this intertwined web, Kourtney’s current husband, Travis Barker, had previously confessed to having a “crush” on her sister Kim Kardashian before they married in 2022.
Hunter Biden‘s relationship with his sister-in-law, Hallie Biden, after the passing of his brother Beau Biden, represents another instance of navigating unconventional romantic terrain. Despite the unusual circumstances, their union reportedly received familial support.
Former President Joe Biden publicly commented on Hunter and Hallie’s bond in a March 2017 statement: “We are all fortunate that Hunter and Hallie discovered solace in each other as they reconstructed their lives following immense grief. They have our complete endorsement, and we are delighted for them.”
Continue scrolling to discover more celebrity families who have experienced dating within their extended circles:
Damon Wayans Sr. and His Nephew’s Ex
In an April 2025 podcast appearance, Damon Wayans Sr. disclosed his past “love” for his nephew’s former girlfriend around 2001 or 2002. During his conversation on “Club Shay Shay,” he recounted that he was aware of her prior relationship with his nephew when he pursued her romantically. “I divorced and was single for two years, then I encountered her and it was like, ‘Wow, I’m smitten,'” Wayans Sr. reminisced.
Wayans Sr. further clarified that he sought his nephew’s consent before dating the woman. He quoted his nephew’s permissive response as, “‘That’s your decision,’ and I thought, ‘Excellent, let’s proceed.'”
Tish Cyrus and Noah Cyrus
Reports surfaced in March 2024 via Us Weekly indicating that Noah Cyrus was romantically involved with Dominic Purcell when her mother, Tish Cyrus, also began a romantic pursuit of the actor. Noah, the youngest daughter of Tish and her former husband Billy Ray Cyrus, was reportedly linked to Purcell for approximately eight to nine months prior to her mother’s involvement.
Tish initiated her relationship with Purcell in 2022, culminating in their marriage in August 2023. Neither Tish nor Noah publicly addressed the overlapping relationships, but the rift between the mother and daughter became apparent when Noah was absent from her mother’s wedding. Sources speaking to Us at the time claimed Noah was not invited to the nuptials.
Kourtney Kardashian and Kim Kardashian with Travis Barker
Before his relationship with Kourtney, Barker developed a rapport with Kim during his time dating Paris Hilton. He admitted to having a “crush” on Kim, though maintained their interactions remained platonic. Recounting a trip to Amsterdam in his 2015 memoir, Can I Say: Living Large, Cheating Death, and Drums, Drums, Drums, Barker wrote, “Kim was undeniably attractive. While I enjoyed Paris’ company, I am drawn to women with curves. I was never disrespectful to Paris, but Kim was captivating.”
Following his separation from Hilton, Barker stated his bond with Kim persisted. “We socialized frequently,” he recalled. “Our interactions were affectionate, almost childlike, and when apart, she would contact me expressing her desire to see me again, and I reciprocated.” However, Barker asserted, “Our relationship never progressed physically. It simply wasn’t destined to be.”
In a 2023 interview with the Los Angeles Times, Barker mentioned that Kourtney, his wife, is aware of his past conversations with Kim. He reiterated his stance: “Nothing inappropriate transpired.”
Barker and Kourtney’s relationship commenced in 2020, leading to their wedding in May 2022. They welcomed their son, Rocky, in November 2023. (Kourtney also has three children with former partner Scott Disick, and Barker has two children and a stepdaughter with ex-wife Shanna Moakler.)
Logan Paul and Jake Paul with Alissa Violet
Alissa Violet revealed in 2018 that she had a romantic encounter with Logan Paul while she was in a relationship with his brother, Jake Paul. Violet was linked to Jake from 2015 to 2017, but stated in the YouTube docuseries The Mind of Jake Paul that their relationship was never officially defined.
In the docuseries, which premiered in September 2018, she claimed she did not cheat on Jake but engaged with Logan out of resentment. “One weekend [Jake] planned a snowboarding trip with friends and excluded me. I was infuriated, frustrated, hurt, and disgusted—at my breaking point,” Violet recounted. “I contacted Logan and suggested we spend time together. Subsequently, Logan and I were intimate, a decision I still regret. It is out of character for me and not who I aspire to be.”
