Celebs Who Dated Before They Were Famous (2024)

Drew Barrymore and Corey Feldman

After starring in an episode ofCBS Schoolbreak Specialtogether, 14-year-old Drew Barrymore and 18-year-old Corey Feldman briefly dated. This wasn't the first time the couple got together, though. In Feldman's memoirCoreyography, he wrote that the two went on a first date in 1985 when Barrymore was ten, and he was 14. They were set up by his manager at the time—who also happened to be Barrymore's mom.

In the end, he said the two broke up in 1989, due to his heavy drug use while she was trying to get sober.

Jennifer Garner and Scott Foley

Before she went on to have the lead inAlias, Jennifer Garner played Scott Foley's girlfriend onFelicityfor two-episodes in 1998 and ended up falling in love with her co-star.

The couple got married in 2000, but split up in 2003. As for why they broke up? Garner believes she and Foley "were the victims of Hollywood."

"Everything is speeded up here—it is a fast-lane life, and if something is not working, it is considered best to end it without much thought,"she toldInStyle."If we lived where I was brought up [West Virginia], we would probably still be together."

Leighton Meester and Sebastian Stan

Before Sebastian Stan made his way into the Marvel Universe withCaptain America: The First Avenger, the couple dated for two years. It's another on-set romance we totally missed, or perhaps don't remember. Either way, the two started dating in 2008 when Leighton Meester, who was killing it as Blair onGossip Girl, met Stan, who played her on-screen fling, Carter Baizen.

Meester hinted about the breakuptoSeventeen,saying, "I've only had one experience where it was really hard, and I was really sad when it ended, but that's what taught me a lot about myself and love and life–and that's good."

Sarah Jessica Parker and Robert Downey Jr.

Before Robert Downey Jr. suited up as Iron Man and Sarah Jessica Parker walked the streets of Manhattan as Carrie Bradshaw, these lovebirds dated for eight years. The pair met on the set of the 1984 dramaFirstbornwhen they were 18 years old. They shortly moved in together in a house in Los Angeles just two months after dating.

They broke things off due to Downey Jr's battles with addiction. "She provided me a home and understanding. She tried to help me. She was so miffed when I didn't get my act together; hetoldParade."I was in love with Sarah Jessica...and love clearly was not enough."

Jennifer Love Hewitt and Will Friedle

After being introduced by a friend and playing BFFs on the set of the 1997 film,Trojan War, the two 18 year olds hit it off. Hewitt would go on to guest-star as a love interest for Friedle's character Eric inBoy Meets Worldbefore Love Hewitt became known for her role inI Know What You Did Last Summer.

Jennifer Grey and Matthew Broderick

Before Jennifer Grey would become a household name for her role inDirty Dancing, she fell in love with co-star Matthew Broderick on the set ofFerris Bueller's Day Off. Until the summer of 1987, the couple's relationship was a well-kept secret until they got in a head-on crash off the coast of Ireland that ended up killing two people.

The pair broke up afterwards. Greyadmitted toPeopleshe was never the same after the incident: "The impact was emotional and physical," she said. "My body was never the same. My head was never the same. My ambition was never the same."

Busy Philipps and Colin Hanks

Before she was onFreaks & Geeksand he was onRoswell, Busy Phillips and Colin Hanks both attended Loyola Marymount University. They dated for a long time—long enough to be with each other when they landed their first roles, and are still friends to this day. “He was my college boyfriend!” Philipps said onLive with Kelly. "We met when I was 18 and Colin was 19...We are very very close friends now—his wife and I are tight, he and my husband hang out. We go on vacation together."

David Gallagher and Megan Fox

At the time, he was the teen hearthrob from7th Heavenand she had two film roles to her name, including the 2001 Mary-Kate and Ashley Olsen film,Holiday in the Sun. They were inseparable for the year they dated in 2003.

