© Getty Images

Julia Fox and Drake -

The eccentric Julia Fox recently appeared on 'Watch What Happens Live With Andy Cohen' in January 2023 where she dished on the best date she's ever had. She described cuddling on a private jet before landing to go and buy Chanel bags, stating "it was just great." Fox confirmed that it was an A-lister but wouldn't reveal the name, until fans cut to the chase! "Everyone wants to know if it was Drake that took you on that date," Cohen asked her. "Maybe... shouldn't have given me that shot," she said with a sigh.

© Getty Images

Catherine Ommanney and Prince Harry -

Former 'The Real Housewives of DC' star Catherine Ommanney recently told the Sun that she had a fling with Prince Harry when he was 21 and she was 34. 

Ommanney said the pair met through mutual friends in 2006 at the Art Bar in London where she poked fun at his "Australian-style hat" and they hit it off. "Once we started talking, it was like there was no one else was in the room.” They went to a friend's house afterward where they allegedly starting play fighting, and when it was time to go, Ommanney said, "he lifted me by my waist off the floor and held me against the wall. He gave me the most incredible, passionate kiss I have ever had in my life.” They apparently only went on a few dates before calling it off. “Without being arrogant, I think we both quite fancied each other even though he was way too young for me,” she said, adding that she nicknamed him “Baby” because he was fond of lollipops. “If he wasn’t a royal and was maybe 10 years older, he would be my perfect man.”

© Getty Images

Danielle Fishel and Lance Bass -

In a combination that could never even happen today, NSYNC's Lance Bass and 'Boy Meets World' star Danielle Fishel are reminding everyone of their past relationship—by turning it into a film. “Lance and I are actually working on a movie about our love story and about our prom experience,” Fishel explained on a 2022 episode of the 'Pod Meets World' podcast which featured Bass as a guest. “I dated Lance for about a year while I was on ‘Boy Meets World.’ It was my senior year and Lance came with me to my high school prom.”

They revealed that they met on a live special of 'Boy Meets World' where NSYNC came on as guests in 1999. Bass developed a crush on Fishel, got Justin Timberlake to ask her for her number for him, and then they began dating while the band was on tour and the actress was filming. Fishel's prom was a big event, however, as the pair had gotten a hotel room and she had high hopes. “I thought I was going to marry Lance. I had envisioned our future,” she said, but their relationship lacked "intimacy in the romantic sense."

Bass, who came out as gay publicly in 2006, noted that the prom was a big turning point for him. “The reason we wanted to make this prom story into a film, I think so many people can relate to that story; so many people in the LGBT community, their prom night was the night they were like, ‘Oh, wait a minute. This can’t happen anymore,'” he said. “This was the catalyst for me that made me start to accept myself, which took a long time after that, but that was definitely the first little straw that broke.”

They broke up soon after and Fishel was devastated for a while, even shooting down her mother's suggestion that Bass might be gay. “I held on for hope for way too long that we were going to get back together and get married and have a family. … It turns out I’m not Lance’s type.” Luckily the pair remained friends after Bass came out to her. 

© Getty Images

Dax Shepard and Ashley Olsen -

In a combination we'd never even imagine, Dax Shepard revealed that he once dated Ashley Olsen. In a 2022 episode of his podcast Armchair Expert he told co-host Monica Padman, "I dated Ashley Olsen and she's just the most wonderful person. She's fantastic." He acknowledged that even at the time some people thought they were "a pretty weird pairing," but he said she's really "just super funny and sarcastic and intelligent."

And, of course, he was also "kind of thunderstruck with the beauty" when he met her at a party. The actor admitted that prior to the meeting, and very importantly, he had never watched 'Full House,' because, he explained, "I probably wouldn't have been able to be attracted to Ashley if I knew her as a baby."

As for her current success in fashion, Shepard noted that while they dated she was invested into the launch of her and her sister's line The Row. 

