They Dated?! Surprising Celebrity Hookups

In an interview with Vulture, the pop diva confirmed that two of her 1998 tracks -- "My All" and "The Roof" -- were about the former New York Yankees shortstop. Carey and Jeter's fling came toward the end of her marriage to Tommy Mottola, with whom she finalized her divorce in 1998.

The musician and former pro athlete met at a dinner party and began flirting via text message shortly thereafter. As Carey reveals in her upcoming memoir, The Meaning of Mariah Carey, the fact that many fan theories about her songs were "already out there" made it easier for her to share further details publicly. As such, Carey told Vulture that she "of course" remembers every detail about her first kiss with Jeter, which she describes in detail on the track "The Roof." The kiss itself took place on Jeter's roof with Carey sporting aa leather Chanel skirt and a bottle of Moët sitting nearby.

On an October 2019 episode of the podcast Armchair Expert With Dax Shepard, the Parenthood star chatted about his whirlwind relationship with Hudson back in 2007. While on the ep with her brother, Oliver Hudson, the two fondly spoke about their few months together. Shepard and Hudson first met at a backyard party at Tobey Maguire's, but both were in relationships at the time (Hudson was still married to The Black Crowes' Chris Robinson, while Shepard was dating Briegh Morrison). About a year later, the newly single actors were both at Nobu when they decided to mess with the paparazzi, and they admitted that their relationship started off as a friendly joke that turned romantic.

"First of all: very, very fun. [A] very memorable, very wonderful, fun experience,” Shepard said of their relationship, to which Hudson added that their time together was "a blast" and that their personalities were "super compatible." While it was Shepard's first monogamous relationship in 15 years, he ultimately felt "less than" around Hudson, who was already well-known for her breakout role, Almost Famous, and they parted ways, with the actress saying their breakup was "mutual-esque." Shepard is now famously married to Kristen Bell, with whom he shares two children, and Hudson welcomed a daughter with her boyfriend of three years, Danny Fujikawa, in 2018; she also has two sons from previous relationships. 

The actress dated the 7th Heaven star from 2003-2004 before moving on to Brian Austin Green.

Fox and Green wed in 2010 and share three sons, Noah, Bodhi and Journey. The Transformers actress initially filed for divorce in 2015 but they later reconciled before splitting up again in 2020. Fox has since moved on with rapper Machine Gun Kelly.

When the Dancing With the Stars judge sat down with the ladies of The Talk in October 2018, she revealed that she'd once had a romantic fling with the Full House star in the early 1990s, when she was a dancer on In Living Color. "We did date," she shared. "When I was a Fly Girl, the dreamiest thing happened. Somebody was like, 'Somebody wants to meet you across the room.' The room parted and on the other side of the room was John Stamos."

The pair dated for "a little while" but she said they ultimately split because, "I was not quite ready for somebody as good as John Stamos in my life at that moment." Despite a failed attempt at reconciling, the two never reconnected romantically. However, when their paths crossed on DWTS years later, Inaba says Stamos graciously came up to her to congratulate her on her career. "He came right up to me and said, 'I'm so happy for your success. I wish you all the best. It's great to see you.' And I was like, 'Oh my God," Inaba recalled, later describing the actor as "the loveliest human being in the whole world."

While on Watch What Happens Live With Andy Cohen in May 2017, the Real Housewives of New York City star responded to rumors that she had a fling with the former MLB pro in 2009, after his divorce.

When asked point-blank if she ever dated A-Rod, Frankel answered, "What is 'used to date' mean? I went out with him on two dates." As for whether they kissed, she admitted, "I honestly don't remember." Rodriguez has since become engaged to Jennifer Lopez.

On Watch What Happens Live With Andy Cohen in May 2017, the World of Dance hosted admitted that she and Timberlake "dated, not that long.

Tatum said the relationship occurred when she was JT's backup dancer after his split from Britney Spears, explaining, "We were like friends ...that dated."

The Teen Wolf star revealed to Seventeen that Cyrus was his first kiss. "I worked on a TV show called Doc, starring Billy Ray Cyrus, when I was nine-years-old. His daughter, Miley Cyrus, was my first kiss and girlfriend," Posey told the mag. "We dated for two years and broke up when we were 11. I saw her three years later on TV, and freaked out! We're still friends."

Cyrus has dated quite a few famous faces since, but her best-known relationship was with Liam Hemsworth, with whom she was with on-and-off for nearly a decade before they divorced in 2019 after less than a year of marriage. The Happy Hippie has since moved on with Australian musician Cody Simpson. As for Posey, he was engaged to his childhood sweetheart, Seana Gorlick, but they broke up in 2013 after dating for 10 years.

