30 Unexpected Celebrity Couples From The ’80s, ’90s, ’00s, & Beyond

Though they only went on one date in 2006, the evening was highly publicized. “She left about halfway through and went to the restroom and then shockingly there were 25 paparazzi when we left the theater,” Lachey told Andy Cohen in 2019. “I think there were other things in play on our little rendezvous.”

Cruise and Cher met in 1985 at Madonna and Sean Penn’s wedding and reconnected the same year. “A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic,” she recalled. “We didn’t go out till way later, but there definitely was a connection.” Cher said that they were still friends decades after dating.

The actors dated for five years — and starred in movies Cellular and London during their relationship. They apparently became very serious and publicly spoke about their future. “We always talk about [marriage]. We both want to be married, and we both want to have children,” Alba told Cosmopolitan in 2005. The pair split in 2006.

The actors got together while filming Murder by Numbers in 2001. Bullock said that being with Gosling helped her relax. “I live my life at a manic pace, and he’s taught me to disregard all that isn’t important,” she said in 2003. Even though they only lasted two years, Gosling called her one of “the greatest girlfriends of all time.”

Kidman and Kravitz started dating in 2002 when the singer was reportedly the actor’s landlord. At the time, they managed to keep their relationship under wraps, without many knowing that they were engaged. Fifteen years later, Kidman confirmed the rumor that things were that serious and would go on to star in Big Little Lies with Kravitz’s daughter Zoë.

Perry and Roberts were an item around the time when Roberts appeared on Friends in 1995. Though they kept their relationship quiet, Perry revealed in his memoir that they sent each other faxes during their courtship. “It wasn’t uncommon for me to read these faxes three, four, sometimes five times, grinning at that paper like some kind of moron,” he wrote in 2022.

Many fans remember “Hiddleswift” well. After the singer and Marvel star connected at the 2016 Met Gala, they embarked on a whirlwind romance that amounted to a summer fling, complete with Rhode Island escapades and the infamous “I Heart Taylor Swift” tank top. She reportedly wanted to keep things private, while he was more comfortable with a public relationship.

The Friends star started dating Batman in 1989, meeting via a friend who told Keaton she loved him in Clean and Sober. Cox spoke fondly of their relationship not long after their breakup in 1995. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” she told PEOPLE at the time.

SJP and RDJ met on the set of Firstborn and were together from 1984 to 1991. Their relationship ultimately didn’t work out while Downey Jr. was battling a substance use problem. “She provided me a home and understanding. She tried to help me. She was so miffed when I didn’t get my act together,” he said in 2009.

Long before Antonoff was Bleachers’ frontman and Johansson was an Oscar-nominated star, the pair dated in the early aughts when both attended the Professional Children’s School in New York. They even reportedly went to prom together. If this shocks you, you’re not alone — Lena Dunham also apparently didn’t believe the two were an item, either.

The couple reportedly met through Gyllenhaal’s sister Maggie in 2002. Perhaps the most iconic moment of their relationship was when Dunst voraciously inhaled salad while out to lunch with Gyllenhaal (you know the picture). Though they moved in together into a $1.7 million L.A. mansion and adopted a German Shepherd puppy, their love only lasted two years.

The actor and baseball star sparked dating rumors at the reopening of Miami’s Fountainbleau Hotel in 2008. The following year during baseball season, the Almost Famous star wasvspotted in the stands at A-Rod’s games, supporting the athlete through the Yankees’ World Series win in 2009. The two parted ways the following month, as per Us Weekly.

More than 30 years ago, Pitt and Applegate were an item — until she ditched him mid-date at the MTV Movie Awards in 1989 for another man. Though she wouldn’t say who it was on Watch What Happens Live With Andy Cohen in 2015, the following year it was revealed to reportedly have been Sebastian Bach.

The Canadians dated for two years and then engaged for three years before calling it quits in 2007. Morissette told PEOPLE in 2005 that the actor was “like a soul brother” to her, “except that I want to jump his bones.” After their breakup, it’s believed that Morissette wrote the song “Torch” about Reynolds.

