Celebs Who Engaged In Love Triangles With Their Own Family

One of the cardinal rules of dating is never go out with a friends ex. This rule is broken all the time, and while those friendships are often left hurting a result, over time those wounds can heal. But when your sibling starts dating your ex, that's when things get really weird. Aside from the obvious gross factor, there's the potential ripple effect that could cause the entire family to choose sides, not to mention making the always awkward Thanksgiving dinner even worse. 

Does it get even weirder than that? Try dating your late sibling's widow, or your longtime partner's adopted daughter. Sounds like the kind of forbidden romances only a sleazy Hollywood screenwriter could cook up, right? We dig into those and more as we discuss  the stars who tossed taboo to the wind and got involved in love triangles within their own family. 

Hugh Hefner, the late Playboy founder took cradle-robbing to a whole new level when he dated twin sisters Karissa and Kristina Shannon at the same time. In October of 2008, Hefner found comfort in the 19-year-old twins in the wake of his breakup from the original The Girls Next Door stars, Holly Madison, Kendra Wilkinson, and Bridget Marquardt. The Shannon twins stepped into The Girls Next Door vacancy alongside Crystal Harris, who Hefner eventually married, so regardless of the innate nastiness of two sisters getting in on with the same old dude, they did somehow manage to help him transition to monogamy. Crystal and Hef remained married until his death in September 2017.

According to Karissa, the twins found Hefner's first rule of the mansion a tad difficult to follow. "We were not allowed to have boys in the house. ... That was one of the main reasons we moved out. But living there and being seen out with other guys, Hugh was tripping," she told The Sun (Via Contact Music). Hugh was nice enough to let them live in the guest house before eventually sending them packing for good in May of 2010, after which Karissa confirmed to The Celebrity Cafe what literally everyone had already speculated about this whole scandalous romance. "It's a whole new life. ... I got TV shows, a lot of experience, and stuff like that. I did a lot more covers for magazines. I did a commercial for Guitar Hero. There's just so much stuff and opportunities, it's just crazy," she said. Sounds like true love.

In May of 2015, Former Vice President Joe Biden's eldest son, Beau Biden (above right), died of brain cancer. By March of 2017, Beau's younger brother, Hunter Biden (above left), confirmed that although he was still technically married to his wife, Kathleen, he had begun a romantic relationship with Beau's widow, Hallie Biden. Yes, seriously. But hang on, because apparently the rest of the Biden clan is cool with this. "We are all lucky that Hunter and Hallie found each other as they were putting their lives together again after such sadness. They have mine and Jill's full and complete support and we are happy for them," the former Vice President said in a statement to Page Six. Not everyone is so thrilled, however, least of all, Kathleen Biden, Hunter's estranged wife.

In her divorce filing, Kathleen unloaded both barrels, accusing Hunter of infidelity, drug use, and squandering the family's money on "his own travel (at times multiple hotel rooms on the same night), gifts for other women, alcohol, strip clubs, or other personal indulgences," according to Page Six. Hunter also suffered previous embarrassments when his name popped up on the leaked list of Ashley Madison clients (though he denied ever using the site), and when he was dismissed from the Navy after testing positive for cocaine. So really, in the scope of all of that, is dating his dead brother's wife even that questionable? Page Six reports they broke up in 2019 anyway.

In one of the most convoluted webs of celebrity family love triangles ever, Kylie Jenner and her half brother Rob Kardashian have managed to turn their already reality-TV-famous brood into a spectacle of a whole other sort. They each dated one half of the formerly engaged couple Tyga & Blac Chyna, who also have a son together, and whose names sound like a mixed drink only college kids and drunk people on cruises order. 

Anyway, Tyga is an allegedly broke rapper who was on-again off-again with Kylie until around 2016 (but hey, there's always a chance he'll come back around following her split from Travis Scott). Blac Chyna is a former stripper turned fake eyelash mogul who had a baby with Rob Kardashian, and then promptly left him, according to TMZ. So, things are going great for this crew.