The actors had quite the amicable breakup after dating when they were both students at Loyola Marymount University. "We met when I was 18 and Colin was 19," Philipps recalled while co-hosting Live! With Kelly.

"We are very, very close friends now. His wife [Samantha Bryant] and I are tight, he and my husband [Marc Silverstein] hang out. We go on vacation together... And we hang out a lot. And I do have moments where I think, ‘How cool that we knew each other at this formative moment together?’”

Gwyneth Paltrow introduced these two in 1997, which isn't nearly as random as it sounds -- the actress was dating Damon's BFF, Ben Affleck, at the time. The two hit it off and started dating, though reports are conflicting as to whether it was before or after Damon broke up with his Good Will Hunting co-star, Minnie Driver.

The pretty pair made their first red carpet appearance at Harvey Weinstein's pre-Oscar party in March 1998, but they were done by 2000, shortly after they walked the red carpet at the Golden Globe Awards in January.

During an episode of RuPaul's podcast, What's the Tee?, the Parks and Recreation alum revealed that she dated her Scott Pilgrim vs. the World co-star for a year and a half.

"We drove across the country after we shot that movie and almost got married in Vegas," she shared, noting that she found Cera "sexy." Plaza added, "He's just a weird little freak and we speak the same language. He's one of the funniest people I know."

The music icon reportedly dated the actor in 2002, with the two hitting it off after meeting at the GRAMMYs. Despite McConaughey saying at the time that the two were "just friends" at the time, Jackson later admitted to the brief fling before getting serious with producer Jermaine Dupri.

The Texas-born actor now has three children with wife of eight years Camila Alves, while Jackson has since split from Wissam Al Mana, whom she married in 2012 and shares one son.

Despite their 16-year age difference, these two were a secret item in the '80s. Cher 'fessed up to the surprise relationship on Good Morning America in 2008, and she had nothing but good things to say about Tom.

"He's just the most adorable man you can imagine," she gushed.

This was a summer fling no one saw coming!  The Baywatch star was spotted packing on the PDA in Sardinia, Italy, with the Fast & Furious actress, nearly 10 years his senior.

The two were seen flying into Sardinia Airport in a private jet on July 4th, 2014, and were later caught cuddling and kissing on a boat together. Not too long after pics of their romance surfaced, the relationship reportedly fizzled. 

The Lost in Translation director Sofia Coppola dated Reeves in 1992.

This was after her father, the legendary Francis Ford Coppola, directed the actor in Bram Stoker's Dracula. 

Though she's better known for dating her late Glee co-star, Cory Monteith, it turns out she was previously linked to another star of the hit Fox show. In her book Brunette Ambition, Michele revealed that she actually dated Morrison before the two landed their roles on Glee.

"Matt had been a friend of mine for years, and in fact we'd actually dated back in the day for a Broadway beat," she wrote (via Us Weekly).

The pair dated for two years from 2006-2008. But there's no controversy here -- Goodwin's pal told People that the split was "amicable" and that the two just "wanted different things."

The actress wed her Once Upon a Time co-star, Josh Dallas, in 2014, while Klein -- who famously dated Katie Holmes before she began dating Tom Cruise -- has been married to Laina Rose Thyfault since 2015.

Turns out Groban is quite the ladies’ man!

Besides being linked to January Jones and reportedly Katy Perry, the opera singer also dated Trachtenberg in 2012.

The actors reportedly had a brief fling in 2009. They were spotted kissing at HBO's Emmy party and later left the soiree side by side, E! reported.

That same year, the How I Met Your Mother star also briefly dated Michelle Trachtenberg, according to Us Weekly, but nothing serious came out of the pairing.

The Pride and Glory co-stars were once a thing! Bell talked about their brief 2006 relationship to GQ, revealing that the two are still on good terms.

"He’s such a friggin' awesome dude, and I'm friends with all of my exes. I'm not a hater," she told the magazine.

Aside from famously romancing Mandy Moore and Lindsay Lohan and formerly being in a longterm relationship with Demi Lovato, Valderrama also reportedly hooked up with Avril Lavigne in 2009. People reported that onlookers spotted the two looking "super cozy" at Los Angeles hotspot Wonderland.

"There were others at the table but you could tell they only had eyes for each other," the source said.

The Full House star reportedly dated Moore in the early '80s, when the two starred in General Hospital together.

He was also linked to Paula Abdul in the '90s.

The "Fergalicious" singer dated Timberlake in the late '90s but later admitted that she was embarrassed by their nearly six-year age gap. (Fergie was born in March 1975, while Timberlake was born in January 1981.)