Matthew Morrison and Lea Michele

Matthew Morrison dated his future co-star Lea Michele during their time on the Broadway scene, long before FOX's hit musical showGleewas even a thing. Rumors swirled about their relationship once the series aired, but the actors denied it and attributed their on-screen chemistry to their long-time friendship.

Michele came clean about the romance in her 2014 autobiography, Brunette Ambition. "When we shot the pilot, I met Cory Monteith, Kevin McHale, Amber Riley, and Chris Colfer for the first time,” Michelewrotein the book. “I had worked on Broadway with Jenna Ushkowitz and Matthew Morrison before. Matt had been a friend of mine for years, and in fact we’d actually dated back in the day for a Broadway beat.”

Jessica Biel and Chris Evans

These two dated on-and-off from 2001 to 2005. She was already fairly well-known for7th Heaven, but he'd only had bit parts on a few mini-series and TV movies when they hooked up. Needless to say, these two have come very far since they dated.

Matthew Morrison and Kristen Bell

The duo paired up when they were students at New York University, long before Bell becameVeronica Marsand Morrison made a name for himself on Broadway and in shows likeGlee.Bell revealed in an interview withUs Weeklyin 2010: "We actually dated very briefly. So I'll have to say maybe Matt Morrison is my favorite part ofGleefor various reasons."

Denise Richards and Paul Walker

One of the late actor's first gigs was in the 1994 science comedyTammy and the T-Rex. The movie may not have been a hit (and that's putting it nicely), but Walker did hit it off spectacularly with Denise Richards, his co-star in the film. The ridiculously good-looking couple dated shortly after the film was released before going their separate ways.

Michael Keaton and Courteney Cox

The early-to-mid '80s brought Michael Keaton to Hollywood, and he began dating a then-unknown aspiring actress named Courteney Cox. She'd done a recurring role onFamily Ties, but her iconic time as Monica onFriendswas still a few years away when she and Keaton started dating in 1989. They were together for six years before they split in 1995, a year afterFriendsblew up.

George Clooney and Kelly Preston

It seems like the '80s were a time when future A-listers were all hanging out and dating each other, like George Clooney and the late Kelly Preston before finding lasting love with their respective spouses (Amal Clooney and John Travolta, of course). Their young romance lasted from 1987 to 1989, and they even lived together with Clooney’s beloved pet pig, Max.

Joey Lawrence and Keri Russell

Talk about hair goals! Joey Lawrence and Keri Russell were a hot item in the '90s, hitting the town together prior to Russell's days as the hate-to-love main character ofFelicity. The relationship wasn't without its fair share of drama, though; Russell was still involved with her on-again, off-again boyfriend Tony Lucca ofThe Mickey Mouse Clubat the time.

These two dated on and off for15 yearsbefore they got married on September 6, 1997. They met in the early 1980s at New York City's Atlantic Theater Company, and for Huffman, it was love at first sight. They bonded over a love of acting, and then Huffman "went on a campaign. He was certainly worth it," she toldThe Daily Mail.

Zooey Deschanel and Jason Schwartzman

These two started dating when they were both 19 years old, before she had her breakout role inAlmost Famousand right after he won our hearts inRushmore.Deschanel has said Schwartzman was her first "real" boyfriend. The pair broke up in 2005.

Fred Savage and Jennifer Love Hewitt

Does going on one date qualify as "dating?" If so, Fred Savage and Jennifer Love Hewittdefinitelydated, but Hewitt's unique choice of pet didn't exactly make a great first impression.

"Fred Savage was my first date," shetolda group of former child actresses (includingFull House's Jodie Sweeten and Beverley Mitchell from7th Heaven) on Facebook Live. "Because he was Fred Savage, he was able to get us in very young to the Laugh Factory, we went to a comedy show and dropped me off. And I had a pig as a pet at the time, so I never saw him again, because I had a pig as a pet and he was really creeped out. He was very sweet. I had a huge crush on him."

Reese Witherspoon and Chris O'Donnell

Today, she's the star of the big screen, and he steals the show on the small, but in 1993, these two were just kids trying to make it big in Tinsel Town. Right after his breakout appearances inSchool TiesandScent of a Woman, Chris O'Donnell dated Reese Witherspoon. She was 16 years old and just moved to Los Angeles.

