18 Old-School Celebrity Romances You Definitely Forgot About

Very few Hollywood relationships stand the test of time. No matter how hard we all root for our favorite celeb romances (looking at you, John Legend and Chrissy Teigen), some love stories just aren’t meant to be. With new relationships starting and ending every day it can be hard to keep track of which of your favorite celeb couples actually dated (and how long ago it actually happened!).

Do you remember who Kim Kardashian dated before she was married to Kanye West? Or which co-stars from The Office dated before starring opposite each other on screen? The truth may surprise you! While these celeb romances may not have lasted very long, it sure is entertaining to see which Hollywood stars pursued each other back in the day. Keep on reading to see 18 celebrity couples you may have forgotten about!

18. Justin Timberlake and Jenna Dewan

On a 2017 episode of Watch What Happens Live with Andy Cohen, Jenna Dewan revealed that she briefly dated Justin Timberlake after his breakup with Britney Spears in 2002. She said, “We dated, not that long. We were like friends… that dated.” After their short romance, Justin ultimately married Jessica Biel in 2012, and they welcomed a son in 2015. Jenna married Channing Tatum in 2009, and together they have one daughter – though the couple announced their separation in April 2018.

17. Alexis Bledel and Milo Ventimiglia

Alexis Bledel and Milo Ventimiglia starred as a couple on-screen in Gilmore Girls as Rory Gilmore and the bad boy-turned-boyfriend Jess, and the two eventually moved their relationship off-screen, too. They dated for three and a half years from 2002-2006. Alexis went on to marry Vincent Kartheiser in 2014, and they had a child together in 2015. While Milo briefly dated his Heroes co-star Hayden Panettiere from 2007-2009, his love life has been kept under the radar ever since.

16. Kate Hudson and Alex Rodriguez

Rom-com queen Kate Hudson has seen her fair share of romances on and off the screen, but do you remember when she dated baseball star Alex Rodriguez? The two dated for seven months in 2009 but broke off the short fling in December of that year. Now, Alex is dating Jennifer Lopez, and Kate has two kids with her former husband Matt Bellamy and is expecting a third child with her current boyfriend Danny Fujikawa

15. Jared Leto and Cameron Diaz

In 1999, Jared Leto and Cameron Diaz kicked off a four-year relationship, and while it was never confirmed, Diaz sparked rumors that the two were engaged when she wore a ring that looked a lot like an engagement ring to the 2003 Golden Globe Awards. Ultimately, the two broke it off in 2003, and Cameron went on to date Justin Timberlake and Alex Rodriguez before marrying musician Benji Madden in a surprise ceremony in 2015.

14. Alanis Morissette and Ryan Reynolds

It was at a 2002 birthday party for Drew Barrymore where Canadian singer Alanis Morissette met Canadian actor Ryan Reynolds. The two hit it off, and they began dating shortly after. By 2004 they were engaged, but in 2007 they announced their official separation before they set a wedding date. Alanis then confirmed that her album Flavors of Entanglement was written the result of her grief for their breakup, and the song “Torch” is specifically about Ryan. Now, Alanis is married to rapper Mario “Souleye” Treadway, and they have two children. Ryan has since married and divorced Scarlett Johansson, and he is now married to Blake Lively, and they have two daughters together.

13. Julia Roberts and Liam Neeson

Though Julia Roberts was just 19 when she met 35-year old Liam Neeson on the set of the drama/romance film Satisfaction in 1988, sparks flew and the two began seeing each other. Julia moved in with Liam in his California home, and the two dated until 1990. Now, Julia is currently married to cameraman Daniel Moder, and they have three children together. Liam married actress Natasha Richardson in 1994, and they had two children together – but Natasha tragically died in 2009 as a result of head injuries during a skiing accident.

12. Penélope Cruz and Tom Cruise

After appearing together in the 2001 thriller film Vanilla Sky, Penélope Cruz and Tom Cruise began dating for three years, but broke off their relationship in 2004. Penélope went on to marry her former co-star Javier Bardem in 2010, and they went on to have two children together. Tom married Katie Holmes in 2006 – they had one daughter together, though they ultimately split in 2012, with many speculating that Tom’s involvement in the Church of Scientology was a factor in the separation.

11. Mila Kunis and Macaulay Culkin

Back in 2002, Mila Kunis began dating Macaulay Culkin – they kicked off an eight-year relationship that they both kept fiercely private. While rumors swirled that the two planned on getting married, they both denied the claims, with Mila saying that marriage wasn’t something that was important to her. Ultimately, Mila’s publicist confirmed their split in 2011, saying, “The split was amicable, and they remain close friends.” Macaulay has since been linked to actresses Jordan Price and Brenda Song, while Mila married her That ‘70s Show co-star Ashton Kutcher in 2015. Since then, the couple has had two children together.

10. John Krasinski and Rashida Jones

Before they starred as a couple (and then an ex-couple) on The Office, John Krasinski and Rashida Jones dated in real life, too. While it didn’t work out for Jim Halpert and Karen Filippelli, John and Rashida only dated for a year from 2005-2006, too. Rashida spoke to OK! about working with her ex-boyfriend in 2008, saying, “It’s not very often you can work with an ex-boyfriend so easily. He’s fantastic; really skillful, honest and direct.” While Rashida’s dating life has been kept on the down low, John ultimately married actress Emily Blunt in 2010, and they have two daughters together.