And regarding what the former couple actually bonded over? Shepard says part of it was a love of cars. Ashley apparently owned a black Cadillac DeVille DTS when they were dating, and Shepard noted, "I wouldn't mind reconnecting with her to find out if she has that DTS." 

© Getty Images

Martha Stewart and Anthony Hopkins -

In an episode of 'The Ellen DeGeneres Show,' Martha Stewart revealed that she once dated Sir Anthony Hopkins. If their relationship had lasted, they would have been a power couple for the ages. Sadly, Stewart was forced to end things for a very odd, yet understandable, reason. Although Stewart didn't share the year they dated, it was likely in the '90s when Hopkins became famous for playing Hannibal Lector in 'The Silence of the Lambs' (1991). Stewart was forced to break up with him because she couldn't stop thinking of his cannibalistic role! "I have a big, scary house in Maine that's way by itself on a hundred acres in a forest and I couldn't even imagine taking Anthony Hopkins there," she explained. "I couldn't because all I could think of was him eating, you know …" 

© Getty Images

Sandra Bullock and Ryan Gosling - Their romance began when they met on the set of 'Murder By Numbers' (2002), but the relationship didn't last long.

© Getty Images

Ashton Kutcher and January Jones - Do you remember these actors dating from 1998 until 2001?

© Getty Images

Cher and Tom Cruise - The singer and the action star hooked up in the 80s. Tom was only beginning his career when they met, while Cher was 16 years older.

© Getty Images

Ryan Reynolds and Melissa Joan Hart -

Melissa Joan Hart, best known for starring in the Nickelodeon shows 'Sabrina the Teenage Witch' and 'Clarissa Explains It All,' recently opened up about some of her '90s romances. Before 'Sabrina the Teenage Witch' started its seven-season run, Hart appeared in a movie of the same name. Ryan Reynolds starred opposite her as Sabrina's love interest, Seth, when they were both 19 years old. According to Hart, the pair were "smitten" with each other. "He was adorable. He was a really nice guy," she recalled. However, she had a boyfriend at the time so she never really took the leap with Reynolds. She reflected that "he would have been a great boyfriend. And I didn't end up with the other guy, so maybe I should have taken a chance!"

Although the pair never made a serious go of it, they did share a steamy kiss on the last day of shooting. "I chased him down, got in front of his car and just kissed him and then made out with him all night," Hart admitted. "Then I had to call my boyfriend the next day and explain it."

© Getty Images

Ryan Reynolds and Alanis Morrisette - A lot of people have forgotten but they were together at the start of the 2000s. The relationship did last for five years, though.

© Getty Images

Emily VanCamp and Chris Pratt - They played siblings on the series 'Everwood' (2002-2006), but off camera they were in a romantic relationship!

© Getty Images

Justin Timberlake and Fergie - This was certainly a while ago! It was even before Justin and Britney Spears got together. JT was only 16 at the time, while Fergie was part of the group Wild Orchyd.

© Getty Images

Jared Leto and Cameron Diaz - This one got lost among their long list of relationships. But it actually lasted quite a while: the pair dated for four years before breaking up.

© Getty Images

Wynona Ryder and Matt Damon - This relationship was kept on the down-low, but they were together for two years. This photo is from 1999!

© Reuters

Megan Fox and David Gallagher - Since 2010, Fox has been married to Brian Austin Green, but she dated David Gallagher from '7th Heaven' a long time ago.

© Getty Images

Michael Jackson and Madonna - You probably heard of this one. The King and Queen of Pop had a relationship which was confirmed by the two.

© Getty Images

Matthew McConaughey and Janet Jackson - They had a quick fling in 2002. It didn't work out but they remained friends.

© Getty Images

Daniel Day-Lewis and Julia Roberts - It is said that Day-Lewis was the reason for the split between Julia Roberts and Kiefer Sutherland. Daniel and Julia dated in the early 90s. Remember that?

© Getty Images

Juliette Lewis and Johnny Depp - Juliette Lewis met Johnny Depp after ending her relationship with Brad Pitt. The dated in the early 90s but it didn't last. They're still good friends - this photo is from 2016!