Angela Bassett and Courtney B. Vance

Angela Bassett and Courtney B. Vance met in the Masters program at the Yale School of Drama in the '80s, and were friends for years before they got together romantically. They married in 1997, and welcomed twins in 2006. “He had a beautiful, beautiful girlfriend at the time, who was also in drama school with us,” Bassett remembers. “So maybe about 14 years later, our paths crossed here in Los Angeles. And I was single, he was single. And I had such an appreciation for him over those years—of his consistency, how he treated other people, of what a supporter he is, what a connector of people and ideas he is, how passionate he is.” Bassett shared withPeople. That's what a love story looks like!

Liam Neeson and Helen Mirren

This one's a shocker! TheTakenactor and the Oscar-winner dated for five years in the 1980s—after meeting on the set ofExcaliburin 1981—when she was still working to breakthrough in film and he was mostly unknown. According to Neeson, he was smitten by his co-star at first sight, and they started dating soon after filming.

"We didn't date—we lived together," Mirren confirmed during an episode ofThe Graham Norton Showin 2018. "We were a serious item for awhile."

Minka Kelly and Donald Faison

He was a star onScrubs,but at the time, she was still an up-and-coming-actress, years away from her starring role onFriday Night Lights.The couple wasn't shy about being seen in public together.

Justin Timberlake and Fergie

In 1997, before NSYNC had even released their first album, Justin Timberlake and Fergie-Ferg dated (she was a member of girl group Wild Orchid). "He was 16 and I was 23," she told Australia'sCourier Mailof her "Where is the Love" collaborator. "It was before he got real heavy with Britney." They've both since had high-profile romances, with Timberlake marrying Jessica Biel (another feature on this list!) and Fergie settling down with Josh Duhamel, who she later divorced.

Justin Timberlake and Jenna Dewan

Jenna Dewan first met Justin Timberlake when she worked as a background dancer for him after he went solo. When she appeared on Bravo'sWatch What Happens Live, Dewan spilled the tea on their short-lived romance. "We dated, not that long," Dewan shyly confessed. "We were like friends ...that dated."

In Lifetime's unauthorized Britney Spears biopicBritney Ever After, Dewan and Spears had a dance-off at a club over Timberlake—totally fictional, Dewan swears. "I really wish I could say that happened, because that would be the coolest story in the world, but it never happened."

Keira Knightley and Jamie Dornan

All the way back in the days of 2003, Knightley was a working actress, known for part inBend It Like Beckham,but far from the household name we know today. That year, she started dating Jamie Dornan, who at the time was a model for Calvin Klein and more than a decade away from starring inFifty Shades of Grey. They dated for two years and split in 2005, a year before Dornan's first film credit.

Charlie Sheen and Robin Wright

Many of Charlie Sheen's romantic relationships have been very public, but one love connection slipped under the radar: his teenage love affair with Wright. The actors were romantically involved from 1981 to 1982.

Ashton Kutcher and January Jones

Before she hit it big withMad Men, January Jones dated then up-and-coming actor Ashton Kutcher from 1998 to 2001. According to Jones, he wasn't the shining example of a model boyfriend, though:"He was not supportive of my acting," Jones toldGQin 2009. "He was like, 'I don't think you're going to be good at this.' So, f--k you!"

Tobey Macguire and Rashida Jones

Before starring as Peter Parker in the early 2000sSpider-Mantrilogy, Tobey Macguire was in a three-year relationship with Rashida Jones. After their breakup, Jones went on to discuss her changing perspective on relationships withThe Guardian. "I'm happy, but the fact that I'm not married and don't have kids—it's taken me a long time to get to a place where I actually am okay with that, where I actually don't feel like I'm some sort of loser."

The actress later found love with Vampire Weekend frontman Eza Koenig, and the couple has one child together.

