The sitcom Friends dominated 90s television with audiences falling in love with the quirky relationships and daily lives of Rachel, Ross, Monica, Phoebe, Chandler, and Joey. The actors became very well-known, and so did their off-screen love lives and behind-the-scenes crushes.
From Courtney Cox dating Michael Keaton to Jennifer Aniston and David Schwimmer having a real Ross and Rachel crush on one another, here are some of the Friends casts’ former flings.
Jennifer Aniston & Brad Pitt
One of the more high-profile couples to ever grace the red carpets of Hollywood was Jennifer Aniston and Brad Pitt. For years, the two were the “it couple,” with Brad even guest-starring on Friends.
But their romance didn’t last, and the two wound up having a very public and very messy divorce in 2005, splitting the country into Team Jen or Team Angelina. After years of not speaking to one another, the two have finally put aside their differences and are friends.
Courteney Cox & Michael Keaton
Courteney Cox has gone on record saying her nearly six-year relationship with Batman star Michael Keaton was arguably one of the most important in her life. The two met through a mutual friend in 1989, and sparks flew almost immediately.
Their first date was actually very casual. According to Cox, “We talked for five hours. We talked about our dream homes—the great ones we’d seen and the kind we’d like to build ourselves.”
Matt Le Blanc & Missy McKnight
While Joey is a shameless woman-loving goofball on Friends, Matt Le Blanc was the opposite and actually settled down. The actor met model Missy McKnight back in 1997 through her friend, Lou Diamond Phillips.
The two hit it off, and Le Blanc wound up proposing the Mcknight a year later. They were wed in 2003 and had a daughter together in 2004. Unfortunately, their love didn’t last, and they divorced in 2006.
Lisa Kudrow & Conan O’Brien
Even before people knew her as Phoebe on Friends, Lisa Kudrow was dating fairly famous people. And one of those people just so happened to be late-night talk show host Conan O’Brien. Apparently, the two met at an improv class and hit it off!
According to Kudrow, “He was really smart, really funny, and he thought I was funny.” The two dated for a short time before finding out that they were better off being friends.
David Schwimmer & Natalie Imbruglia
While David Schwimmer was the geeky guy who had trouble talking to girls on Friends, he didn’t seem to have too much trouble in real life. From 1995 to 1996, he was in a relationship with Aussie singer Natalie Imbruglia.
There isn’t much in the media regarding their romance, but the “Torn” singer remembers it as a happy relationship. The two went their separate ways after a year of dating, and, no, it wasn’t just a break.
Jennifer Aniston & David Schwimmer
During the 2021 Friends: Reunion, David Schwimmer and Jennifer Aniston admitted that they almost had a real-life Ross and Rachel relationship! Behind the scenes of the sitcom, the two stars had a major crush on one another.
During the reunion, Schimmer said, “At some point, we were crushing hard on each other,” Schwimmer admitted. “But it was like two ships passing because one of us was always in a relationship, and we never crossed that boundary. We respected that.”
Courteney Cox & David Arquette
Courteney Cox and David Arquette met on the set of the 1996 film Scream. To say it was love at first sight would be lying. Arquette has even said that he had to trick the Friends star into dating him!
Well, tricking her obviously worked because they wed in 1999 and stayed married for a solid 11 years and had a daughter together, Coco. The two divorced in 2013; Arquette’s immaturity was taking a toll on Cox’s sanity.
Matthew Perry & Lauren Graham
Gilmore Girl and Friends fans were most likely very excited when the media got wind of this strange crossover relationship between Matthew Perry and Lauren Graham. First meeting at a party and exchanging a few flirty comments, the two were thought to be in a relationship.
At least, that’s what the tabloids wanted the public to think. As it turns out, the two never took their relationship further than flirting, much to fans dismay.
Matt Le Blanc & Andrea Anders
After his divorce from ex-wife Missy McKnight, Matt Le Blanc began dating Andrea Anders. The two met on Le Blanc’s Friends spin-off series Joey, quickly beginning a relationship and going public with their romance in 2006.
The two actors were together until 2012 before they decided to go their separate ways. It’s rumored that their break-up was due to Le Blanc channeling too much of his inner-Joey and having wandering eyes.
Lisa Kudrow & Michel Stern
The Friends star first met French advertising executive Michel Stern in 1980, when he was dating her roommate. As fate would have it, though, Kudrow and Stern were meant to be. The two began dating in the early 90s and eventually got married in 1995.