And since we've already mentioned that there are children in the mix here, let's go ahead and address the most obviously wacky part of the situation which is what happens in the weird Hollywood timeline where none of them ever broke up. If both sets of couples actually got married, Rob Kardashian would have become Uncle Step-Daddy to Blac and Tyga's son, King Cairo, and Kylie would have a stepson who is also the half brother of his cousin, Rob and Blac's daughter, Dream. That would certainly make that day in first grade where everyone presents a family tree to the class all kinds of uncomfortable.

Justin Bieber's association with the Kardashians started back in 2010 when he and Kim Kardashian did their now infamous The Graduate-themed photoshoot for Elle. She was 29, and he was 16 at the time, so the tabloids had a field day, although Kim quickly shot down any rumors of inappropriateness, according to MTV. Kim also allegedly tried to set the Canadian crooner up with one of her little sisters, which would prove to be something of a prophecy. 

Cut to 2015, when Kourtney Kardashian finally moved on from her long-time boyfriend and baby-daddy, Scott Disick, and she allegedly set out to make him jealous by hooking up with Bieber, according to US Magazine. Granted, we're dealing with 100% unsubstantiated rumors here, but just humor us. In turn, Lord Disick shacked up with Bieber's ex, Sofia Richie. Though both Bieber and Kardashian have both glossed over the rumors, they continued partying together which in Hollywood gossip terms means they were practically engaged. But hang on, because while the whole Justin/Kourtney drama was just picking up steam, he was also spotted arriving separately to the same club as Kendall Jenner — Sound the hookup alarm!

Does all this speculation from anonymous "sources" fan the flames of the guilty part of us would love to see a Justin Bieber vs. Scott Disick slap-fight? Maybe... But sadly, Biebs is now a married man who probably doesn't care.

Most of the dating drama involving Canadian rapper Drake centered on his romance with Rihanna. The "are they or aren't they?" between the "Work" duo has been raging since 2005, according to Vulture. But as far as we know, Drake hasn't also been pining for any of Rihanna's siblings for most of his life, and it seems like they're not even friends anymore, so that's not what this is about. This is about his ex-flame and Instagram model, Crystal Westbrooks, and the time she publicly shaded her sister, also Instagram model, India Love, for hooking up with Drake. It gets shady.

According to The Jasmine Brand, Crystal actually retracted her furious tweets, which accused her sis of "hopping on her exes...nvm nvm nvm." We can't be 100 percent sure what that means, but we're guessing it's not his bicycle.

Anyway, India never even confirmed their relationship, but because of Crystal's accusations and the fact that India was constantly backstage at his shows, people believed there was a least a groupie thing happening. Regardless of who did what with whom, no decent sister wants to be responsible for creating that reputation, so Crystal quickly stepped up and tweeted, "I reacted like an idiot to a story that I clearly knew nothing about nor was true. So sorry baby girl, love u more than u love french fries." Did both sisters get down with the rapper, then agree to cover it up? Only Drizzy knows.

As soon as Bella Thorne shed her Disney persona, she almost immediately transitioned into a social media celebrity by basically posting herself in a bikini everyday to either Snapchat, Instagram, or Twitter. It's a sure fire way to gain followers and has the added benefit of setting fire to any lingering relationship with children's television that you may have.

So, in continuation of her image makeover, Bella completed the trifecta by simultaneously ditching her long-term boyfriend, Gregg Sulkin, who also has Disney roots, acknowledged to her Twitter followers that she's bisexual, and then posted photos of herself making out with her brother's ex-girlfriend, Bella Pendergast while referring to her as "my soulmate" and "baby," according to Jezebel.

They were also spotted holding hands while going to a yoga class, but if they ever were a real couple, it was short-lived, because Thorne quickly swapped her brother's ex for her own ex, Gregg Sulkin's good pal, Tyler Posey, within a month, according to USA Today. Trying to keep up? Well, forget it, because Thorne ditched Posey a month later for Charlie Puth, who she's currently not with and who probably isn't somehow weirdly related to her, so this got really irrelevant really fast, didn't it?

When basketball legend Magic Johnson's son, EJ Johnson, got his big break with his E! reality show, EJNYC, he did not hesitate to drop a major bomb during the premiere episode. In a scandalous scene, EJ confronts his sister, Elisa Johnson, about her new boyfriend, a French model named Anthony.