Juliette Lewis and Brad Pitt

Yes, there actually was a time that Brad Pitt wasn't Hollywood royalty. In 1989, before he broke out inThelma and Louise,then-26-year-old Pitt began dating his 17-year-oldToo Young to Die?costar Juliette Lewis. Despite the age difference, the pair dated for four years before splitting up in 1993.

"It amazes me that people are still fascinated that we went out for four years. I was a teenager at the time. It’s a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous,"Lewis toldThe Daily Mailin 2010.

Lisa Kudrow and Conan O'Brien

If it weren't for Conan O'Brien, Lisa Kudrow might never have graced our screens, and for that, we thank him. The pair met in an improv comedy class and Lisa Kudrow was instantly attracted to him. The duo shared a brief romance before deciding they were better as friends. Her first improv class left her embarrassed and shy, but O'Brien encouraged Kudrow to keep going in her pursuits. And look where they both are now!

Carey Mulligan and Marcus Mumford

In a truly adorable story, Carey Mulligan and the Mumford and Sons lead singer were childhood pen pals who reconnected as adults at a party in Nashville in 2011. They married in 2012, and welcomed a daughter in 2015 and a son in 2017.

Jessica Simpson and Jensen Ackles

Though Jessica Simpson's most famous relationship played out before all of our eyes courtesy of her reality seriesNewlyweds: Nick and Jessica(who could forget that iconic "chicken of the sea" moment?), before that, Simpsondatedthe star of The CW horror fantasy seriesSupernatural. In an episode ofNewlyweds, Simpson told her then-husband Nick Lachey about the heartbreak that her first love caused her, and fans speculated that she was talking about Ackles.

Jon Hamm and Jennifer Westfeldt

These two linked up in 1997, a full four years before Westfeldt co-wrote and starred inKissing Jessica Stein, and a full decade beforeMad Menwould grace the small screen, launching Hamm into stardom. The pair split in 2015 after 18 years together.

Alanis Morissette and Ryan Reynolds

Right around the time that Ryan Reynolds really hit his stride in Hollywood as Van Wilder in the 2002 comedyNational Lampoon's Van Wilder, he started dating Alanis Morissette. The Canadian couple got engaged in 2004, but they decided to go their separate ways in 2008.

The breakup was very hard for Morissette, who later admitted that her seventh studio album,Flavors of Entanglement, was inspired by her heartbreak. “Yeah, it’s really about my grief,” the singersaidof the album. “I think the most painful, sort of suffering-oriented moments in my life [are] when I’m resisting something…If I just say, ‘It’s true. I’m unbelievably insecure, really broken, devastated,’ then I can move through it, toward the next place. But if I keep resisting it, I’ll stay there forever.”

Robin Thicke and Paula Patton

These two were the very definition of puppy love when they hooked up in the early '90s (she was 15 and he was 14). They remained together when both of their careers exploded, especially in 2013 after "Blurred Lines" came out. Sadly, they announced their split after 21 years together in 2014.

Ryan Gosling and Sandra Bullock

Ryan Gosling had only been in a few films before he was cast in the 2002 psychological thrillerMurder by Numbers.SandraBullock, though, was a household name after starring in films likeSpeed,While You Were Sleeping, andMiss Congeniality. Still, the co-stars connected on-set and went public with their relationship at the film's premiere.

Even after they split, Gosling had nothing but nice things to say about his ex. "I had two of the greatest girlfriend of all time," he said of Bullock and his other ex, Rachel McAdams. "I haven't met anybody who could top them."

Well...maybe he did; Gosling eventually met Eva Mendes, and they now have two daughters together.

Miley Cyrus and Tyler Posey

When Tyler Posey was just nine years old, he starred in a television show calledDocwith Billy Cyrus. While on set in Toronto for the medical drama, theTeen Wolfstar met the country icon's daughter, and it was puppy love at first sight.

"We were so damn young…I would get excited when we would hold hands,” he admitted toETin a 2015 interview. "She was herself at 7 years old. She knew who she was. I never met anyone like that at my age.”

