Hollywood Love Squares: Breaking Down the Very Small World of A-List Romances

See if you can keep them all straight.

By Seija Rankin May 16, 2017 1:00 PMTags

These are people who could choose anyone. There is no such thing as winning someone over when you're a famous actor or singer. And yet, time and time again, they all wind up dating the same people. 

Not that you could fault them: The life of a celebrity all but rules out romantic relationships with civilians so the dating pool is smaller than it seems. So small that there exists in Hollywood a phenomenon we've dubbed The Love Square. We regular people are well aware of the love triangle, in which three people are romantically linked in some way or another, but when you go to the world's most exclusive surrogate high school, the geometry gets even more complicated. 

Miranda Kerr & Orlando Bloom + Orlando Bloom & Selena Gomez + Selena Gomez & Justin Bieber + Justin Bieber & Miranda Kerr

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This love square revealed itself thanks to a very salacious evening outing in Ibiza, when Orlando Bloom may or may not have taken a swing at Justin Bieber. Everyone is well aware of Bloom's history with Miranda Kerr—they were married for three years and have an adorable son to prove it—but the rumor mill started flying that Orlando got prickly over a possible past with his ex and the "Love Yourself" singer. As far as we know they just got a little cozy during a long-ago Victoria's Secret fashion show, but Bieber did post an ill-advised Instagram of Kerr (that he quickly deleted). 

Then to make things even more complicated, after Bieber and singer Selena Gomez's breakup (one of many, if we're being honest here), she started getting pretty cozy with Mr. Bloom. They share a manager, so that could easily explain the odd-at-first hangout sessions in Las Vegas. Does it explain their cozy photos together and occasional late night spottings? Not so much. 

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Selena Gomez's Best Looks

Kendall Jenner & Jordan Clarkson + Jordan Clarkson & Chanel Iman + Chanel Iman & A$AP Rocky + A$AP Rocky & Kendall Jenner

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Kendall Jenner denies relationships for a living—or at the very least, her M.O. is to never acknowledge whether she's actually dating someone. But that doesn't stop the public from putting two and two together a whole heck of a lot. First up is Los Angeles Lakers player Clarkson, who was the subject of many a Jenner rumor after being caught on dates with her time and time again. 

Clarkson also dated model Chanel Iman—the couple broke up in early 2016—who was previously in a long term relationship with rapper A$AP Rocky. That brings us to today. Or, technically, that brings us to the first Monday in May when, after what's felt like years of teasing out their relationship, A$AP and Jenner were caught in a very monogamous canoodle at the Met Ball. 

Cameron Diaz & Benji Madden + Benji Madden & Joel Madden + Joel Madden & Nicole Richie + Nicole Richie & Cameron Diaz

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We're getting creative with this square, guys! But Hollywood is nothing if not creative. Plus, we think that twin brothers and best friends totally count as significant relationships. As the world at large is well aware, Diaz and one half of the Madden twin brothers are now very happily married. The other half of the Madden twin brothers is married to Nicole Richie, and Richie and Diaz just so happen to be BFFs. The result is quite possibly the cutest little familial square-slash-couples retreat we could ever imagine. We're not jealous, you are. 

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Famously Unmarried Celeb Couples

Jennifer Lopez & Drake + Drake & Madonna + Madonna & Alex Rodriguez + Alex Rodriguez & Jennifer Lopez

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Remember that month that Drake and JLo were dating? Us, too. And remember that five minutes that Drake made out with Madonna at Coachella and made the Internet explode? Us, too. More substantially, despite the fact that they were never openly talkative about it, Madonna seemed to be together with ARod for most of 2008. Bringing it full circle is ARod's current love affair with JLo that we just can't get enough of

Paris Hilton & Stavros Niarchos + Stavros Niarchos & Mary-Kate Olsen + Mary-Kate Olsen & David Katzenberg + David Katzenberg & Nicky Hilton

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Who would have ever thought that the Hiltons and the Olsens would have so much in common? Well, the aughts were an odd time for Young Hollywood. Stavros Niarchos, a Greek shipping heir, was one of the dating pool's hottest commodities. He dated one Paris, she being the Queen of the club-going set at the time, and one Mary-Kate. The slightly younger Olsen twin (Ashley was born two minutes earlier, guys!) also spent a good portion of time getting cozy with David Katzenberg (his father is a film industry legend and the co-founder of DreamWorks Animation), who went on to date Paris' sister Nicky. And with that, Paris and Mary-Kate never did anything similar ever again. 

Justin Timberlake & Cameron Diaz + Cameron Diaz & Jared Leto + Jared Leto & Scarlett Johansson + Scarlett Johansson & Justin Timberlake

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Cover your ears, Jessica Biel! JT famously dated Cameron Diaz for over three years together in the early 2000's—and yes, this was well before they reunited onscreen to star in Bad Teacher. Many millennials will probably be unaware (and others have probably forgotten) that Diaz was engaged to Jared Leto after they started dating back in the dear old '90s. Leto briefly dated Scarlett Johansson in 2004, and although nothing was ever confirmed in the hard-and-fast sense, ScarJo and JT were the subject of many a coupledom rumor. And frankly, all of those pairings make perfect sense to us.