© Getty Images

Bradley Cooper and Zoe Saldana - They started dating in December 2011 while filming 'The Words,' but split in March of the following year. Six months later, they got back together but it didn't last.

© Getty Images

Jack White and Renée Zellweger - They were together for almost two years. Before this, the star of 'Bridget Jones's Diary' dated Jim Carrey too!

© Getty Images

Robert Downey Jr. and Sarah Jessica Parker - Iron Man and the star of 'Sex and the City' formed quite the power couple from 1984 until 1991.

© Getty Images

Salma Hayek and Edward Norton - They dated for three years until splitting in 2000.

© Getty Images

Will Smith and Tyra Banks - Tyra was Will's onscreen girlfriend in 'Fresh Prince of Bel-Air' but they also dated in real life during the 90s.

© Getty Images

Seal and Tyra Banks - The singer has a weakness for models. Before marrying German supermodel Heidi Klum, the British 'Kiss From a Rose' singer dated Tyra Banks in 1996.

© Getty Images

Matthew Perry and Julia Roberts -

Matthew Perry reflects on his unexpected and short relationship with Julia Roberts in his book 'Friends, Lovers and the Big Terrible Thing,' which of course began with 'Friends.' 

“Julia had been offered the post-Super Bowl episode in season 2 and she would only do the show if she could be in my story line,” writes Perry, as per ET. “Let me say that again—she would only do the show if she could be in my story line. (Was I having a good year or what?) But first, I had to woo her.” He revealed that he sent Roberts three dozen roses and a note that read, "The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers.”

In a surprising move, Perry recalled, "her reply was that if I adequately explained quantum physics to her, she’d agree to be on the show.” He sent her a paper the next day about "wave-particle duality" and "the uncertainty principle and entanglement" and Roberts agreed to do the show, while also sending him tons of bagels.

They started dating shortly after, but to Perry it felt doomed. "Dating Julia Roberts had been too much for me,” he wrote. “I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable.”

And so, it was Perry who ended the relationship. “Instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts. She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her," he wrote. "I can’t begin to describe the look of confusion on her face.”

© Getty Images

Penélope Cruz and Tom Cruise - Their relationship began in 2001 after Cruise split from Nicole Kidman. They met filming 'Vanilla Sky' and dated for three years.

© Getty Images

Lenny Kravitz and Nicole Kidman - The rocker/actress couple were together from 2003 to 2005. It ended amicably and Kravitz gets on well with Kidman's husband, Keith Urban.

© Getty Images

Helen Mirren and Liam Neeson - They admitted to being in a relationship for five years from 1980 to 1985, and even lived together.

© Getty Images

Michelle Rodriguez and Cara Delevingne - The 'Fast & the Furious' star dated the British model for around four months.

© BrunoPress

Michelle Rodriguez and Zac Efron - Before she dated Cara Delevignge, Rodriguez dated Hollywood hunk Zac Efron.

© BrunoPress

Kirsten Dunst and Jake Gyllenhaal - They met each other in 2002 and dated for two years. Gyllenhaal also dated Natalie Portman for a while.

© Getty Images

Moby and Natalie Portman - In 2001, the actress had a brief romance with musician and producer Moby.

© Getty Images

Owen Wilson and Sheryl Crowe - Crowe has also dated Eric Clapton and Lance Armstrong, while Owen Wilson was involved with Kate Hudson.

© Getty Images

Jason Lewis and Rosario Dawson - The 'Sex and The City' actor was in a relationship with Rosario Dawson for a long time!

© Getty Images

50 Cent and Chelsea Handler - This is a truly unlikely couple, but they had a brief relationship, and the presenter even shared photos together with 'Fiddy' on social media.

© Getty Images

Lara Flynn Boyle and Jack Nicholson -

The age difference of 33 years wasn't an obstacle in this relationship.

See also: Celebrities dish on their biggest dating deal-breakers

© Getty Images