Everyone knows about high-profile celebrity couples like Jennifer Aniston and Brad Pitt or Ryan Reynolds and Blake Lively, but did you know that before Brad and Jen were a thing that she had a two-year relationship with actor Tate Donovan? Or that prior to marrying Blake, Ryan dated Oscar winner Sandra Bullock.

(via @team_niley_forever)

Believe it or not, there are likely dozens of celebrity couples you totally forgot dated, so we’re here to refresh your memory. Keep scrolling for more of these oft forgotten duos!

1. Adam Brody and Rachel Bilson

Adam Brody and Rachel Bilson

(via @remembertheoc)

The cute costars started dating during the first season of their hit show, The O.C., but called it quits in 2006. Brody is now married to Gossip Girl alum Leighton Meester, while his ex welcomed a daughter with actor Hayden Christensen in October 2014.

2. Ryan Reynolds and Alanis Morissette

(via @90s80s70s60s50s)

The Canadian couple reportedly met at Drew Barrymore’s birthday party in 2002 and got engaged in June 2004. In 2005, the Deadpool star told People: “I love her music … It can be awkward when she walks in and I’m listening to it in my underwear dancing.” They called it quits in 2006.

3. Tom Cruise and Cher

(via @urgonnadiealone)

The superstars met at Sean Penn and Madonna’s wedding in 1985 and dated briefly thereafter despite a 16 year age difference. “It was pretty hot and heavy for a little minute,” Cher revealed on Watch What Happens Live With Andy Cohen in 2013.

4. Emma Stone and Kieran Culkin

(via @_emma_jean_stone_)

The La La Land actress and the Succession star were rumored to be an item around 2009 and 2010 after meeting on the set of the movie Paper Man. They were able to keep their relationship a secret in part because neither of them were super famous at the time, but broke up after about two years together. Stone went on to date Andrew Garfield, while Culkin married a woman named Jazz Charton in 2013.

5. Kate Hudson and Alex Rodriguez

(via @katehudson)

The Fabletics creator and the former Yankee dated after her divorce from Chris Robinson in 2009, but jealousy over one of the athlete’s famous exes reportedly ruined their relationship. “Kate was mad with jealousy,” a source said of the pair in January 2010. “She gave A-Rod three chances to stop contacting Madonna.”

6. Tyra Banks and Drake

Tyra Banks and Drake

(via @litglasspromotions)

“It was just one date,” the Grammy winner told Ellen DeGeneres in September 2013. “We went to Disneyland in disguise actually, which was really fun. I don’t even know if it was like a date. It was like a get-together. We’re still really close.”

7. Janet Jackson and Matthew McConaughey

(via @stylingitvintage)

After meeting at the 2002 Grammy Awards, the duo dated for a short period of time. “I guess we did [date]. He is such a great guy and a sweetheart,” the “All For You” songstress said in 2006. “It was just for a minute, that’s why I’m so hesitant to mention it.”

8. Justin Timberlake and Jenna Dewan

(via @jennadewan)

Prior to kicking off her own career in the entertainment industry, the Step Up star worked as a backup dancer for the “Say Something” crooner. They dated briefly after Timberlake and Britney Spears broke up around 2002. “We were like friends… that dated,” Dewan confirmed in May 2017.

9. Taylor Swift and Taylor Lautner

(via @crsp4)

The Taylors dated for a few months in 2009. The Twilight star was later rumored to be the inspiration for Swift’s song “Back to December,” which she has said “was about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him.”

10. John Krasinski and Rashida Jones

(via @dundermifflinpaperco)

Believe it or not, the twosome were an item before working on The Office together. “He’s one of my closest friends,” Jones said in 2006, according to Screenrant. “He was incredibly supportive of me getting this job, and for the most part, if you go out with somebody and it doesn’t work out, there’s always a reason why you liked the person to begin with.”