Scarlett Johansson and Jack Antonoff

He's now a hit music producer and she's an ultra-famous actress, but these two dated for two years while attending the Professional Children’s School in New York City. They were even each other's prom dates! But it didn't end smoothly: “When we were in high school, Jack was absolutely obsessed with her, and she broke his heart,” a school pal toldPage Six. “They broke up shortly after graduation...She got swept up in the Hollywood scene.”

Jay Leno and Sharon Osbourne

Before she became the First Lady of Rock & Roll, Sharon Osbourne had a short affair with late night comedian, Jay Leno. They started a "flingy-wingy" (as Osbourne so cheekily called it) after meeting by chance one night in a bar.

"He came to my house and he met me and then we had a little fling. And the fling was more fling for me, and not fling enough for him," the talk show host told audiences ofThe Talk. "Because a couple of months into it, he brought around his real love of his life for me to meet, and she was lovely, and they took me to Fatburger, and they showed me around town."

Adrien Brody and Elsa Pataky

Elsa Pataky was famous for her acting in Spain, but was relatively unknown by global audiences until she played patrol officer Elena Neves in the 2011 action flickFast Five. But back in 2006, Pataky started dating Oscar-winner Brody. The actor was so enamored with his lady love that he bought her a giant castle (yes, you read correctly) in upstate New York.

"The first time I saw her I was completely spellbound," Brody gushed about his then-girlfriend toHELLO! Canada. "I told Elsa later that I was so uncomfortable because she was so beautiful and so lovely and sweet. I became very self-conscious. But I remember everything."

Neil Patrick Harris and Christine Taylor

Hey, we all need some time to figure things out! In 1997, Neil Patrick Harris (mostly known forDoogie Howser, M.D.)and Christine Taylor (who'd just appeared inA Very Brady Movie)dated for a brief period of time. "She's the coolest, nicest chick ever. She's an absolute catch. And I thought,If I'm not going to feel the super sparks with her, it probably means I'm gay,"Harris later told Howard Stern.

Oprah Winfrey and Stedman Graham

Before she became the media powerhouse that we know her as today, Oprah Winfrey started out as a small-time reporter and later anchor on the local news in Chicago. In 1986, the same year as the television debut ofThe Oprah Winfrey Show, Winfrey started dating Stedman Graham. Though the power couple have been engaged since 1992, they never went ahead with the ceremony, and Winfrey believes that not getting married has been the secret to their success.

She explained her reasoning in a 2017 interview withVogue:"The only time I brought [marriage] up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’ And the answer is: ‘We wouldn’t be together. We would not have stayed together, because marriage requires a different way of being in this world.'"

Katy Perry and Matthew Thiessen

Katy Perry's roots in the Christian music world led her to date Reliant K frontman Matthew Thiessen, and the two were inseparable for three years. While they were together, Perry (then known by her real last name, Hudson) was often spotted rocking out and evenstage divingat Reliant K concerts.

The two went their separate ways in 2005, but according to Thiessen, there's no bad blood. "We're not too close, but yeah, she's a great person," hesaidof his ex. "So yeah, while I was working on this Owl City stuff, she was hitting the cover ofCosmo. And then, all of a sudden, it's a couple months later and he's charting and radio success and all this stuff. And I'm like, that's really cool. Two of my friends have just become really popular in a short amount of time."

Sterling K. Brown and Ryan Michelle Bathe

The world fell in love with Sterling K. Brown when he played the best husband/dad ever in the NBC family drama,This Is Us, but he and his wife made it official long before either of them found fame.

The adorable couple met while attending Stanford University in 1998. Because they were both studying acting and performing in campus productions together, Brown and Ryan Michelle Bathe's fated meeting was inevitable, but their connection was much deeper than that.

"We found out that we were both from St. Louis. We didn't know that we were both from St. Louis, like, our parents went to rival high schools," Brown explained toET. "We were born in the same hospital. Like, we were friends."

