Celebrity Pairings That Almost Nobody Remembers Happened

For some reason, we are all incredibly invested in the love lives of our favorite stars. Perhaps because they are all impossibly good looking, wealthy, and it’s just so much fun to keep track of their sordid love affairs. The fact is, most Hollywood relationships don’t last forever, and most of us are eager to hear who they move on with. Some couples that were once Hollywood staples have been all but forgotten. Here are some amazing celebrity couples that will have you exclaiming, “wow, they used to date?”

Julia Roberts and Liam Neeson

Two of Hollywood’s most respected actors, Julia Roberts and Liam Neeson used to be in a relationship. They began their relationship in 1988 after they met on the set of the film Satisfaction. They lasted until 1990, and went on to marry other people.

Although you might associate Nicole Kidman with her longtime beau Keith Urban, before they two were married, and even before she was with Tom Cruise, she was once betrothed to none other than Lenny Kravitz. They got engaged in 2003, but Kidman explains that at the time she was not ready to tie the knot. Years later, Kidman went on to star alongside Kravitz’s daughter Zoe on the hit show Big Little Lies.

After Tom Cruise and Nicole Kidman divorced, Cruise met Penelope Cruz while they were filming the film Vanilla Sky in 2000. They stayed together until 2004, and everyone was sad that Cruise and Cruz were no more. He went on to marry Katie Holmes in 2006 and Cruz married Javier Bardem in 2010.

Although now we associate Ryan Reynolds with no one but wife Blake Lively, he has had several high profile relationships before. In 2002, he met fellow Canadian Alanis Morissette and the two began dating. They lasted for four years and broke off their engagement in 2006.

Speaking of Blake Lively, before she was married to Ryan Reynolds, she was once linked to her Gossip Girl co-star and on-screen love interest, Penn Badgley. Fans of the show could not get enough of their real life romance, but in 2010, the two decided to part ways. However, their on-screen characters remained together, so fans could at least have that.

Yet another on-screen relationship that turned to real life romance was the one involving Alexis Bledel and Milo Ventimiglia who played Rory Gilmore and Jess Mariano on Gilmore Girls. The actors began dating off-screen in 2003 and their romance lasted for three years before they ended up breaking up. Bledel is now married to actor Vincent Katheiser.

In 2003, after Justin’s infamous breakup with Britney Spears, Justin Timberlake began dating actress Cameron Diaz, who was eight years his senior, which in Hollywood might as well be a lifetime. The two were one of the most popular couples in the tabloids, but the ended up breaking it off in 2007. She is now married to Good Charlotte band member Benji Madden and Timberlake is married to actress Jessica Biel.

Courteney Cox is best known for her role as Monica Geller on beloved sitcom Friends. Before she was a household name however, she dated actor Michael Keaton, 13 years her senior. They two were together for six years, breaking up in 1995. She then moved on with David Arquette, who she ended up marrying and later divorcing. She is currently linked to Snow Patrol band member Johnny McDaid.

Kim Kardashian has had several high profile relationships, but most will not remember a time when she was linked to Nick Cannon. They started dating in September 2006, before she was one of the most famous people on earth. They dated for just four months, their relationship ending in January 2007. He later married Mariah Carey, and then they divorced. Kardashian was famously married to rapper Kanye West, but has since filed for divorce.

Gwenyth Paltrow has dated many a famous Hollywood leading man. She famously dated Brad Pitt and she was also linked to Ben Affleck. They started dating in 1997 before breaking up for the first time in 1999. They got back together only ti break up for good in 2000. Paltrow told Howard Stern: “He’s super intelligent and really, really talented and he’s funny. But he wasn’t in a good place in his life to have a girlfriend.” She went on to marry and divorce Chris Martin of Coldplay fame, while Affleck married and later divorced actress Jennifer Garner.

Zac Efron dated fellow actress Michelle Rodriguez, who is ten years his senior. Many people raised an eyebrow at the age difference and were surprised by the relationship. Their romance lasted just four months, with what they called a “very mutual” breakup. Shortly after, Rodriguez was in a relationship with model Cara Delevigne.

Orlando Bloom and Kate Bosworth

Orlando Bloom rose to fame after starring in successful franchises Lord of the Rings and Pirates of the Caribbean. Before his marriage to Victoria’s Secret model Miranda Kerr, Bloom was linked to Blue Crush actress Kate Bosworth. The two dated for two years before breaking up in 2005. Now Bloom is linked to pop star Katy Perry. Bosworth  married film director Michael Polish in 2013.