According to EJ, Anthony allegedly "led him on" one night in a club so that EJ and his rich friends would treat him to VIP status. EJ even alleges that he and Anthony kissed, but that somehow didn't faze Elisa one bit who said, "My brother wants me to cut things off with Anthony, but I can't do that because I have developed serious feelings for him," according to The Daily Mail.

Two things about that: 1.) Does Anthony deny any part of this story? Because if he does, why would EJ have lied about that? And if he doesn't deny it, is Elisa just cool with her boyfriend making out with random dudes to get his bar tab paid? 2.) Is there a base requirement for something to be called a television show? Because watching rich family members arguing about hooking up with the same people has to be the lowest form of entertainment humanly possible. And that's comparing them with the Kardashians who have had entire segments of their show dedicated to Kim picking out flooring choices for her mansion.

Romantic entanglements have probably caused fighting in bands since humans were banging rocks together and dancing around a fire. The Beatles and Fleetwood Mac, arguably two of the greatest of all time, weren't even immune. So what chance did a bubblegum pop outfit like The Jonas Brothers have being infiltrated by a hottie like model Gigi Hadid, who Nick and Joe both dated. Fortunately, Gigi and Nick were never that serious — or the musical siblings were already ready to part ways — so it was no big deal when she and Joe started hooking up. So, while Gigi clearly had the potential to be the Yoko of the JoBros, that wasn't the case at all. Sorry, drama lovers.

Speaking with E! News, Nick couldn't have been more supportive of his big bro smoothing up on his former flame. He said, "I like them together. It's a good thing. Joe and I are best friends. We're each other's support system and closest friends, so naturally I'm gonna see a lot of her because they're together and it's great." Sounds legit, right? Best friends are always cool with it when one of them starts swapping spit with their ex. Just ask Denise Richards and Heather Locklear. 

Obviously, none of it matters now, because both Joe and Nick eventually married other women, actreses Sophie Turner and Priyanka Chopra, respectively, but it still begs the question: Did Gigi think Kevin was cute? 

It always seemed like out of the Kardashian/Jenner children, Caitlyn's lesser-known brood of Brody, Brandon, Burt, and Cassandra Jenner were the more down-to-earth group of siblings. Well, maybe that's just because they didn't get as much screen time, because on an episode of his podcast, The Brody Jenner & Dr. Mike Dow Podcast, Brody Jenner said he was his sister-in-law Leah's boyfriend before she married his brother, Brandon. Bonus gross: Brody was Brandon's best man at their wedding. Alright, we admit were intentionally blowing this out of proportion a bit.

Leah was also a guest on the infamous podcast where she quickly clarified (via US Weekly), "That is not true. 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."

Brody then admitted to the exaggeration, and joked the he shot her with a BB gun. Seriously, is it weirder to date the same girl as your brother, or to try to make people believe you did in a shameless effort to push an extra couple downloads of your podcast? We're pretty sure we know the answer to that. One last ironic twist to Brody's make-believe tale of shared sibling romance: His podcast description claims to be "a fresh take on relationship issues that young people face today." For what it's worth, both Brody and Brandon's marriages have ended since this whole thing — not that it's related — but maybe when it comes to his relationship advice: do what Brody says, not what he does.

This one is the mother of all strange family love triangles, because it crosses the line of siblings dividing over a lover and goes directly into the bizarro world of a father hooking up with his then-girlfriend's adoptive daughter, despite Soon-Yi's own protests to Time that Woody was in no way "a father or stepfather" to her. Okay. So that that makes it not at all odd that in her early twenties, she began a relationship with her mom's boyfriend who happened to be 35 years older than her, right? Oh, and hold that thought about him not being a father or stepfather to her, because Woody has something to say about that.

In a rare 2015 NPR interview, the Annie Hall director spoke candidly about his relationship with Soon-Yi, and he probably shouldn't have. Allen said, in part, "I was paternal. She responded to someone paternal. I liked her youth and energy. She deferred to me, and I was happy to give her an enormous amount of decision-making just as a gift and let her take charge of so many things. She flourished. It was just a good-luck thing." Welp, so much for that "not at all like my dad" stuff. But it actually somehow gets worse. "I started the relationship with her and I thought it would just be a fling, it wouldn't be serious. But it had a life of its own. And I never thought it would be anything more," he said. Yikes.