8 Famous Families With Awkward Dating Histories

Find out which celebrity relatives share both genes and exes…

Damon Wayans recently admitted that back in the early 2000s, one of his serious girlfriends actually used to date his nephew. While he didn’t name any names, he says that he first met the woman in 2001 and fell in love at first sight -- but had no idea she had previously been in a relationship with his nephew. When he later uncovered her dating history, Damon says he chalked it up to the slim California dating pool but made sure it was cool with his nephew.

“I’m like, you know ‘What’s up?’ and he’s like, ‘That’s you.’ And I’m like, ‘Okay, pass the Courvoisier, let’s go!’ And I went ahead and I fell in love, and it was okay!" Damon said on the Club Shay Shay podcast.

Meanwhile, Damon’s brother Marlon says it’s not the only time he’s stolen a family member’s girlfriend. He told TMZ that Damon was a “girlfriend-stealing bandit.”

Tish Cyrus married her husband Dominic Purcell back in August 2023 -- but her daughter Noah opted not to attend the wedding. Rumors later surfaced that Noah had actually been casually dating Dominic, 20 years her senior, just before he connected with Tish. The mother-daughter duo never discussed the situation before the wedding, a source told People.

“Noah and Dominic were seeing each other in a friends with benefits way, off and on. They stopped seeing each other and then Tish started something up. Tish knew he had been seeing Noah,” the source said. “Tish never gave Noah the chance to talk about all of this before they got married.”

No one involved has ever addressed the rumors, although Tish and Noah have seemingly reconciled, appearing in a TikTok together in April 2025.

Through the years, Justin Bieber has been a close friend of the Kardashian-Jenner family and he’s allegedly hooked up with more than one of the sisters. Both Kendall Jenner and her older sister Kourtney Kardashian are rumored to have dated Justin, although they haven’t formally confirmed it.

As for Justin, he told Billboard in 2015 that his relationship with Kendall was “never serious,” but didn’t quite shut down the rumors about his romance with Kourtney when he was asked about it on a radio show the following year. Right around that time, Kourtney was even spotted by TMZ spending a late night at Justin’s hotel. It’s even been suggested that Justin is the father of Kourtney’s son Reign -- but the 10-year-old recently denied the rumors.

Demi Moore is rumored to have dated celebrity restaurateur Peter Morton and his son Harry Morton. Back in early 2013, Demi was spotted getting dinner with Harry, who was 19 years her junior. While TMZ reported the pair were spending time together, it hadn’t yet developed into a relationship. Then, just a few months later, E! News reported that the pair had in fact been dating but gone their separate ways.

Later that year, Demi was linked to Harry’s father, Peter, who founded Hard Rock Café. While dating rumors swirled, the couple never made things official. Demi appears to have remained close to the family through the years though, and was spotted at Harry’s funeral in 2019, according to TMZ.

Brandon Jenner’s ex-wife, Leah, was a friend of the family for years before the pair tied the knot -- meaning she has a long history with Brandon and his brother Brody. In fact, Leah and Brody had a flirtatious relationship when they were preteens, long before Leah began dating Brandon. Looking back, Leah explained how knowing Brody led her to Brandon.

“We’ve known each other since we were 11 years old; I was 11 years old, Brandon was 13,” Leah shared on The Brody Jenner Podcast with Dr. Mike Dow. “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 then joked that he was the high school boyfriend and that things got “really awkward.” While Leah denied Brody’s claim, she did confess to a preteen romance saying, “I met Brandon through Brody. We went to school together when we were 11. Okay, 11. You don’t kiss, you don’t make out, you don’t hold hands, you beat each other up, you play basketball…So he was my boyfriend in the fifth grade, Brody was [but] we never kissed."

Kourtney Kardashian and Travis Barker may be happily married but years before their romance began, Travis was linked to Kourtney’s sister Kim. In fact, in Travis’ memoir, Can I Say: Living Large, Cheating Death, and Drums, Drums, Drums, he confessed to having a crush on Kim and trying to pursue her. He wrote that back in 2006, he met Kim while she was working as Paris Hilton’s closet organizer and thought she was “hot.” They ended up on a trip to Amsterdam together, and when they returned to LA, they continued to see each other -- but Travis stressed it was innocent and not a physical relationship.

“We went to dinner, we went to lunch,” Travis wrote in the book. “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.”

While things didn’t work out between them, Travis went on to connect with Kourtney years later. Although fans speculated in the past that Travis’ connection with Kim was why Kourtney was often feuding with her sister, Travis says that’s not the case.

“[Kourtney] 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 told the Los Angeles Times in 2023.

Jake Paul and Logan Paul have long been known for their wild online antics and drama -- and some of that was caused by Jake’s then-girlfriend Alissa Violet. While Alissa was linked to Jake between 2015 and 2017, their romance was on-and-off and things were never truly official. Frustrated and hurt that Jake wouldn’t take their relationship seriously, Alissa admits she ended up hooking up with his brother 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,” Alissa explained on YouTube docuseries The Mind of Jake Paul. “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 later opened up about the situation, admitting that while he “really liked” Alissa, he was not “mature enough” to be a real boyfriend to her and they ended up in a “bad situation” that drove each other mad.

“I remember when I confronted her about [Logan], her justification was that ‘you made me do this,’” Jake recalled. “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.’”

Brothers Jermaine Jackson and Randy Jackson both have children with the same woman. Back in the late 1980s, Randy was linked to designer Alejandra Oaziaza. Together they welcomed two children but they never tied the knot. They eventually split in the early 1990s.

Not long after, Alejandra began dating Randy’s older brother Jermaine and by March 1995, the pair were married. They went on to welcome three children of their own but the relationship reportedly caused much strife in the family. Jermaine and Randy’s mother Katherine allegedly did not approve and Jermaine was livid that his brother would marry his ex-girlfriend. Amid the family drama, Jermaine and Alejandra separated in 2004.