Before Jessica Biel married Justin Timberlake, she had several high profile relationships. Towards the end of her time on Seventh Heaven, Biel began to date Chris Evans. They dated from 2001 and had an on-and-off again relationship until 2006. After their relationship fizzled, she met and later married Timberlake.

In the early 2000’s, Usher and Rozonda “Chilli” Thomas (of TLC fame) were at the peak of their pop star careers. It seemed inevitable when the two came together to form a power couple. The two started dating in 2001 and she starred in his music video for “U Got It Bad.” They lasted until 2003. On their breakup, Thomas said: “We broke up because I guess it was that time or whatever.”

Back in 2002, Justin Timberlake and Britney Spears went through a very public breakup. Before he moved on to Cameron Diaz, Timberlake was briefly linked to Jenna Dewan, who was one of his backup dancers. Dewan told Andy Cohen: “We dated…yeah. We were like friends that then dated….I was not the rebound!” She was later married to actor Channing Tatum, but the two divorced after ten years of marriage.

After breaking up with That 70’s Show actor Wilmer Valderrama, Lindsay Lohan moved on with heir to the Hard Rock Cafe empire Harry Morton. Once they broke up, she began a relationship with British DJ Samantha Ronson. They started dating in 2008, but it only lasted until 2009. Of the relationship, Lohan said: “Two toxic people cannot be together. End of story.”

While most people associate Seal with his previous high profile marriage to model Heidi Klum, he previously dated another supermodel. In 1996, he was briefly linked to Tyra Banks. After they broke up, Seal and Klum got together and were married for nine years. Banks never married but she has a son with former partner Erik Asla.

Way back in high school, actress Scarlett Johansson dated musician Jack Antonoff. They dated when they were 17 and even went to prom together. Antonoff was later linked to Lena Dunham, though the two have since broken up. Johansson was married to Ryan Reynolds, then married to Romain Dauriac, and is currently married to Colin Jost.

In 2010, actors Aubrey Plaza and Michael Cera started dating after meeting on the set of SCott Pilgim vs. the World. Plaza shared: “We drove across the country after we shot that movie and almost got married in Vegas.”  They were together for more than a year when they broke up. Plaza has been with director and writer Jeff Baena since 2011.

Shalane McCall is best known for her role as Charlotte “Charlie” Wade on soap Dallas. In 1987, Brad Pitt had a four episode arc on the show, where he met McCall. At the time, he was 24 and she was just 15, but the two had a brief relationship. She later went on to marry musician Trent Valladares, and Pitt famously was with Jennifer Aniston and then Angelina Jolie.

Sandra Bullock and Ryan Gosling began dating in 2002 after meeting on the set of film Murder By Numbers and their relationship lasted for a year before calling it quits. Back then, their 16 year age difference caused quite a stir. Gosling later dated Rachel McAdams and since 2011 has been dating Eva Mendes, who he shares two children with. Bullock went on to marry Jesse James, and the two divorced several years later.

Pop icon Madonna was famously linked to director Guy Ritchie, but before their marriage began, Madonna was briefly linked to basketball star Dennis Rodman in 1994. Their two month affair was highly publicized before they ended things. He later went on to date and briefly marry Carmen Electra.

In 1999, Cameron Diaz dated 30 Seconds to Mars frontman and actor Jared Leto. Their relationship lasted until 2003, and it was rumored that the two were even engaged at one point. However, they ended their relationship and Diaz went on to marry Benji Madden. Leto has never married.

After a six year long marriage to Cynthia Scurtis, baseball star Alex Rodriguez began dating actress Kate Hudson in 2009. The relationship lasted just seven months. Hudson went on to marry musician Chris Robinson, and later was married to Matt Bellamy. She is currently linked to musician Danny Fujikawa. Rodriguez began dating Jennifer Lopez in 2017 and the two got engaged in 2019.

Although Lamar Odom’s most high profile relationship was his marriage to Khloe Kardashian, she is not the only famous woman he has been linked to. In 2009, he began dating actress Taraji P. Henson. He said he regrets the way things ended with them and that he “didn’t know how to tell her that I was falling in love with another woman named Khloe Kardashian.” Henson was engaged to NFL player Kelvin Hayden in 2018, but the two have since ended their engagement.

Wilmer Valderrama dated Lindsay Lohan and more recently was linked to pop star Demi Lovato. In 2001, Valderrama was linked to actress Mandy Moore until 2002. Moore went on to date actor Zach Braff before marrying musician Ryan Adams. The two ended up divorcing. Valderrama is now engaged to model Amanda Pacheco, and their first daughter was born in February 2021.