The actors got together in 1996 and were quietly together for two years. “No matter where he is in his life or where I am in mine — he could be married — I know we would stay close,” Bullock gushed after their breakup in 2003.

The Gossip Girl co-stars dated from 2007 until 2010, and Badgley hasn’t been afraid to poke fun at their relationship. He joked that the best-onscreen kiss he had was with Lively, “because we actually had a relationship at the time,” and his worst kiss? “Maybe Blake after we broke up.” They kept it professional while wrapping up Gossip Girl.

Perry and Brand met in 2008 on the set of Get Him To The Greek. Though her scene was cut from the movie, the pair started dating and got married in 2010. He reportedly told her he was filing for divorce via text message in 2011. It’s believed that Perry wrote the 2012 song “Wide Awake” about Brand.

Long before Kunis married Ashton Kutcher, she dated Culkin for eight years, until 2011. Though they kept things private, Kunis gave fans a look into their lives. “We enjoy each other’s company. We like to read books or play video games or watch TV or go to the movies,” she said 2007. “And he’s an amazing cook. He makes dinner every night.”

The Playboy icon and singer got together — twice — in the early aughts. At first, the pair were engaged but broke things off in 2003. Three years later, they made it to the altar but she ultimately filed for divorce in late 2006, with her cameo in Borat reportedly being why.

The pair were first connected after flirting at the 2012 HBO Emmys afterparty. Their love didn’t last, reportedly due to distance. “It was really a location challenge,” a source to E! revealed in 2013 when they split. “She has been in Europe shooting Game of Thrones and he is based in California, so it was hard to make it work despite the distance.”

The pair met through Hendricks’ Mad Men co-star Vincent Kartheiser — Hendricks Googled him the night they met — and they got married in 2009. A decade into their marriage, which was filled with Instagram updates about their dogs Zou Zou and Triscuit, Hendricks and Arend called it quits in 2019.

Before Amal Alamuddin, Clooney was married to Balsam from 1989 to 1992. The couple divorced three years later, and Clooney felt at fault. “I just don’t feel like I gave Talia a fair shot." he told Vanity Fair in 1996. Decades after their divorce, Balsam still sings Clooney’s praises. “He remains charming,” she told PEOPLE in 2016.

The couple secretly dated in the ’90s, and not much is known about their relationship beyond Madonna confirming that they were together and teasing that they collaborated together. Tupac, who passed away in 1996, also allegedly sent Madonna a letter when he was in prison, breaking things off with her and implying they were on good terms.

The actors met on the set of Mad Men in 2012, and their co-stars noticed a connection between them. “We were completely professional,” Kartheiser said of their behavior onset, starting to date after Season 5 wrapped filming. They got married in 2014 and had a baby the following year. Kartheiser and Bledel divorced in 2022.

The Tesla CEO and singer made their red carpet debut at the 2018 Met Gala. Their relationship included two babies with unique names and an SNL cameo where Grimes appeared as Princess Peach alongside Musk’s Wario. Grimes revealed in 2022 that they broke up after a Vanity Fair profile that touched on their relationship was published.

Three months after connecting via Saturday Night Live in 2008 the pair were engaged and got married in 2009. Eight months later, Moss filed for divorce, reportedly over clashing work schedules and distance. Armisen blamed himself for the implosion of their marriage. “I think I was a terrible husband, I think I’m a terrible boyfriend,” he said in 2013.

The actors met through their famous BFFs (Ben Affleck and Gwyneth Paltrow) and began appearing in public together after Damon said he and Minnie Driver were no longer together in 1998. Ryder and Damon were together for two years untilvcalling it quits in the spring of 2000.

Blunt and Bublé started dating in 2005 after she visited him backstage at a concert, and they were absolutely obsessed with each other (so was his mom about Blunt). The crooner famously wrote the 2007 song “Everything” about her. Their relationship ended in 2008 amid cheating rumors, though Bublé blamed their schedules.

Skrillex and Goulding started dating in 2011, but they had been friends beforehand. “We were good mates before we became a couple,” Goulding gushed, “and we’re both really big fans of each other.” The pair collaborated on the song “Summit” while dating. Distance led to the musicians’ breakup in 2012.