8 Well-known Households With Awkward Courting Histories

Discover out which movie star family members share each genes and exes…

Damon Wayans lately admitted that again within the early 2000s, one in every of his severe girlfriends really used thus far his nephew. Whereas he didn’t identify any names, he says that he first met the lady in 2001 and fell in love at first sight — however had no concept she had beforehand been in a relationship together with his nephew. When he later uncovered her relationship historical past, Damon says he chalked it as much as the slim California relationship pool however made positive it was cool together with his nephew.

“I’m like, you realize ‘What’s up?’ and he’s like, ‘That’s you.’ And I’m like, ‘Okay, cross the Courvoisier, let’s go!’ And I went forward and I fell in love, and it was okay!” Damon stated on the Membership Shay Shay podcast.

In the meantime, Damon’s brother Marlon says it’s not the one time he’s stolen a member of the family’s girlfriend. He advised TMZ that Damon was a “girlfriend-stealing bandit.”

Tish Cyrus married her husband Dominic Purcell again in August 2023 — however her daughter Noah opted to not attend the marriage. Rumors later surfaced that Noah had really been casually relationship Dominic, 20 years her senior, simply earlier than he related with Tish. The mother-daughter duo reportedly by no means mentioned the scenario earlier than the marriage.

“Noah and Dominic have been seeing one another in a associates with advantages manner, on and off. They stopped seeing one another after which Tish began one thing up. Tish knew he had been seeing Noah,” a supply advised Individuals. “Tish by no means gave Noah the possibility to speak about all of this earlier than they bought married.”

Nobody concerned has ever addressed the rumors though Tish and Noah have seemingly reconciled, showing in a TikTok collectively in April 2025.

By the years, Justin Bieber has been a detailed buddy of the Kardashian-Jenner household and he’s allegedly connected with greater than one of many sisters. Each Kendall Jenner and her older sister Kourtney Kardashian are rumored to have dated Justin, though they haven’t formally confirmed it.

As for Justin, he advised Billboard in 2015 that his relationship with Kendall was “by no means severe,” however didn’t fairly shut down the rumors about his romance with Kourtney when he was requested about it on a radio present the next 12 months. Proper round that point, Kourtney was even noticed by TMZ spending a late night time at Justin’s resort. It’s even been urged that Justin is the daddy of Kourtney’s son Reign — however the 10-year-old lately denied the rumors.

Demi Moore is rumored to have dated movie star restaurateur Peter Morton and his son Harry Morton. Again in early 2013, Demi was noticed getting dinner with Harry, who was 19 years her junior. Whereas TMZ reported the pair have been spending time collectively, it hadn’t but developed right into a relationship. Then, just some months later, E! Information reported that the pair had the truth is been relationship however gone their separate methods.

Later that 12 months, Demi was linked to Harry’s father Peter, who based Onerous Rock Café. Whereas relationship rumors swirled, the couple by no means made issues official. Demi seems to have remained near the household by means of the years although and was noticed at Harry’s funeral in 2019, in accordance with TMZ.

Brandon Jenner’s ex-wife Leah was a buddy of the household for years earlier than the pair tied the knot — which means she has an extended historical past with Brandon and his brother Brody. In truth, Leah and Brody had a flirtatious relationship after they have been preteens, lengthy earlier than Leah started relationship Brandon. Wanting again, Leah defined how understanding Brody led her to Brandon.

“We’ve identified one another since we have been 11 years previous; I used to be 11 years previous, Brandon was 13,” Leah shared on The Brody Jenner Podcast with Dr. Mike Dow. “We began taking part in [music] in highschool collectively. I had a boyfriend; he had a girlfriend. After which after I was single at some point, he was single at some point and he got here as much as me and he’s like, ‘I’ve been in love with you because you have been 11 years previous.’”

