40+ Celebrity Couples From The Past

Celebrity Couples We Forgot Dated At One Time

For most celebrities, they want to be famous for their talent, but in many cases, it all depends on who you are dating and when. When two huge stars get together, the media is sent into a frenzy. The world waits for every sighting and photo of the pair. However, the “Hollywood Curse” means relationships in the City of Dreams are not to last. But if these celebrities really think we are going to forget about their past romances, then they are mistaken. We are now going to refresh your memory with some of the most famous celebrity relationships from the past that you may have forgotten existed.

1.Nicole Kidman and Lenny Kravitz

Nicole Kidman is known to pack on the PDA with her singer husband, Keith Urban. However, before Keith, and even Tom Cruise for that matter, Kidman was once engaged to musician Lenny Kravitz.

Nicole Kidman and Lenny Kravitz

While the former couple was engaged in 2003, the Stepford Wives star went on to explain that she “wasn’t ready” to get married, so the pair never did. However, Nicole Kidman has since gone on to star alongside Kravitz’s daughter, Zoe, in the hit series, Big Little Lies.

2.Sandra Bullock and Matthew McConaughey

After starring alongside one another in A Time to Kill, Sandra Bullock and Matthew McConaughey started dating. It’s hard to remember a time before McConaughey was married to Camilla Alves, with the pair being envied for their beautiful romance, as well as their beautiful looks.

Sandra Bullock and Matthew McConaughey
Sandra Bullock And Matthew McConaughey

However, four years before tying the knot, McConaughey spoke of his romance with Bullock to Playboy stating, “She’s not a little girl. She’s a woman.” He continued to speak highly of his then-beau expressing, “She could run a country.”

3.Ryan Reynolds and Alanis Morissette

Ryan Reynolds and his current wife, Blake Lively, have proven they are “couple goals” on their respective social media pages. However, before meeting the Gossip Girl star, marrying her, and having two children, the Deadpool actor dated Alanis Morissette.

Ryan Reynolds and Alanis Morissette
Ryan Reynolds and Alanis Morissette

The Canadian actor and the Canadian singer met in 2002 and continued to date for the next four years. In fact, Reynolds had proposed to the “Ironic” singer, but the couple never said their “I do’s.” Rather, they parted ways in 2006.

4.Reese Witherspoon and Jake Gyllenhaal

It was a sad time for Reese Witherspoon when her marriage to the father of her kids, Ryan Philippe, broke down. However, fans rejoiced when it was reported that Witherspoon began dating the very handsome Jake Gyllenhaal.

Reese Witherspoon and Jake Gyllenhaal

The two megastars met while on the set of the movie Rendition in 2007, and sparks began to fly. They officially became a couple soon after but, it was only to last two years since the Big Little Lies star and the Brokeback Mountain actor ended in 2009.

5.Mila Kunis and Macaulay Culkin

While starring on That ’70s Show, Mila Kunis was dating Home Alone star, Macaulay Culkin. The couple began dating in 2002 and were a couple for the next eight years.

Mila Kunis and Macaulay Culkin

6.Leonardo DiCaprio and Gisele Bündchen

He is one of the world’s most famous bachelors, and we still wait to see which woman manages to sweep Leonardo DiCaprio off his feet. It is hard to tell since he once dated the one-time highest-paid supermodel, Gisele Bundchen.

Leonardo DiCaprio and Gisele Bundchen

Before marrying top football star, Tom Brady, Gisele dated Leo on and off for almost six years. Although they made a beautiful couple, it was not to last. Perhaps Leo is pulling a George Clooney and will get married in his 50s.

7.Blake Lively and Penn Badgley

We may have mentioned that Ryan Reynolds and Blake Lively were total “couple goals” but, at one point in time, the world was rooting for Blake Lively and her co-star, Penn Badgley.

Blake Lively and Penn Badgley

Not only were the two co-stars, but they were also each other’s love interest on Gossip Girl. Having gone from an on-screen relationship to an off-screen one, fans of Gossip Girl rejoiced at the news. After three years of dating, the pair called it quits in 2010 but, thankfully, they ended up together on Gossip Girl.

8.Bradley Cooper and Renée Zellweger

Bradley Cooper is on every girl’s radar but has officially been off the market since 2015. However, before meeting his current girlfriend and mother of his child, Irina Shayk, he was dating actress Renée Zellweger.

Bradley Cooper and Renée Zellweger
Bradley Cooper and Renée Zellweger

The pair met on the set of the 2006 thriller, Case 39, but began dating in 2009 when the film was released. After months of media speculation on the status of their relationship, the couple refused to ever speak about it, but would make appearances together. In 2011, the former couple called it quits.

9.Lindsay Lohan and Samantha Ronson

After her relationship with That ’70s Show star, Wilmer Valderrama, ended, Lindsay Lohan dated Hard Rock Cafe heir Harry Morton in 2006. Following their breakup, The Parent Trap star became linked to British DJ, Samantha Ronson.

Lindsay Lohan And Samantha Ronson

The pair began dating in 2008, but the high-profile relationship ended between the actress and the musician in 2009. Speaking of her relationship, Lohan told Us Weekly that their romance was not to last because “Two toxic people cannot be together. End of story.”

10.Angelina Jolie and Jonny Lee Miller

Angelina Jolie has certainly made her fair share of media headlines due to her relationship choices, not to mention her scandals and affairs in the process.