Jake admitted in the same docuseries that he “genuinely liked” Violet but lacked the “maturity” to be a committed boyfriend. “It was a toxic dynamic; we consistently provoked each other. I recall when I confronted her about [Logan], her defense was that ‘you instigated this,'” Jake remembered. “Our relationship was tumultuous for a year and a half; I would pursue other women, and she would reciprocate with other men. [Logan]’s perspective was, ‘I didn’t realize your relationship was serious.'”
Kourtney Kardashian and Kendall Jenner with Justin Bieber
Speculation arose regarding a brief romance between Bieber and Jenner in fall 2014. Billboard reported in November 2015 that Bieber dismissed any seriousness in his connection with Jenner, seemingly confirming the rumors. Later, Bieber was linked to Jenner’s eldest sister, Kourtney, in late 2015, after Kourtney’s separation from Disick.
“Justin began spending time with Kourtney alone as she started socializing more,” an insider told Us in December 2015. “He’s been showing her enjoyable experiences.” In a January 2016 appearance on The Bert Show, Bieber remained ambiguous about the fling, describing Kourtney as “wonderful” but denying any romantic involvement. Justin eventually married Jenner’s close friend, Hailey Bieber, in 2018.
Karissa Shannon and Kristina Shannon with Hugh Hefner
Hugh Hefner started dating twins Karissa and Kristina Shannon in October 2008, after they moved into the Playboy Mansion. He was also in a concurrent relationship with Crystal Harris, whom he married in 2012. Hefner’s relationship with the Shannon sisters concluded by May 2010 when they departed from his residence. (Hefner and Harris remained married until his death in September 2017 at age 91.)
Hunter Biden and Beau Biden with Hallie Biden
Hunter verified in March 2017 his relationship with Hallie, the widow of his late brother Beau. This relationship began nine months after Beau’s death due to brain cancer at the age of 46.
Hunter and Hallie ended their relationship in 2019 after two years. “We were together, seeking to navigate a challenging situation. Our shared grief evolved into a hope for a love that could potentially fill the void of our loss,” Hunter explained to CBS’s Tracy Smith in April 2021. “However, I made questionable choices. I received considerable compassion and understanding from those close to me, but it was nonetheless an incredibly difficult period.”
Prior to this, Hunter was married to Kathleen Biden for 22 years until their divorce in October 2015. They share three children. Hunter married Melissa Biden in May 2019, and they welcomed their son, Beau, in March 2020.
Hallie was married to Beau for 13 years, and they have two children, Natalie and Robert II, before his passing.
Brandon Jenner and Brody Jenner with Leah Jenner
Brandon Jenner was married to Leah Jenner from 2012 to 2019, and they have a daughter, Eva, born in July 2015. In June 2014, Brandon’s younger brother, Brody Jenner, disclosed he had a past relationship with Leah during their childhood.
“We’ve known each other since we were young; I was 11, he was 13,” Leah revealed on “The Brody Jenner Podcast with Dr. Mike Dow,” detailing when she first met Brandon. “We started playing music together in high school. I had a boyfriend; he had a girlfriend. Then, when we were both single, he approached me and said, ‘I’ve been in love with you since you were 11.'”
Brody interrupted, revealing, “I was the boyfriend at that time, making it quite awkward.” Leah countered, “That’s incorrect,” clarifying, “I met Brandon through Brody. We attended school together at 11. At 11, there’s no kissing, no making out, no holding hands, just playful fighting and basketball.”
Leah eventually conceded that Brody was “my boyfriend in fifth grade” but insisted, “We never kissed.”
Jermaine Jackson and Randy Jackson with Alejandra Oaziaza
Randy Jackson and designer Alejandra Oaziaza were in a relationship for several years after meeting in 1986, according to The New York Post. They had a daughter, Genevieve, in 1989 and a son, Steven, in 1992 before separating.
Oaziaza then became involved with Randy’s older brother, Jermaine Jackson, marrying him in March 1995. With Jermaine, Oaziaza has two children: Jaafar and Jermajesty, born in July 1996 and October 2000, respectively. Oaziaza and Jermaine were married for eight years before Jermaine filed for divorce in 2008.
In addition to her four children with Randy and Jermaine, Oaziaza also raised Katherine and Joe Jackson’s adopted son, Donte Jackson. Jermaine also has other children from previous relationships: Jermaine La Jaune “Jay” Jr., Autumn, Jaimy, Jeremy, and Jourdynn.