Brody then joked that he was the highschool boyfriend and that issues bought “actually awkward.” Whereas Leah denied Brody’s declare, she did confess to a preteen romance saying, “I met Brandon by means of Brody. We went to highschool collectively after we have been 11. Okay, 11. You don’t kiss, you don’t make out, you don’t maintain fingers, you beat one another up, you play basketball…So he was my boyfriend within the fifth grade, Brody was [but] we by no means kissed.”

Kourtney Kardashian and Travis Barker could also be fortunately married however years earlier than their romance started, Travis was linked to Kourtney’s sister Kim. In truth, in Travis’ memoir, Can I Say: Residing Giant, Dishonest Demise, and Drums, Drums, Drums, he confessed to having a crush on Kim and attempting to pursue her. He wrote that again in 2006 he met Kim whereas she was working as Paris Hilton’s closet organizer and thought she was “sizzling.” They ended up on a visit to Amsterdamn collectively and after they returned to LA, they continued to see one another — however Travis careworn it was harmless and never a bodily relationship.

“We went to dinner, we went to lunch,” Travis wrote within the e book. “You would possibly assume I’d be doing the worst issues with this woman due to her tapes, nevertheless it was the precise reverse of another encounter I’ve had with a lady: with Kim, I needed to be nothing however a gentleman to her. It was so bizarre.”

Whereas issues didn’t work out between them, Travis went on to attach with Kourtney years later. Though rumors have swirled that Travis’ reference to Kim is why Kourtney is commonly feuding along with her sister, Travis says that’s not the case.

“[Kourtney] is aware of we used to speak. Nothing unhealthy was occurring. You give folks a bit of data they usually assume they’ve solved the thriller of ‘this is the reason they’re combating.’ It’s simply so ridiculous,” Travis advised the Los Angeles Occasions in 2023.

Jake Paul and Logan Paul have lengthy been identified for his or her wild on-line antics and drama — and a few of that was attributable to Jake’s then-girlfriend Alissa Violet. Whereas Alissa was linked to Jake between 2015 and 2017, their romance was on-and-off and issues have been by no means actually official. Annoyed and damage that Jake wouldn’t take their relationship severely, Alissa admits she ended up hooking up together with his brother Logan out of anger.

“One weekend [Jake] was going snowboarding together with his associates and I needed to go, and he was like, ‘Oh no, you must keep right here.’ I used to be so pissed off, I used to be so fed up, I used to be so damage, I used to be so disgusted, I used to be at my breaking level,” Alissa defined on YouTube docuseries The Thoughts of Jake Paul. “I hit up Logan and was like, ‘Let’s hang around.’ Then me and Logan connected and I’m nonetheless disgusted by it. It’s not who I’m and it’s not who I ever needed to be.”

Jake later opened up concerning the scenario, admitting that whereas he “actually preferred” Alissa, he was not “mature sufficient” to be an actual boyfriend to her they usually ended up in a “unhealthy scenario” that drove one another mad.

“I keep in mind after I confronted her about [Logan], her justification was that ‘you made me do that,’” Jake recalled. “And I believe it’s as a result of then we have been on and off for a 12 months and a half, I’d go off and be with different women, and she or he would go and be with different guys. [Logan] mainly stated, ‘Oh I didn’t assume you guys have been really a factor and that you just have been really relationship.’”

Brothers Jermaine Jackson and Randy Jackson each have youngsters with the identical girl. Again within the late Nineteen Eighties, Randy was linked to designer Alejandra Oaziaza. Collectively they welcomed two youngsters however they by no means tied the knot. They finally cut up within the early Nineteen Nineties.

Not lengthy after, Alejandra started relationship Randy’s older brother Jermaine and by March 1995, the pair have been married. They went on to welcome three youngsters of their very own however the relationship reportedly precipitated a lot strife within the household. Jermaine and Randy’s mom Katherine allegedly didn’t approve and Jermaine was furious that his brother would marry his ex-girlfriend. Amid the household drama, Jermaine and Alejandra separated in 2004.