The couple is a Hollywood love story for the ages, as they’ve been happily married for over 23 years. They also have a son together who, as of 2021, is a college graduate!
David Schwimmer & Zoe Buckman
In 2007, David Schwimmer met Zoe Buckman while she was serving him at Cuckoo Club in London’s West End. Soon after their initial meeting, the two began dating. They fell so hard that Zoe wound up moving from London to the United States just to be with the Friends actor.
The actor proposed in 2010 and the wedding ceremony took place only months later. Unfortunately, they wound up getting divorced seven years later.
Courteney Cox & Johnny McDaid
The relationship between Courteney Cox and Snow Patrol singer Johnny McDaid has had its ups and downs, to say the least. They first got together in 2013, not long after Cox’s divorce with ex-husband David Arquette.
But with Cox wanting to stay in California and McDaid wanting to go back home to Ireland, their relationship hit a roadblock. The two didn’t stay broken up for long, though. As of 2021, they are stronger than ever.
Matthew Perry & Heather Graham
As Chandler always seemed to have dating issues on Friends, so too does Matthew Perry in real life. It doesn’t seem as though the media can get a lock on any of his “real” relationships outside of the 90s and late 2010s!
In 2003, it was rumored that he was dating actress Heather Graham. Since there is hardly any news on the two as a couple, it’s safe to say their romance wasn’t meant to be.
James Michael Tyler & Barbara Chadsey
Gunther didn’t really have much luck in the love department on Friends, crushing over Rachel for season after season without anything to show for it. Actor James Michael Taylor seemed to have had better luck, though. At least, for some time.
He married Barbara Chadsey in 1995, but they wound up separating some years later, in 2003. But it wasn’t until 2014 that their divorce was finalized. It looks like neither Gunther nor Tyler can catch a break in the love department.
Jennifer Aniston & Vince Vaughn
Was it a rebound or a fling because they just so happened to be in an on-screen relationship filming The Break-up? Who knows. But Jennifer Aniston and Vince Vaughn had quite a high-profile relationship for a solid year.
From 2005-2006, the two were followed around by the paparazzi, showing off their romance for all to see. Interestingly, Vaughn never openly admitted to being in a relationship with the Friends star, telling David Letterman, “I think she’s great, but I just don’t discuss whether we are [a couple].”
Maggie Wheeler & Daniel Wheeler
Fans might remember Maggie Wheeler as Chandler’s obnoxious, nasally ex-girlfriend Janice. And oh…my…god, who would believe that woman has actually been married to the same man since 1990.
Maggie and Daniel Wheeler married in October of 1990. The two are a bit private about their lives, but it seems as though they are still going very strong, even decades later. They also have two daughters together and love creating art, her with acting and music and him with sculpting.
Matthew Perry & Lizzy Caplan
Matthew Perry met Mean Girls star Lizzy Caplan in 2006. From there, the two embarked on quite the relationship. Very private in their lives, the two were rarely photographed with one another.
Even so, Perry and Caplan were seen out together, making it very clear that they were in a relationship. This went on until 2012. It’s rumored that the two broke things off because Perry wasn’t ready to get married.
Jennifer Aniston & John Mayer
After meeting at an Oscars after-party, Friends actress Jennifer Aniston began dating singer John Mayer. The two were only together from 2008-2009 but, boy, was it one wild ride of a relationship.
The two went through a highly publicized split and fans of the couple didn’t really know what to believe. According to an interview Aniston did with Vogue, “There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that’s where it is.”
Bruce Willis & Demi Moore
Fans might remember Bruce Willis as the very attractive older man Rachel dated, Paul Stevens. In real life, he was in a very public relationship with actress Demi Moore. The two married back in 1987 in a very un-Hollywood impromptu Vegas wedding.
The two had their first child, a daughter named Rumer, within the first year of their marriage. Three children later, their love fizzled out, and the two divorced in 2000.
George Clooney & Amal Clooney
Fans of Friends might remember George Clooney’s cameo appearance as Dr. Michael Mitchell in “The One With Two Parts, Part 2,” a spoof on his ER character. While Dr. Mitchell went on a double-date with Rachel and Monica, he never dated his co-stars.
His love was reserved for human rights lawyer Amal Alamuddin. The two were engaged in 2014 and have been happily married since that year. They have twins together, a son and a daughter.