20 Celebs Who Decided To Date The Ex Of Their Best Friend, For Better Or Worse
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It's not uncommon for celebs to date around, and since their circles are carefully curated, there are definitely some chances for overlap.
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That doesn't mean there aren't hurt feelings or straight-up anger over the decisions though.
There are just some rules that aren't meant to be broken.
Generally speaking, no one's happy when their friend is dating their ex. Even if there aren't ~feelings~, there are still plenty of opportunities for uncomfortable situations.
Despite that, some celebs have dared to share.
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There are more than a few celebrities out there who have dated someone after a really close friend of theirs has. The situations have ranged from harmless to scandalous.
1.Selena Gomez dated Taylor Lautner before he and her bestie, Taylor Swift, hit it off.
Selena Gomez and Taylor Lautner met while they both happened to be in Vancouver shooting movies in 2009. Selena was reportedly into it, only to be crushed when after a few dates, Taylor ghosted her. Reports indicate his dad thought being single would be better for his career at the time, though Selena and Taylor have denied things ever having been romantic between them.
Taylor squared became a thing just a few months later.
You may remember that Taylor Lautner and Taylor Swift played a high school couple who were completely obsessed with each other. Reportedly they started feeling the same offscreen during filming. Things between them lasted for a few months before they called it quits, but it never seemed to present a problem between the two besties, whose friendship is as strong as ever today.
2.Shawn Mendes dated Hailey Baldwin in between her relationships with Justin Bieber.
You likely know that Hailey Baldwin and Justin Bieber are happily married today, but did you know they dated when they were younger? The two were together for some months in 2015, but went their separate ways until reuniting in 2018.
The year before their reunion, Hailey was linked to Justin's fellow Canadian pop star, Shawn.
Justin was supportive of Shawn's early career, so dating Hailey definitely resulted in some shade between the two.
3.Lindsay Lohan and Hilary Duff's friendship wouldn't survive their shared romantic interest.
Young love is certainly fickle, and this millennial love triangle proves it. Aaron Carter began dating Hilary Duff after appearing on Lizzie McGuire. They were together for about a year and a half before his eyes started wandering.
Aaron got to know Lindsay before returning to Hilary.
Lindsay was into Aaron, and for a moment it looked like they'd be the new teen "it couple." Things fizzled out pretty quickly, however, which sent Aaron marching back to Hilary.
Nina Dobrev dated Ian Somerhalder during their onscreen love affair on The Vampire Diaries.
Nina Dobrev and Ian Somerhalder had a pretty steamy relationship on TVD. The real-life thing was just as hot and saw the two as a serious item from 2009 to 2013.
Ian and Nikki Reed gave it a go afterward, and the rest was history.
Ian and Nikki started dating in 2014. It might not have been so awkward if Nikki and Nina weren't friends. Things could have been weird, but Nina seemed to accept it, even when the couple tied the knot in 2017. They're still friends to this day.
4.Drew Barrymore shares something more than a godfather with bestie Gwyneth Paltrow.
Gwyneth and Drew have been close for pretty much all of their lives. They share a godfather in Steven Spielberg, who helped both the starlets start their mega-watt careers. The two longtime friends have also been tied to the same leading man.
Both Drew and Gwyneth dated Luke Wilson.
Drew and Luke dated for two years from 1997 to 1999 before calling it quits. It was an amicable breakup, however, as evidenced by Drew casting Luke in The Royal Tenenbaums. During filming, he struck something up with his onscreen sibling, Gwyneth, though the two ended it by the end of 2001.
5.Gwyneth would later find herself becoming friends with someone who dated another ex of hers.
Before Jennifer Aniston and Brad Pitt's time as Hollywood's golden couple, he was half of another hot couple. He dated Gwyneth from 1994 to 1997, and they were even engaged during the last year of the relationship.
Friends set Jennifer and Brad up on a blind date by their agents.
Jennifer first met Brad around the time that he started dating Gwyneth. The two met because their agents were friends. Later, their agents would think to set them up on a blind date, leading to a five-year-long marriage. Though things didn't work out, they remain friends, as he does with Gwyneth. The sweet friendship between Jennifer and Gwyneth was an added bonus from the situtation.