11. Matthew Perry and Lizzy Caplan

(via @mattyperry4)

The Friends alum and the Mean Girls star dated for six years before ultimately calling it quits in 2012. They were so secretive about their relationship that most people didn’t even know they were dating until more than a year after they broke up. While Perry is now single, Caplan married actor Tom Riley in 2017.

12. Christina Applegate and Brad Pitt

(via @historyphotographed)

The twosome walked the red carpet together at the MTV Movie Awards in 1989, but things went south when the Dead to Me star left the Oscar winner for another well-known man in the midst of their date that night. Despite Andy Cohen’s best efforts, Applegate remained mum when asked exactly who she ditched Pitt for in August 2015. She did, however, share that she and the Ad Astra star never dated again.

13. Megan Fox and David Gallagher

(via @thatso2000sbitch)

Before Fox starred in blockbusters such as Transformers and Transformers: Revenge of the Fallen, she dated 7th Heaven alum David Gallagher. They were an item from 2003 to 2004, according to E! News, and were spotted on several red carpets together.

14. Busy Philipps and Colin Hanks

(via @BusyPhilipps)

The duo met while attending Loyola Marymount University and dated for a few years. “He was my college boyfriend,” the Cougar Town alum said on Live With Kelly and Ryan in January 2017. “We are very, very close friends now. We dated for a long time.”

15. Jennifer Aniston and Tate Donovan

(via @90ssclassy)

As Friends fans might know, these two appeared on several episodes of the hit show together in 1994. Their on-screen relationship was modeled after their real-life partnership, which lasted for about two years, but they were actually in the midst of a breakup as they were working together on Friends. “That was just tough,” Donovan told Us Weekly in September 2018.

16. Kirsten Dunst and Jake Gyllenhaal

(via @80sradical)

The young actors were an item for almost two years before breaking up in 2004. They were introduced through Gyllenhaal’s sister, actress Maggie Gyllenhaal, who co-starred alongside Dunst in Mona Lisa Smile. The Bring It On star referenced the split years later, explaining: “He’s a stay-at-home boy and I’m an out-on-the-town girl.”

17. Julia Roberts and Matthew Perry

(via @golldies)

This unlikely pair met when the Pretty Woman star guest-appeared on an episode in the second season of Friends in 1996. They went on “a few dates,” according to People, but the “casual” romance quickly fizzled.

18. Winona Ryder and Matt Damon

(via @winonaryderofficial)

The twosome were introduced by Gwyneth Paltrow in 1997, as Paltrow was dating Damon’s best friend, Ben Affleck, at the time. The Stranger Things actress accompanied Damon to the 2000 Golden Globes, but the relationship didn’t last long. “Matt couldn’t be a greater, nicer guy,” Ryder told Blackbook Magazine in 2009. “I’m really lucky that I’m on good terms with him.”

19. Jennifer Garner and Michael Vartan

(via @enews)

The Alias costars dated after Garner’s divorce from Scott Foley in 2003 and were together for about six months. They remain on good terms, and the 13 Going On 30 star even wished her ex a happy birthday with a sweet Instagram post in November 2018. “Can you believe this baby face is 50?! Happy birthday, #MichaelVartan,” she captioned a throwback shot of them in character. “#alwaysanALIASgirl#sydneyandvaughnforever.”

20. Rachel McAdams and Michael Sheen

(via @rachelmcadams1)

These two met while filming Midnight in Paris and dated for a few years before parting ways in 2013. Over the course of their relationship, they made a point never to spend too much time away from one another. “Michael and I never spend more than three weeks apart. We rack up a lot of air miles, but you have to be quite adaptable in this business whether you are in a relationship or not,” the Mean Girls star told Stella magazine in January 2012.

21. Madonna and Sean Penn

(via @Madonnabible)

The eccentric duo got married in 1985, but divorced four years later. Though their marriage didn’t work out, the stars have no ill will toward one another. “Ah, I love my first wife very much,” Penn said during a March 2018 appearance on The Late Show, when he was asked to pick between his former spouse and Britney Spears. “There’s no [comparison]… you don’t compare those things.”