Things seem to have ended amicably, however, as the "Sexy Back" singer collaborated with the Black Eyed Peas on "Where Is the Love?" in 2003. Fergie later married Josh Duhamel in 2009. They had one son together, Axl, but split in 2017, while Timberlake has been married to Jessica Biel since 2012, and they share one son, Silas.

The duo was said to have briefly dated in 2000 but romance rumors came roaring back in 2005 when they were reportedly caught making out in the back of a limousine in New York City.

Clooney is now happily married to Amal Clooney, with whom he shares twins, while Liu had a son in 2015. 

Ready for this?

It was a true case of opposites attract -- or perhaps just a hunger for publicity -- that drove the reality star and the Smashing Pumpkins frontman to walk the red carpet together at Bravo's 2nd Annual A-List Awards in 2009.

Before his three-year relationship to Olivia Munn, according to Us Weekly, the Green Bay Packers quarterback dated Szohr in 2011, before briefly reuniting around Rodgers' birthday in 2017.

Rodgers is now engaged to actress Shailene Woodley.

Whoa! The Blossom alum and the actress dated back in 1994, before Russell hit it big with Felicity.

These days, Lawrence has two daughters with his second wife, Chandie Yawn-Nelson, while Russell was married to carpenter Shane Deary, with whom she has a son and a daughter, and is now with her The Americans co-star, Matthew Rhys.

Besides being linked to Keira Knightley, Lindsay Lohan and Sienna Miller, Mr. Fifty Shades of Grey also reportedly dated Moss after the two starred in a super-sultry Calvin Klein campaign together.

Dornan has since settled down with wife Amelia Warner.

The man known as Captain America reportedly dated the Shameless star in 2007, and they weren't shy about it! According to E! News, the two were spotted at the Hollywood Roosevelt Hotel by an onlooker, who reported that the two photogenic stars were "making out in front of everyone."

Evans had previously been in a five-year relationship with Jessica Biel that ended in 2006, and the pair had appeared in two films together, Cellular and London.

Though dating rumors swirled around rapper The Game and Khloe Kardashian, he recently admitted that it's actually her sister that he had previously dated. "I went and dated Kim for a while. A little, short while. Me and Khloe are cool," he told BBC Radio's DJ Charlie Sloth about all the then-buzz.

He added that he doesn't "remember that timeline" of exactly when he dated the reality star but noted that it was "a long time ago." Kardashian West is now famously married to Kanye West, and the pair have four children together.

Shields dated Neeson in 1991 for about a year, but the Taken star was apparently so smitten with the Blue Lagoon actress, that he "considered marrying her." This was far from Neeson's first foray with dating a famous actress. Four years earlier, Neeson embarked on a short-lived romance with his Satisfaction co-star Julia Roberts when she was 19 and he was 35.

The pair even moved in together in Venice, California, before calling it quits the next year, according to People. He also had a four-year relationship with Helen Mirren that began in 1981, after the two met on the set of Excalibur.

Costner reportedly dated the supermodel in 1996, with the two even shacking up together.

Their relationship lasted less than a year.

According to People, Mendes briefly stepped out with the former SNL cast member in 2011, before settling down with current husband Ryan Gosling.

Sudeikis also found love after dating the Place Beyond the Pines beauty -- he married actress Olivia Wilde and they have two kids together. The couple split in 2020.

Not only has he dated Taylor Swift, Katy Perry, Michelle Branch and Jessica Simpson (not to mention Jennifer Aniston!), there was another songstress whom he went "a thousand miles" with.

The Connecticut native dated Carlton on-and-off for about a year in 2002.

The fashion designer and the Thirty Seconds to Mars frontman were briefly an item in 2005. Olsen and Leto reportedly rekindled their romance in 2012, when they had dinner at the Polo Lounge in Beverly Hills, California. According to the New York Daily News, the two "couldn't stop touching each other."

Though they didn't end up together, things seem to be amicable between them, as they posed together with Olsen's twin sister, Mary-Kate Olsen, at the 2018 Met Gala.

The Friends star reportedly hooked up with the Hangover actress in 2003 but the fling didn't last long.

They were already over by the end of that year.

These two confirmed their romance in 2007 when they attended the opening night of King Lear in New York City.

The low-key couple reportedly dated for a year before calling it quits. These days, Perabo has been married to Stephen Kay sine 2014, while Rockwell is dating actress Leslie Bibb.

