16 Celebs Who Dated Their Friend’s Ex

There are certain unspoken codes of loyalty between friends, and a big one has to do with their love lives — even when we're talking about celebrity couples. In general, a friend's ex is always off-limits, and there are very few exceptions to this rule. But at the same time, there's no accounting for who you might fall in love with. And just as some of us find ourselves in rather sticky situations in our own romantic lives, so do our favorite stars. More celebs have actually dated each other's exes than you might think — even longtime celebrity friends.

From Jennifer Lopez and Cameron Diaz to Jennifer Aniston and Courteney Cox, surprisingly enough there have been a lot of pals who have been totally cool about sharing an ex with a friend — and of course there are also former friends who felt decidedly less cool about the whole thing.

Read on about celeb friends who happened to date the same person. Even though it definitely had to be awkward for some of them, many of these friendships came out on the other side unscathed.

Gwyneth Paltrow & Drew Barrymore

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It never seemed to hurt their friendship (even to this day), but Gwyneth Paltrow and Drew Barrymore both dated Luke Wilson. Drew and Luke were together first, dating after they starred in Home Fries together only to break up in 1999. A few years later, Gwyneth dated Luke for a year after meeting on the set of The Royal Tenenbaums.

Nina Dobrev, Ian Somerhalder, & Nikki Reed

Things could have been real awkward after Vampire Diaries stars Nina Dobrev and Ian Somerhalder broke up, only for him to date (and eventually marry) Nina's friend and fellow actress Nikki Reed. But instead, they've remained incredibly cool about it, and all three of them have even hung out together.

Cameron Diaz & Britney Spears

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Cameron Diaz and Britney Spears have always had a mutual admiration for each other, and that didn't change just because they share an ex. They both had pretty serious (and high-profile) relationships with Justin Timberlake in the past, but now Cameron and Justin are happily married to Benji Madden and Jessica Biel, respectively, while Britney is engaged to Sam Asghari.

Katy Perry & Taylor Swift

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Yes, there's been a lot of drama here, but in the end, these two kissed and made up. Katy Perry and Taylor Swift both dated John Mayer — and had a totally unrelated feud that played out pretty publicly when Taylor's single "Bad Blood" was aimed at Katy. But they got over it, and Taylor even invited Katy to appear in her music video for "You Need To Calm Down," symbolically hugging her at the end.

Tom Cruise & Jamie Foxx

Tom Cruise's marriage to Katie Holmes didn't last, and neither did Jamie Foxx's very low-key relationship with her years after Tom and Katie divorced — but hopefully, the guys' friendship is still going strong now that she's out of both of their lives. Here, all three of them were pictured together at a football game in 2006.

Kate Beckinsale & Sarah Silverman

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Sarah Silverman and Kate Beckinsale have a shared ex in Michael Sheen, but they've never let it bother them. In fact, after Sarah broke up with Michael, she even revealed that Kate had given her M&Ms with photos of her and Michael on them for Christmas before they'd broken up — another thing they could joke about and bond over.

Jennifer Aniston & Courteney Cox

Jennifer Aniston and Courteney Cox's friendship that started on the set of Friends is legendary at this point — and not even stepping out with the same guy could get in the way of it. In the '90s, they both dated Counting Crows singer Adam Duritz, who told Men's Health that they were both "nice girls."

Lance Armstrong & Owen Wilson

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Though neither of their relationships ended up working out, friends Lance Armstrong and Owen Wilson both dated Kate Hudson. Lance and Kate were together for less than a year, whereas she and Owen dated on and off for a couple of years after meeting on the set of You, Me, and Dupree.

Taylor Swift & Selena Gomez

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Selena Gomez and Taylor Swift are so inseparable that it doesn't seem to matter to either of them that they both dated Taylor Lautner. Selena dated the Twilight star briefly in 2009, just months after Taylor had dated him. Later, Taylor would write the song "Back to December" about him.

Nikki Reed & Kristen Stewart

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Here's another example of a vampire-themed love triangle involving Nikki Reed! Both Nikki and Kristen Stewart ended up dating Robert Pattinson after filming Twilight, but as we know now, neither of those romantic relationships worked out — and despite rumors at the time, Nikki has even denied ever dating Rob in the first place. Fortunately, their friendship survived it all.

Cameron Diaz & Kate Hudson

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Long before his ill-fated engagement to Jennifer Lopez, Alex Rodriguez dated both Cameron Diaz and Kate Hudson, who just so happened to be friends. Alex and Cameron dated for a little over a year back in 2011, while he and Kate were together for about as long from 2008 to 2009.

Drew Barrymore & Kristen Wiig

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Both Kristen Wiig and Drew Barrymore dated Fabrizio Moretti of the Strokes, and not only are they cool about it, but Drew even totally understood why he and her friend would be good together.

"It all seems so wacky and incestuous, but that's kind of how life works," Drew told Allure in 2012. "It seems fitting that they would find each other. I was like, 'Right, of course, that makes perfect sense.'"

Gwyneth Paltrow & Jennifer Aniston

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Not only did these ladies date the same man, but they both almost married the same man. As we know, Jennifer Aniston was married to Brad Pitt for five years before they called it quits in 2005, and Gwyneth Paltrow was with him for three years in the '90s, even getting engaged before they broke up.

Taylor Swift & Ellie Goulding

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Taylor Swift makes the list again, this time paired with friend Ellie Goulding. One of Taylor's more serious relationships was with musician Calvin Harris, and Ellie reportedly dated him too back in 2013 — around the time they were working on music together.

Nick Cannon & Nick Lachey

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Long before her marriage (and divorce from) Kanye West, Kim Kardashian had history with these pals — kind of. She briefly dated Nick Cannon in the early 2000s, and went on one date with Nick Lachey after his breakup with Jessica Simpson.

Cameron Diaz & Jennifer Lopez

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Not only did Cameron Diaz and Jennifer Lopez both date A-Rod, but they also both dated Diddy. J.Lo was first, dating him in 1999, and then Cameron dated him for four years starting in 2008. The friends went on to film What To Expect When You're Expecting together, totally drama-free.