6.Even Jennifer Aniston and Courteney Cox couldn't avoid dating the same guy.
The Friends alums have been closer than close ever since they portrayed roommates. You didn't really see Monica and Rachel going after the same guys, but Courteney and Jennifer did have an unlikely boyfriend in common.
Both actors dated Counting Crows frontman Adam Duritz.
Jennifer first met Adam in 1995 after being set up by mutual friends. "It didn’t last very long, but she’s a nice girl," he told ET Canada. Later, he'd be linked to Courteney after she starred in the band's 1997 video for " A Long December." It never seemed to cause a problem for the two buddies, and Adam has nothing but fond memories of both.
7.Many believed that dating the same guy was the beginning of the end of Taylor Swift and Katy Perry's friendship.
It may be hard to remember the days that Taylor Swift and Katy Perry were friends, but in a 2009 world, such was the case. At the time, many thought it was John Mayer that came between the two friends. Taylor dated John from 2009 to 2010.
Katy dating John on-and-off for two years wasn't the problem between them.
It's easy for Hollywood to blame a man for coming between two women. Both Taylor and Katy have refuted that's what started the, ahem, bad blood between them. After some passive-aggressive jabs at each other, both ladies have resolved to behave more civil in recent years.
8.The TomKat-Jamie Foxx love triangle was one that no one saw coming.
Tom Cruise and Jamie Foxx became close after teaming up on Collateral. At the time, Tom was newly married to Katie Holmes. The two ended up getting divorced in 2012.
Katie and Jamie kept an incredibly low-profile dating afterward.
Jamie and Katie were first linked in 2013, though rumors about their romance didn't really pick up speed until 2015. Though they were known to be a couple, the two only started making public appearances together in 2019, shortly before their breakup.
9.Kristen Wiig isn't just friends with Drew Barrymore; she's played her on Saturday Night Live.
Drew dated The Strokes' drummer, Fabrizio Moretti, for five years from 2003 to 2007. It's a pretty long-term relationship, so you'd almost understand it if she was mad when her pal, Kristen Wiig, was linked to him in 2011.
Drew just rolled with the punches, and it made their friendship stronger.
"It all seems so wacky and incestuous, but that's kind of how life works," Drew told Allure of the pairing. "It seems fitting that they would find each other. I was like, 'Right, of course, that makes perfect sense.'" Kristen and Fabrizio would go on to call it quits in 2013.
10.Cameron Diaz shares one ex with two friends and is totally breezy about it.
Everyone's always loved Cameron Diaz's easy-going spirit, and her way of handling friends dating her ex just makes us love her even more. It all started when her buddy, Kate Hudson, started dating Alex Rodriguez in 2009. Their love affair only lasted until shortly after his World Series win that fall.
11.Then Cameron dated him drama-free and didn't mind when another friend did the same.
Cameron and A-Rod dated for about a year from 2010 to 2011. Six years later, Jennifer Lopez and Alex began dating. Cameron was totally cool with the decision, as evidenced by her and Jennifer working together on What to Expect When You're Expecting.
12.Cameron and Jennifer also have another ex in common.
That's right. Both these lovely ladies have dated Sean "P. Diddy " Combs. J.Lo and Diddy were a power couple from 1999 to 2001. Cameron was first linked to Diddy in 2008, and again in 2012.
13.Cameron and Kate would also end up with another mutual ex.
Cameron was famously with Justin Timberlake from 2003 to 2007. Interestingly, it was right after that breakup that he was linked to Kate Hudson, which reportedly gave Cameron the gall to strike things up with A-Rod.
14.Nick Lachey and Nick Cannon's friendship became stronger after they decided the same woman wasn't right for either of them.
Though Nick Lachey and Nick Cannon knew each other for some time, they were more like acquaintances at first. That changed thanks to a woman named Kim Kardashian.
Lachey was spotted with Kim shortly after his divorce from Jessica Simpson.