Angelina Jolie and Jonny Lee Miller
Angelina Jolie and Jonny Lee Miller

However, before her high profile marriage to her Mr & Mrs Smith co-star, Brad Pitt, Jolie was married to Jonny Lee Miller. Similarly to her and Pitt, the former couple met on the set of their film, Hackers, in 1995. They were married a year later in March 1996 but split up three years later in 1999.

11.Michael Keaton and Courtney Cox

She is best known for playing Monica Geller on the hit sitcom, Friends, but before becoming one of the most well-known and highest paid actresses for this role, Courtney Cox was in a relationship with Michael Keaton.

Michael Keaton and Courtney Cox
Michael Keaton and Courtney Cox

In fact, Keaton and Cox dated for over six years, before splitting up in 1995. This was just one year after she first appeared as a leading character on the NBC sitcom, and she later went to marry David Arquette. They share one child together but have since divorced.

12.Sarah Jessica Parker and Robert Downey Jr.

Sarah Jessica Parker has nothing but beautiful words to say about her current husband, Matthew Broderick, but she did have another serious relationship before meeting her soulmate.

Sarah Jessica Parker and Robert Downey Jr.

In fact, the Sex and the City star dated fellow actor Robert Downey Jr. before they split up in 1991. The pair were together for seven years before putting an end to their relationship, and the reason for the breakdown of their relationship was the actor’s struggles with addiction at the time.

13.Kim Kardashian and Nick Cannon

Kim Kardashian is now famously married to rapper and singer Kanye West, with the world watching her and her family’s every move. However, before we were all Keeping Up with the Kardashians, Kim was trying to keep up with Nick Cannon.

Kim Kardashian and Nick Cannon

The pair began dating in September 2006 before Kim Kardashian was one of the most famous women alive, but it was only to last four months. The pair called it quits in January 2007 and Cannon later went on to marry, and divorce, Mariah Carey.

14.Michelle Rodriguez and Zac Efron

When it was reported that Michelle Rodriguez and Zac Efron were an item, everyone labeled them to be an unlikely pair. With Rodriquez being ten years older than the High School Musical star, not many people saw this relationship coming.

Michelle Rodriguez and Zac Efron
Michelle Rodriguez and Zac Efron

They proved everyone right since they dated for just two months before a “very mutual” split. Perhaps the fact that Rodriguez got into a relationship with model Cara Delevingne that same year had something to do with it.

15.Orlando Bloom and Kate Bosworth

Orlando Bloom is another actor most girls swoon over whenever he comes on screen, but some lucky ladies have had the opportunity to date the Pirates of the Caribbean star.

Orlando Bloom and Kate Bosworth
Orlando Bloom and Kate Bosworth

While he is most famous for being married to the beautiful Victoria’s Secret model, Miranda Kerr, in 2010, he was previously in a relationship with Kate Bosworth. The Blue Crush star dated the handsome actor for two years before ending it in 2005. Kate, however, is just more proof that Orlando dates beautiful ladies.

16.Ben Affleck and Gwyneth Paltrow

Before marrying a successful British singer, it seems that Gwyneth Paltrow was into leading Hollywood men. While things didn’t work out with Brad Pitt, she also dated Good Will Hunting actor, Ben Affleck.

Ben Affleck and Gwyneth Paltrow
Ben Affleck and Gwyneth Paltrow

The famous pair began dating in 1997 for two years until 1999, before getting back together briefly and ending things for good in 2000. “He’s super intelligent and really, really talented and he’s funny,” Paltrow told Howard Stern. “But he wasn’t in a good place in his life to have a girlfriend.”

17.Mark Ronson and Rashida Jones

Mark Ronson is famous for producing hits such as “Uptown Funk” by Bruno Mars and “Valerie” by Amy Winehouse, so it is no surprise Rashida Jones was once attracted to such a talented star.

Mark Ronson and Rashida Jones
Mark Ronson and Rashida Jones

Ronson and Jones dated from 2002 to 2004 and were even engaged at one point. Ronson proposed to the actress after one year together, by creating a crossword puzzle with the message “Will you marry me.” Their engagement lasted one year and was called off at the same time as their relationship.

18.Usher and Rozonda “Chilli” Thomas

Usher and Rozonda “Chilli” Thomas were both big names during the early 2000s thanks to their respective singing careers, but they became a power duo when they became romantically linked.

Usher And Rozonda “Chilli” Thomas

The singers began dating in 2001, and Rozonda even starred in Usher’s video for his single “U Got It Bad” that same year. However, the pair were reported to have broken up in 2003 because of Usher’s infidelity, although the TLC singer said, “We broke up because I guess it was that time or whatever.”

19.Justin Timberlake and Jenna Dewan-Tatum

She may have been in one of Hollywood’s favorite marriages before parting ways with her husband of ten years, Channing Tatum, but before she even met her former husband, Jenna Dewan was linked to Justin Timberlake.

Justin Timberlake And Jenna Dewan-Tatum

Back in 2002, Jenna was a backup dancer for the “Cry Me a River” singer, and it was also around the same time that Timberlake’s relationship with Britney Spears ended. “We dated…yeah,” Jenna told Andy Cohen. “We were like friends that then dated….I was not the rebound!”

20.Seal and Tyra Banks

Many people are most likely to remember Seal’s high-profile marriage to model Heidi Klum. However, before the singer even met the German beauty, he dated another top supermodel.

Seal And Tyra Banks

It seems Seal had a thing for models since he briefly dated Tyra Banks in 1996. While Tyra Banks has not proven to be so lucky in love since their brief romance, Seal went on to marry Heidi Klum in 2005, and their marriage lasted nine years before their divorce was finalized in 2014.