9. Katy Perry and Travie McCoy

Before her musical breakthrough with her second album One of the Boys (featuring songs like “I Kissed a Girl” and “Hot n Cold”) Katy Perry starred as the love interest for her then-boyfriend Travie McCoy’s music video for the song “Cupid’s Chokehold.” Katy and Travie, who is the lead singer of Gym Class Heroes, dated for two years from 2006-2008. Though Travie said they had no bad blood, he’s rumored to be the center of Katy’s song “Circle the Drain,” which talks bluntly about a former flame’s drug addiction and all the stress it put on a relationship.

8. Madonna and Sean Penn

Both Madonna and Sean Penn have had tumultuous romantic lives that have been scrutinized by the press and by fans. The two were actually married by 1985 after meeting just months earlier. They starred together in the 1986 comedy film Shanghai Surprise in 1986, and Madonna dedicated her 1986 album True Blue to Sean. They ultimately divorced in 1989, and there were rumors of Sean’s domestic violence to be the cause. Madonna has since personally deny those claims. Sean went on to marry (and divorce) Robin Wright, with whom he has two kids. He’s also been linked to Jewel and Charlize Theron. Madonna now has six children, four of which were adopted, and one daughter was with former flame Carlos Leon and one son was with former husband Guy Ritchie.

7. Lenny Kravitz and Nicole Kidman

Back in 2003, before Nicole Kidman was serving up relationship goals with her current husband Keith Urban, she was engaged to musician Lenny Kravitz. When discussing working with Kravitz’s daughter Zoë Kravitz on Big Little Lies, Nicole told Net-A-Porter’s website The EDIT, “Well, I knew Zoë because I was engaged to her father. It’s all in the family! I love Lenny; he’s a great guy.” The two are on good terms today, and Nicole and Lenny posed for photos with Keith backstage at the 2013 .

6. Kim Kardashian and Nick Cannon

Before she was Mrs. Kanye West, Kim Kardashian had a fling with TV host Nick Cannon. The two dated briefly from September 2006 to January 2007, just before her sex tape with Ray J. leaked, which was allegedly a reason for their split. Now married to Kanye, Kim has three children with her husband, and Nick has twins with former wife Mariah Carey.

5. Pink and Joey Fatone

Who saw this one coming? In 2013, Pink told Glamour that she briefly dated *NSYNC member Joey Fatone in the early 2000s. She admitted, “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!” After they quietly ended their romance, Pink went on to marry motocross racer Carey Hart, with whom she has one daughter. Joey married his on-and-off again girlfriend Kelly Baldwin in 2004, and the two have two daughters together.

4. Ryan Gosling and Sandra Bullock

Though they were sixteen years apart when they met on the set of Murder by Numbers in 2002, sparks between Ryan Gosling and Sandra Bullock flew! They dated very briefly, and ultimately ended their romance by 2003. Ryan went on to have two daughters with his longtime partner Eva Mendes, and after a very public divorce from husband Jesse James in 2010, Sandra went on to adopt two children on her own and has since been linked to photographer Bryan Randall.

3. Tom Cruise and Cher

Not one to shy away from talking about her love life, Cher spilled all the details about her former flames on an episode of Watch What Happens Live with Andy Cohen in 2013. When Andy Cohen asked her about her romance with Tom Cruise in the 1980s, Cher said, “He was in the Top 5.” The two allegedly dated just before Tom’s career took off, and in another interview with Oprah Winfrey about their time together, Cher said, “I was crazy about him.” The relationship eventually fizzled out, and Tom went on to marry (and divorce) Mimi Rogers, Nicole Kidman, and Katie Holmes, while Cher went on to marry (and divorce) Sonny Bono and Gregg Allman.

2. Matthew McConaughey and Janet Jackson

Alright, alright, alright! After Matthew McConaughey and Janet Jackson met at the 2002 Grammy Awards, they allegedly hit it off and started a brief romance, though Matthew refused to confirm their relationship, saying they were “just friends.” But in 2006, Janet told Upscale Magazine, “I guess we did [date]. He is a great guy and a sweetheart. It was just for a minute, that’s why I am so hesitant to mention it.” After their short romance, Janet went on to marry Wissam al Manna in 2012. Though they welcomed a child in 2017, they announced their separation shortly after. Matthew married Camila Alves in 2012, and they have three children together.

1. Sarah Jessica Parker and Robert Downey Jr.

It’s SJP and RDJ! Sarah Jessica Parker and Robert Downey Jr. were an item from 1984-1991. The two met while on the set of the drama film Firstborn in 1984 and started dating shortly after. But it was ultimately RDJ’s drug and alcohol addiction that led to their split seven years later. In 2008, he told Parade, “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is. She provided me a home and understanding. She tried to help me. She was so miffed when I didn’t get my act together.” In 1997, SJP married Matthew Broderick, with whom she has twin girls. RDJ married producer Susan Levin in 2005, and they have two kids together (and he has another child from a previous marriage to Deborah Falconer).

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