22. John Mayer and Jessica Simpson

(via @justjared)

This duo dated for almost a year in 2006, shortly after her divorce from Nick Lachey. As Simpson explained in her memoir, Open Book, the partnership was turbulent. She claimed that Mayer broke up with her nine times, and each time it was over email. He reportedly even followed up one breakup email by sending her the song “Angel” by Aerosmith. The “Gravity” singer has since apologized for his behavior.

23. Miley Cyrus and Nick Jonas

(via @team_niley_forever)

The former Disney Channel stars dated when they were teens, but only confirmed their relationship long after they broke up. “At first I bawled for a month straight. I was so sad. I just went into this weird funk. And I dyed my hair black,” Cyrus told Seventeen in August 2008. “When we were dating, Nick wanted me to get highlights, and so I did that, and I got myself looking great. And then, on the day we broke up, I was like, I want to make my hair black now. I don’t want to look pretty; I want to look hardcore. I was rebelling against everything Nick wanted me to be. And then I was like, I’ve got to be by myself for now, and just figure out who I really am.”

24. Hilary Duff and Joel Madden

(via @hilaryduff)

The Lizzie McGuire alum was 16 when she started dating Joel in 2004, and they broke up two years later. “It was so all encompassing. It was so intense. It was my life,” Duff said of the relationship in November 2016. “It was like every minute of my day. It was pretty major.”

25. Zachary Quinto and Jonathan Groff

(via @kristenbell_rp)

The Glee alum confirmed he was dating the Mindhunter actor in an interview with Out Magazine in 2012. “I’m incredibly happy, I’m incredibly lucky,” he said of their relationship at the time. “I found myself in a pattern of being attracted to people who were somehow unavailable, and what I realized was that I was protecting myself because I equated the idea of connection and love with trauma and death.” The pair broke up the following year.

26. Jennifer Aniston and John Mayer

(via @jenanistonheart)

The couple debuted their love on the red carpet in Feb. 2009, but broke up shortly after. Mayer hinted in Feb. 2019 that the duo’s age difference was a factor in their split. “I’ll always be sorry that it didn’t last,” he said at the time. “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32.”

27. Cameron Diaz and Justin Timberlake

(via @historic.celebrity.couples)

Believe it or not, his duo met at the 2003 Nickelodeon Kids Choice Awards and dated for four years. “It has always been our preference not to comment on the status of our relationship, but, out of respect for the time we’ve spent together, we feel compelled to do so now, in light of recent speculation and the number of inaccurate stories that are being reported by the media,” Diaz and Timberlake said upon ending their relationship in 2007. “We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another.”

28. January Jones and Ashton Kutcher

(via @lazyromance)

The Mad Men alum revealed in a 2009 interview with GQ that Kutcher was her first boyfriend. “[He] was not supportive of my acting,” she told the publication at the time. “He was like, I don’t think you’re going to be good at this … He only has nice things to say now. If anything, I should thank him, because the minute you tell me I can’t do something, that’s when I’m most motivated.”

29. Sandra Bullock and Ryan Gosling

(via @ryangoslinguk)

This pair dated in 2002 and 2003, when she was 38 and he 22. They walked the red carpet together at the Cannes premiere of their film Murder by Numbers and the premiere of Gosling’s flick, The Believer.

30. Rihanna and Shia LaBeouf

(via @everihthang)

The “Diamonds” songstress is typically coy about her dating life, but she spoke about her lone 2007 date with the Even Stevens alum two years after the fact, implying she texted him and they went to dinner: “I was filming a sword fight when I got the message. I said, ‘Can this be my life?’ It never got beyond one date. The spark wasn’t there,” she said at the time. “We weren’t passionate about each other in that way, so we remain friends.”

Speaking of couples you may have forgotten, THESE are some of the most eyebrow-raising celebrity pairs of 2019!

30 Celebrity Couples You Forgot Dated