What’s the first thing you think of when you think about love triangles?
Well, the first thing is probably “don’t get in one,” and that’s a good call. The second question, though, is likely to be “who would actually want all the drama of being in a love triangle?”
That kind of drama might drive most people off, but not celebrities. In fact, some drama-loving celebs have gotten into the messiest kind of love triangle: one involving their own family members!
Don’t believe it? Keep reading to learn about these crazy love triangles and the celebs at their center.
Hugh Hefner and the Shannon twins
Hugh Hefner was rich, famous, and one of the world’s most infamous horndogs. Therefore, we should have expected his rebounds to be as outsize as his reputation. We saw this in action when Hefner broke up with the three Girls Next Door stars Holly Madison, Kendra Wilkinson, and Bridget Marquardt and hooked up with two 19-year-old twins: Karissa and Kristina Shannon.
The optics of an old, lecherous dude hooking up with teenage twins were pretty bad. However, it seems like everyone got what they wanted out of this relationship. As The Celebrity Cafe reports, Karissa later described what the fame (infamy?) of hooking up with Hefner led to. “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.”
At the time, it seemed the ladies had few regrets about the relationship. Since Hefner’s death, though, they have been very vocal about how unpleasant being Hefner’s girlfriends really was.
Drake, Crystal Westbrooks, and India Love
When Drake causes drama involving women, you might think he is just texting an underage girl again. However, one of his wilder bits of drama came from his relationship with the Westbrooks sisters.
At one point, Drake was hot and heavy with Crystal Westbrooks, an Instagram model. So far, so good…until Crystal accused her sister and fellow Instagram model India Love of hooking up with Drake as well. The Jasmine Brand reports that Westbrooks wrote a series of angry tweets about the matter that she later deleted, including one complaining about her sister “hopping on her exes…nvm nvm nvm.”
Westbrooks eventually apologized for her reaction, and India Love never even confirmed hooking up with Drake. But given that Love was constantly making backstage appearances at Drake shows, Westbrooks’ claims seem more than a bit plausible.
Gigi Hadid, Nick Jonas, and Joe Jonas
Some celebrity love triangles are a bit more positive than others. Surprisingly, they don’t get more positive and supportive than what went down between the Jonas Brothers and Gigi Hadid.
First, Nick Jonas and Hadid were dating, though things may not have been very serious at all. Before you know it, though, she started hooking up with Joe Jonas. At this point, drama lovers around the world were watching very closely, wondering if Hadid might be the Yoko Ono to break up this particular musical group.
Fortunately for Jonas Brothers fans, this was not the case. In an interview with E! News, Nick Jonas revealed how excited he was for his brother and Hadid’s relationship. “I like them together. It’s a good thing,” he said. “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.”
Neither man ended up marrying Hadid, of course. But it’s nice to see their brief love triangle didn’t cause any long-term drama or tension within the family.
Justin Bieber, Kourtney Kardashian, and Kendall Jenner
Ok, fair warning: this next love triangle is mostly made of rumor and gossip. But it has more than a few pinches of truth to it, and it was simply too spicy for us not to share!
Back in 2015, Kourtney Kardashian broke up with Scott Disick. According to InTouch Weekly, she may have wanted to make Disick jealous and decided the most expedient way to do so was to hook up with Justin Bieber. In response, Disick hooked up with Bieber’s own ex, Sofia Richie.
Disick’s stunt aside, Bieber and Kardashian seemed to enjoy hanging and partying together, leading many to think they were a real item. However, Cheat Sheet reports that Bieber soon had a relationship (one he described as “never serious”) with Kendall Jenner, leading many to raise their eyebrows at this love triangle with these sisters in the middle of it.
Woody Allen, Soon-Yi, and Mia Farrow
Weird celebrity stories and weird love triangles have a lot of overlap. And when it comes to Woody Allen, that Venn Diagram overlap would basically be a circle.
It all started when Woody Allen started a 12-year relationship with Mia Farrow in 1979. Farrow had adopted a daughter, Soon-Yi, who was nine-years-old when Allen began dating Farrow. While Allen was dating Farrow, he was basically a father figure to Soon-Yi. And this made things that much weirder and worse when Allen began a relationship with Soon-Yi in 1991, when she was 21 and he was 56.
While Soon-Yi denied publicly that Allen was like a father to her, Allen popped a hole in this defense in a 2015 interview with NPR. There, he said, “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.” Continuing, he mused, “She flourished. It was just a good-luck thing.”
Honestly, Allen’s own words were already pretty damning. But he kept digging, admitting that when he began a relationship with a woman 35 years younger than him, “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.”
Allen gives off such big creep energy here that it’s almost impossible to watch his movies and not think about the weirdness!
Allen married Soon-Yi in 1997, and they are still together 30 years later. They even have two adopted daughters of their own.
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