Griffin opened up to ET in 2009 about her surprising, short-lived romance with the director in 1995. "I did also date Quentin Tarantino although I did not sleep with him and I did not have sex with him because he wanted to cuddle. [...] And I am telling you openly, and with shame, that I did not close the deal with Quentin Tarantino," she told ET.

"And let's go with because he was so in love with me that he knew if we had sex once he would fall too deeply in love with me."

The Sex and the City star reportedly dated Willis in 2003 after meeting at a party thrown by Diddy.

The two never quite got serious.

Besides having been linked to Emilia Clarke, Audrina Patridge and Amanda Bynes, the Family Guy creator also dated the Bring It On star in 2008.

These days, MacFarlane remains a bachelor, while Dushku married Peter Palandjian in 2018.

The most random pair ever?! Hilton and Kilmer shocked plenty of people in 2006 when pictures of the two making out hit the Internet.

The pics were reportedly from 2002 when Kilmer was filming Wonderland, in which Hilton had a cameo.

Looks like the chemistry between Silverstone and Dorff in Aerosmith's memorably steamy Cryin' music video wasn't just for the cameras.

The actor admitted to HuffPost Live years later that the 1993 music video actually led to a "little romance" between him and Silverstone.

Hewitt appeared on The Wendy Williams Show in 2010, where she revealed that her first date was with none other than The Wonder Years star! "We went to a comedy club and we went to dinner and he dropped me off at home," the 9-1-1 star dished about the memorable experience, which happened when she was 14 and Savage was 16.

But in the end, the night turned out to be a bust. "He never called me again," she said. Hewitt seems to be doing OK, however -- she wed Brian Halliday in 2013.

Cruz and Harnett made a beautiful pair when they briefly dated in 2007.

These days, Hartnett has two children with his wife, British actress Tamsin Egerton, while Cruz has been married to Javier Bardem since 2010.

Before she married Chris Hemsworth, the Fast & Furious 6 actress was in a relationship with Brody.

They began dating around 2008, and they were so serious that the Oscar winner bought Pataky a castle in upstate New York for her birthday (he shared the story with Hello! Magazine Canada).

Hough had a childhood romance with her one-time Dancing with the Stars co-star. "It didn't bother me because it was Mark," Julianne's brother, Derek Hough, told People.

"So, I guess no girls are really off-limits!" Ballas wed singer-songwriter BC Jean in 2016, and the two perform together as the duo Alexander Jean, while Hough split from husband Brooks Laich in 2020 after three years of marriage.

Besides dating heartthrobs Zac Efron and Taylor Lautner, Collins was also linked to Overstreet in 2012. But their relationship didn't last long, as the actress moved on to her Mortal Instruments: City of Bones co-star, Jamie Campbell Bower.

That didn't last either, though, but she has been Instagram official with boyfriend Charlie McDowell in 2019.

According to MSN, Sheen dated Ryder in 1986, when the two met on the set of Lucas. The actor even claims to have given Ryder -- born Winona Horowitz -- her stage name. "We were listening to the Doors, to 'Riders on the Storm.' [Winona's] real name is Horowitz," he said during an appearance on CenterStage.

"And I said, 'You know, I'm thinking Winona Ryder sounds cool,' and she was like, 'Yeah!'"

Ford briefly dated Driver -- 28 years his junior -- in 2001.

These days, Ford is married to Ally McBeal star Calista Flockhart, while Driver is single but has previously also dated Matt Damon and John Cusack.

Who knew that Depp dated the Dirty Dancing star, let alone that they were engaged?!

The two were set to walk down the aisle in 1990, though it didn't happen, and Grey has also been linked to Matthew Broderick and Good Morning America anchor George Stephanopoulos.

These two had a brief fling in 2003. According to People, Alba and Wahlberg were spotted getting cozy in Miami Beach on New Year's Eve and briefly dated thereafter.

By January 2005, Alba met her future husband Cash Warren, who was an assistant director on her film Fantastic Four. As for Wahlberg, he has been married to Rhea Durham since 2009.

The Weeds co-stars' on-again, off-again relationship ended when they broke off their engagement in 2008.

Morgan has since moved on with former One Tree Hill actress and MTV VJ Hilarie Burton, whom he married in October 2019 and shares a son, Augustus, and a daughter, George, with. 

Osbourne revealed a surprising fling with the former late-night host during an episode of her show, The Talk. "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," she recalled.

"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..."

According to MSN, Danes and Damon -- eight years her senior -- briefly dated while shooting their 1997 film The Rainmaker.

These days, the two are happily married with children -- Danes to fellow actor Hugh Dancy and Damon to Luciana Barroso, a former Miami Beach bartender.

