8 Well-known Households With Awkward Courting Histories

Discover out which superstar kin share each genes and exes…

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

“I’m like, you already know ‘What’s up?’ and he’s like, ‘That’s you.’ And I’m like, ‘Okay, move 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 informed 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 courting Dominic, 20 years her senior, simply earlier than he linked with Tish. The mother-daughter duo reportedly by no means mentioned the scenario earlier than the marriage.

“Noah and Dominic had been seeing one another in a associates with advantages means, on and off. They stopped seeing one another after which Tish began one thing up. Tish knew he had been seeing Noah,” a supply informed Folks. “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 attached 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 informed Billboard in 2015 that his relationship with Kendall was “by no means critical,” 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 yr. Proper round that point, Kourtney was even noticed by TMZ spending a late night time at Justin’s resort. It’s even been advised that Justin is the daddy of Kourtney’s son Reign — however the 10-year-old just lately denied the rumors.

Demi Moore is rumored to have dated superstar 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 had 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 in actual fact been courting however gone their separate methods.

Later that yr, Demi was linked to Harry’s father Peter, who based Laborious Rock Café. Whereas courting 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, based on 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. Actually, Leah and Brody had a flirtatious relationship after they had been preteens, lengthy earlier than Leah started courting Brandon. Wanting again, Leah defined how understanding Brody led her to Brandon.

“We’ve recognized one another since we had 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 once 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 had 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 high school collectively once we had 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. Actually, in Travis’ memoir, Can I Say: Dwelling Massive, Dishonest Dying, and Drums, Drums, Drums, he confessed to having a crush on Kim and making an attempt 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 “scorching.” 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 may suppose I might be doing the worst issues with this woman due to her tapes, but it surely was the precise reverse of every other 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 happening. You give individuals a bit data and so they suppose they’ve solved the thriller of ‘because of this they’re combating.’ It’s simply so ridiculous,” Travis informed the Los Angeles Occasions in 2023.

Jake Paul and Logan Paul have lengthy been recognized 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 had been by no means really official. Annoyed and damage that Jake wouldn’t take their relationship critically, 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, it is advisable 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 attached 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 appreciated” Alissa, he was not “mature sufficient” to be an actual boyfriend to her and so they ended up in a “unhealthy scenario” that drove one another mad.

“I bear in mind once I confronted her about [Logan], her justification was that ‘you made me do that,’” Jake recalled. “And I feel it’s as a result of then we had been on and off for a yr and a half, I might go off and be with different women, and she or he would go and be with different guys. [Logan] principally stated, ‘Oh I didn’t suppose you guys had been really a factor and that you simply had been really courting.’”

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

Not lengthy after, Alejandra started courting Randy’s older brother Jermaine and by March 1995, the pair had been married. They went on to welcome three kids 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.