In 1985, pop icon Cher and actor Tm Cruise were engaged in a short-lived fling that many never even knew about. Cher was previously married to her musical partner Sonny Bono, while Tom Cruise later went on to marry and then divorce Nicole Kidman and Katie Holmes. Cher later married Gregg Allman of the Allman Brothers, but the pair divorced after a few years.

Although Selena Gomez is best known for dating musicians Justin Bieber and The Weeknd, she also dated another famous singer. Before her other high profile relationships, she was briefly linked to Nick Jonas of the Jonas Brothers, and she even appeared in their music video for their single “Burnin’ Up.”

Justin Timberlake has been linked to many famous women, and one of them is Alyssa Milano. Right after his breakup with Britney Spears, the two began to date. Milano shared that”  “Right after Britney broke his heart, I swooped in for the kill!” After they broke up, he went on to date Cameron Diaz and then marry Jessica Biel.

Back in 2002, comedian David Spade and actress Julie Bowen dated for about a year before breaking up. Spade was infamously linked to many actress included Heather Locklear, Teri Hatchers, and Naya Rivera. E! News referred to him as “a bachelor-era George Clooney of the comedy world.” Bowen went on to marry real estate investor and software developer Scott Phillips in 2004 before divorcing in 2018.

In 2013, Rosario Dawson and Danny Boyle were spotted together and the rumors began to swirl about the pair. She appeared in the film Trance, which Boyle directed. She later shared that: “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup.” She later dated Eric Andre and since 2019 has been with senator Cory Booker.

After meeting on the set of an ad campaign, actors Jamie Dornan and Keira Knightley began dating in 2003. They ended up breaking up in 2005, after which both embarked on to highly successful acting careers. Dornan ended up marrying actress and singer Amelia Warner in 2013. Knightley married musician James Righton from the band Klaxons also in 2013.

Although on an appearance on Oprah Chelsea Handler said: “I’m not gonna date somebody whose name is a number,” and much speculation from fans, she later admitted that she was in a relationship with rapper 50 Cent. The relationship did not last long, and Handler went on to date hotelier Andre Balazs, though the two ended their relationship.

Seth MacFarlane is best known as the creator of hit comedy animated series Family Guy. In 2012, MacFarlane is Game of Thrones actress Emilia Clarke began to date, but the two ended up breaking up just six months later. Despite their breakup, the pair have remained on good terms.

In 2011, fans were shocked to hear that Scarlett Johansson and Sean Penn began dating. At the time, Penn was 50 years old and Johansson was just 26 years old, and their huge age difference caused quite a stir. Johansson is now married to Colin Jost. Penn is now married to actress Leila George, who is 32 years his junior.

For a very brief time from December 2012 through January 2013, music mogul Simon Cowell was linked to Playboy star Carmen Electra. She has said of Cowell that he is “awesome and very charming. I just thought Simon was so much fun and was so smart and he’s really interesting.” However, despite this, their relationship did not last. Cowell is now linked to Lauren Silverman.

In 1989, Brad Pitt and Christina Applegate went on their first date. As two young celebrities, of course this date was to the MTV Movie Awards. Applegate shared that she ended up jilting him and leaving him that night to meet with another man. She never shared who the mystery man was that she left Brad Pitt for, but she said that things didn’t work out between them either. She ended up marrying actor Johnathon Schaech and later married musician Martyn LeNoble.

Mark Ronson, who is best known for producing the song “Uptown Funk” with Bruno Mars and “Valerie” with Amy Winehouse was linked to actress Rashida Jones from 2002 until 2004. They were even engaged for a year, but the two decided to call it quits before tying the knot. Jones is now linked to Vampire Weekend frontman Ezra Koenig. Ronson married French actress and singer Joséphine de La Baume in 2011, but the two divorced in 2018.

After starring in Spider-Man in 2002, Kirsten Dunst became the Hollywood “it” girl of the moment. It makes sense that she began dating Jake Gyllenhaal, who was one of the biggest Hollywood heartthrobs of the day as well. They dated from 2002 until 2004. In 2009, Dunst said in Allure about Gyllenhaal: “It would be nice to see him, but we’re not good friends.” Since 2018, he has been dating French model Jeanne Cadieu. Dunst is currently engaged to actor Jesse Plemons.

Ashton Kutcher and January Jones

Of course, most of us associate Ashton Kutcher with his ex-wife Demi Moore and current wife and former That 70’s Show co-star Mila Kunis. However, back in the day before he was a big star, he dated January Jones, who later became known for her role in Mad Men. They dated from 1998 until 2001, before both of them became well known stars.