The Twilight and Revolution star once dated the Scream queen! The two even starred in a movie together, 2003's Lost Junction.

Coincidentally, Burke was also a guest star on Campbell's hit show Party of Five in 1994, though the two didn't meet until 2002.

A case of puppy love!

According to Buzzfeed, the two dated from 1981-1982, when Wright was just 15 and Sheen was 16.

The actors have known each other since before they were famous.

They still had Twilight and Gossip Girl fans in a tizzy when they were spotted making out on the way to LAX after the 2009 Teen Choice Awards.

The singer-songwriter and the Good Wife star dated in 2003, and the two even went public together when Charles accompanied Crow to the GRAMMYs that year.

The award-winning singer reportedly broke up with him just two months later because she sensed that he wasn't "The One." Before Crow, the actor dated Jennifer Connelly for three years until 1999.

Simpson 'fessed up to dating the Supernatural star in 1998 when she was just 18, and things didn't end on a good note between the two Texans. The "Angels" singer called out Ackles in an episode of her reality show, Newlyweds, for allegedly cheating on her with LeAnn Rimes. 

These days, the two have both found love with other people -- Simpson shares three children with her husband, former NFL player Eric Johnson, while Ackles also has three children with his wife, One Tree Hill actress Danneel Harris.

The man known as James Bond dated the supermodel in 2004, but the British couple lasted less than a year.

Craig would go on to tie the knot with actress Rachel Weisz in 2011, while Moss was married to Jamie Hince from 2001-2006.

Barrymore was busted in a steamy liplock with Gossip Girl's resident bad boy at a Kings of Leon concert in 2008. But their May-December romance (she was 33 at the time, he was 21) turned out to be more of a fling than a long-term relationship. The two never went public, and Barrymore later married art consultant Will Kopelman, with whom she shares two daughters and divorced after four years of marriage in 2016.

Westwick wasn't Barrymore's first surprising relationship, however -- back in 1989, she dated Corey Feldman at the height of his fame, but the relationship quickly fizzled when the actress reportedly broke up with her beau.

Goldblum reportedly dated, the Sex and the City star -- 12 years his junior -- in 2002.

The pair later broke-up quietly. 

The She's All That star dated the Boy Meets World fan-favorite back in 1999, though the two kept their relationship pretty private.

Moving forward a few years, Cook was married to Vampire Diaries star Daniel Gillies, while Strong wed actress Alexandra Barretto in 2013.

The A-listers dated in 1995, and their relationship reportedly didn't last long.

These days, Roberts is married to cameraman Daniel Moder, while Day-Lewis is married to Rebecca Miller -- playwright Arthur Miller's daughter -- with whom he has two sons with.

The journalist revealed she went on a date with the Full House star during an interview with Howard Stern, but unfortunately, the sparks didn't fly, though Couric did say that Saget  "was really fun."

"I had fun [but] I don't think I did it for him," she explained. As for the comedian never calling her again, Couric was hardly heartbroken, assuring Stern that it was "alright."

The two were briefly linked in 2007, when People reported that they were engaged in a "full-on PDA display" at their reserved table at a Xenii after-hours party in Los Angeles.

Diaz is now married to Good Charlotte musician Benji Madden, and they welcomed a daughter in late 2019, while Gibson wed his second wife, Samantha Lee, in 2017.

The two reportedly dated for six months in 2004 after meeting on the set of Brick.

These days, Good is married to Columbia Pictures Vice President and preacher DeVon Franklin, while Gordon-Levitt married entrepreneur Tasha McCauley in 2014, and they have two sons together.

The Mad Men alum dated the funnyman, 16 years her senior, in 2002.

The romance reportedly went sour when Carrey found out that Jones was also seeing socialite Brandon Davis, who himself famously dated Mischa Barton at the height of her O.C. fame.

 

Pink revealed that she one had a secret relationship with the *NSYNC member when she opened up for the boy band in the early 2000s.

"Joey Fatone was in love with me," she told Glamour magazine. "He took me to Friendly's on a date and he bought me an ice cream. Such a sweetheart. He asked my dad's permission!"

The actress dated the NFL quarterback in 2002 after reportedly requesting her agent to set her up with Brady -- but their relationship fizzled after only a month.

Brady married supermodel Gisele Bündchen in 2009, and the pair have two children together, and he also has a son from a previous relationship to actress Bridget Moynahan.

The Spice Girl dated O'Connell in 2004. 

It didn't last long -- the two broke-up that same year.

 

The 21 Jump Street star Dave Franco dated Glee's Dianna Agron for about a year in 2008. 

They later split. Franco is married to GLOW star Alison Brie.