Ryan Reynolds and Melissa Joan-Hart

When Melissa Joan-Hart started filming the pilot of theSabrina the Teenage Witchmovie, she met a young Ryan Reynolds on set, and a ~love spell~ was cast. The two started dating, but things were...complicated, to say the least.

"He was very sweet. I had a boyfriend at the time but we were smitten and cute and he was adorable," Joan-Hart told Australian TV showStudio 10. "He was a really, really nice guy, probably would have been a great boyfriend, and I didn't end up with the other guy, so maybe I should have taken a chance."

Sophia Vergara and Enrique Iglesias

Sophia Vergara might be one-half of the sexiest couple ever (hi, Joe Manganiello!), but before she bagged her husband and her role as Gloria Delgado-Pritchett on the Emmy-winning ABC mockumentary family sitcomModern Family,she was on the come up, acting in several Colombia telenovelas prior to her big break in the States. During that time, she was dating the King of Latin Pop, Enrique Iglesias.

Kim Kardashian West and Nick Cannon

Right beforeKeeping Up With The Kardashiansaired, throwing Kim Kardashian West into a level of mega fame she still maintains today, the reality star dated Nick Cannon. The two dated for a short time between September 2006 and January 2007.

While Kardashian West hasn't discussed the relationship, Cannon brought it up years later and stirred up some serious drama. During a2012 interview with Howard Stern, he said he broke up with Kardashian West because she didn't tell him she had made a sex tape with Ray J. He explained, "If she might have been honest with me I might have tried to hold her down and be like 'That was before me,' because she is a great girl. She’s actually one of the nicest people you’ll ever meet. But the fact that she lied and told me that there was no tape?"

Cannon added that Kardashian West is a "great businesswoman," saying, "And I still think she might have even had a part to play with (its release)." Yikes.

Drew Barrymore and David Arquette

The jury is still out on whether these two actually dated or not: David Arquette says they did, although he said that Drew Barrymore has denied the claim. Arquette toldPeopleTVthatthe two dated brieflyyears before they played brother and sister inNever Been Kissed. He said, "We also dated, but she denied it on Howard Stern. But, we dated, Drew!" He added, "Sorry, I got a big mouth. I talk. I say it like it is."

Diane Lane and Jon Bon Jovi

Back in the early '80s, before Diane Lane's acting career really took off and before Jon Bon Jovi married his high school sweetheart Dorothea Hurly Bongiovi,Lane and Bon Jovi dated. Lane confirmed the brief relationship on an episode ofWatch What Happens Live with Andy Cohen, saying, "Five months, I was 20. And I think every girl should have such a wonderful experience when she's that young."

In the bookSex, Drugs and Bon Jovi, former tour manager Rich Bozzett also discussed the relationship and explained why Bon Jovi dumped Lane: "The very thing that made Jon feel so passionate about Diane Lane in the first place ended up being the reason for their sudden, unceremonious breakup. Diane was young and wild and loved to party. But she loved to party so much that Jon caught her partying with Richie Sambora. That wasn’t a good day for Jon’s relationship with Diane, to say nothing of Jon-Richie relations."

Kim Kardashian West and Nick Lachey

Okay, Kim Kardashian West and Nick Lachey didn't seriously date. In fact, they may have only been on one date together. The two hung out a bit before Kardashian West was really famous, and Lachey once insinuated that she kind of used him for fame byalerting the paparazzithat they were on a date. He toldDetailsmagazine, "Let's just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside."

Jennifer Aniston and Tate Donovan

Jennifer Aniston and Tate Donovan dated just as Aniston was starting to hit big levels of fame due to her role inFriends. The two met in 1995 through mutual friends. At the time, Aniston toldPeople, "He’s so real, so honest, so funny, so kind and considerate. He’s all these things meshed into one perfect guy."

They dated for a few years, and in 1997, Donovan told People, "I definitely want to get married; she definitely wants to get married. There are no proposals or anything, not yet, but we definitely think about it." However, right before Donovan had a guest role onFriendsas Rachel's love interest (awkward), the two broke up.