Nick hasn't ever spoken highly of his time with Kim in 2006, however, slamming her as an attention seeker. He even claimed that she would tip paparazzi off to where they were hanging out. Nick Cannon claimed his experience with Kim was similar. They dated later the same year but broke up when her adult home movie was leaked online.
15.Kate Beckinsale and Sarah Silverman became friends because of the man they had in common.
Kate Beckinsale spent eight years with actor Michael Sheen from 1995 to 2003, during which the couple had a baby together. Things were a little tense between the two immediately post-breakup, but quickly came to an amicable place.
Sarah dated Michael from 2014 to 2018.
She even announced their breakup on his birthday, in typical comedian fashion. Her chosen shoulder to cry on? Kate, who sent her M&M's with photos of the two together to help her get through.
16.Adam Levine couldn't get between these Victoria's Secret angels/besties.
These days, everyone knows Maroon 5 frontman Adam Levine is married to former Victoria's Secret model Behati Prinsloo. The two share two very cute daughters and seem totally happy and in love. Behati wasn't Adam's first angel, however.
Before Behati, Adam dated angel Anne Vyalitsyna.
Anne and Behati both came up in the Victoria's Secret world at the same time, so the two were very close-knit. That's why Anne initially had a tough time when Behati started dating Adam in May 2012, shortly after she and Adam broke up. Behati and Adam announced their engagement the following year, and Anne was supportive.
17.Heather Locklear and Denise Richards' friendship also didn't survive a man-related fallout.
Heather Locklear was married to Richie Sambora from 1994 to 2007. Obviously, everyone in Heather's orbit knew how in love the two were and how heartbroken she was at their split. Which is why their mutual friends were shocked to see one of Heather's closest friends, Denise Richards, start dating Richie shortly after the divorce.
Denise insisted that hooking up with Richie was never the intention.
Denise, for her part, says that she and Heather's friendship was fractured way before she became involved with Richie. She also claims the two came together, initially, to support each other as they both navigated divorces (Richards from Charlie Sheen) and parents with illnesses. The romance was short-lived, and the friendship never recovered.
18.Shania Twain and her best friend ended up swapping husbands, and it's just as scandalous as it sounds.
Shania Twain married record producer Robert John "Mutt" Lange in 1993, after working together on some of her early hits. During their marriage, Shania hired Marie-Anne Thiébaud as a house manager. Shania and Mutt became close with Marie-Anne and her husband, Frédéric Thiébaud.
Mutt asked for a divorce after 14 years of marriage for what seemed like no reason.
Shania wouldn't learn until later that he and Marie-Anne were already involved. Frédéric found out about the affair and told Shania, who was understandably crushed. The two leaned on each other, and although a romance was the furthest thing from Shania's mind, the two eventually ended up together. They began dating in 2009 and married the next year and are happy and in love to this day.
19.George Harrison and Eric Clapton never imagined they'd love the same woman.
The two prolific musicians were both at amazing points in their career and great friends when Eric found himself falling for George's wife at the time, Pattie Boyd. Eric poured his feelings into music, never dreaming of betraying his friend. Fate had different plans for all three of them.
In the early 1970s, George and Pattie split up.
Eric was isolated by his struggles with addiction at the time. Once he got clean, he found his way to Pattie. George gave the relationship his blessing and was even there when Eric and Pattie tied the knot in 1979. They'd remain married for a decade.
20.Debbie Reynolds and Elizabeth Taylor briefly fell out over Eddie Fisher.
Eddie Fisher originally set out to comfort his friend, Elizabeth Taylor, after the death of her husband, Mike Todd. The increased time together resulted in an affair despite his marriage to Elizabeth's once-neighbor and longtime friend, Debbie Reynolds.
The ladies were forced to talk it out years later when they bumped into each other on a cruise.
Elizabeth and Eddie went on to get married, though they divorced in 1964. Two years later, Elizabeth and Debbie ended up on the same cruise ship and talked out their differences. They were able to mend their friendship and remained friends until Elizabeth's death in 2011.