Brad Pitt and Thandie Newton

Brad Pitt and Thandie Newton dated in 1994 for about a year after meeting on the set ofInterview with the Vampireback before he was, well, Brad Pitt. They haven't ever really discussed their brief relationship, so there's not much to tell.

Ryan Reynolds and Kristen Johnson

Before Ryan Reynolds became the superstar actor he is today, he dated Kristen Johnson. The two were together for a bit in 1999 and attended the premiere of the film,The Green Mile,together. In a 2020 interview with Andy Cohen forWatch What Happens Live,Johnson was askedabout their relationshipand said, "It was so long ago I forgot, but literally, so nice, great guy, lovely. Lovely person."

Mila Kunis and Macaulay Culkin

Mila Kunis and Macaulay Culkin started dating in 2002 before she became super famous and after Culkin's childhood fame had died down a bit. They dated for eight years before splitting, and a breakup that Kunis described as "horrible," adding, "I f-d up."

During an appearanceon Dax Shephard's podcastArmchair Expert, Kunis said, "I was an a—— in my 20s and I’ll be the first to admit it," she added, "And it’s f—— up what I did. It’s f—— up what I did and it’s f—— up how I did it. When I got to be single I said, ‘I just need to figure myself out.’ I genuinely need to know why I did what I did, and, like, regroup myself as a human being."

We don't know why their relationship ended, but in another podcast,WTF With Marc Maron,Kunis made it clearthat they never recovered from whatever she did, saying, "[We’re] probably not as friendly as we could be, no. There are too many aspects of it that just prevented us from ever moving forward [from the] past. We dated from when I was, like, 18, 19 until 25ish."

John Krasinski and Rashida Jones

John Krasinski and Rashida Jones worked together onThe Office,and their characters dated for a bit. They actually dated in real life, too, before Jones was cast on the show. They haven't talked about it much, but apparently working together afterending things wasn't weird. Jones toldOK!, "It’s not very often you can work with an ex-boyfriend so easily. He’s fantastic; really skillful, honest and direct."

Sandra Bullock and Tate Donovan

Before he dated Aniston, Tate Donovan dated Sandra Bullock for a few years. The two met in 1990 when they worked together on a film calledLove Potion No. 9, and broke up in 1994.

In an interview withVanity Fairin 1995, Bullock said, "I adored Tate so much. It’s like they say, there’s one person in your life, and Tate and I are closer than any two people I’ve ever experienced in my life. There’s nobody that means more to me, and I know for a fact that I mean the most to him, in that certain way. I can’t explain why things worked out the way they did. We both know why it happened."

Katy Perry and Travie McCoy

Right before she became one of the biggest popstars out there, Katy Perry dated Gym Class Heroes frontman Travie McCoy. In 2006, she appeared as his love interest in the music video for "Cupid's Chokehold." The two dated for two years before breaking up in December 2008. McCoy has said thattheir relationship sufferedbecause of his drug use. He said, "She wasn’t stupid...She knew when I was f--d up. I chose drugs over our relationship...As things started taking off for her the more I started to doubt my role in her life. There were times I felt like a stepping ladder."

McCoy said that Perry broke up with him over email, saying, "It started off with, ‘I love you so much I hate to do this...' Someone that you are ready to spend the rest of your life with sends you a f--ing email just s---ing on your whole parade. It destroyed me."

Christian Bale and Drew Barrymore

Christian Bale and Drew Barrymore didn't actually have a relationship, but they did go on a date together before Barrymore basically ghosted him. In 2012, Bale revealed toGQ Australiathat theyhad gone on a dateand then Barrymore never called him back, saying, "We went to see some bloody awful horror film, and that was the end of it. She never called again."

Years later, during an appearance onWatch What Happens Live, Barrymore was askedwhy she had ditched Bale. "I don't know," she admitted. "He was so nice." She added that at that age, she hadn't been trying to date anyone because she was preoccupied with other things.