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Ryan Reynolds and Melissa Joan Hart -

Melissa Joan Hart, known for 'Sabrina the Teenage Witch' and 'Clarissa Explains It All,' shared her '90s romantic experiences. Before her seven-season run on 'Sabrina,' she starred alongside Ryan Reynolds in a movie. They were smitten but couldn't pursue it as Hart was in a relationship. Reflecting, she regrets not taking a chance, as the relationship with her boyfriend at the time didn't last.

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Ryan Reynolds and Alanis Morrisette -

Many individuals have overlooked their previous connection, which began in the early 2000s. Despite this, their relationship persevered for a notable duration of five years.

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Cher and Tom Cruise -

During the 80s, the singer and the action star started dating. Tom, who was at the early stages of his career, crossed paths with Cher, who was 16 years older.

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Ashton Kutcher and January Jones -

Do you recall these actors dating between 1998 and 2001?

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Emily VanCamp and Chris Pratt -

They portrayed siblings on the show 'Everwood' (2002-2006), yet off-screen they were romantically involved!

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Juliette Lewis and Johnny Depp -

Juliette Lewis dated Johnny Depp following her split from Brad Pitt in the early '90s. Although their romance was short-lived, they remained close friends, as evidenced by this photo taken in 2016.

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Danielle Fishel and Lance Bass -

Lance Bass of NSYNC and 'Boy Meets World' star Danielle Fishel are working on a movie about their past romance. They dated for about a year, and Bass even attended Fishel's high school prom, although Fishel was disappointed with the lack of physical intimacy. The relationship didn't last. "I thought I was going to marry Lance," she admitted. "I had envisioned our future."

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Danielle Fishel and Lance Bass -

Lance Bass publicly came out as gay in 2006 and views the prom as a pivotal moment in his life. He believes this resonates with many in the LGBT community as it often marks the realization that they can't hide their true selves any longer. For Bass, it was the catalyst for self-acceptance, although it took time to fully embrace his identity.

After their breakup, Danielle Fishel initially held onto hopes of a future together and dismissed the possibility of Bass being gay. However, their friendship endured even after he confided in her about his sexuality.

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Dax Shepard and Ashley Olsen -

In a surprising revelation on his podcast 'Armchair Expert' in 2022, Dax Shepard disclosed that he had a romantic relationship with Ashley Olsen. Shepard spoke positively about Olsen, describing her as a "wonderful person" with remarkable qualities. Despite their unconventional pairing, Shepard praised Olsen's sense of humor, wit, and intelligence.

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Sandra Bullock and Ryan Gosling -

They first met on the set of 'Murder By Numbers' in 2002, but their romance was short-lived.

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Justin Timberlake and Fergie -

This happened quite some time ago, before Justin and Britney Spears started dating. JT was just 16 years old, while Fergie belonged to the group Wild Orchyd.

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Jared Leto and Cameron Diaz -

This relationship was often overlooked among their numerous other connections. However, it endured for a significant period of time, spanning four years before coming to an end.

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Wynona Ryder and Matt Damon -

This undisclosed relationship lasted for a span of two years and the featured photo dates back to 1999.

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Megan Fox and David Gallagher -

Before marrying Brian Austin Green, Fox had a romance with David Gallagher from '7th Heaven.'

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Michael Jackson and Madonna -

This one is likely familiar to you. The relationship between the King and Queen of Pop was acknowledged by both of them.

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Matthew McConaughey and Janet Jackson -

Their brief romance occurred in 2002, resulting in a failed relationship, yet they remained friends.

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Daniel Day-Lewis and Julia Roberts -

According to reports, Day-Lewis was allegedly the cause of the separation between Julia Roberts and Kiefer Sutherland. Daniel and Julia were in a relationship during the early 90s.

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Bradley Cooper and Zoe Saldana -

They began a relationship in December 2011 during the production of 'The Words,' but sadly broke up in March of the subsequent year. Their reunion took place six months later, but it proved to be short-lived.

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Jack White and Renée Zellweger -

They were in a relationship for nearly two years. Prior to that, the protagonist of 'Bridget Jones's Diary' also dated Jim Carrey!

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Robert Downey Jr. and Sarah Jessica Parker -

The actress from 'Sex and the City' and Iron Man were in a relationship from 1984 to 1991.

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Salma Hayek and Edward Norton -

They were in a relationship for three years, until breaking up in 2000.

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Will Smith and Tyra Banks -

Tyra played Will's girlfriend on 'Fresh Prince of Bel-Air' and they also had a real-life relationship during the 90s.

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Seal and Tyra Banks -

The vocalist has a fondness for models. Prior to tying the knot with German supermodel Heidi Klum, the British singer of 'Kiss From a Rose' had a relationship with Tyra Banks in 1996.

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Martha Stewart and Anthony Hopkins -

Martha Stewart revealed on 'The Ellen DeGeneres Show' that she had a romantic relationship with Sir Anthony Hopkins, likely in the 1990s when Hopkins gained fame for his portrayal of Hannibal Lecter in 'The Silence of the Lambs' (1991). However, Stewart ended the relationship due to her inability to escape the haunting image of Hopkins' cannibalistic character and couldn't imagine bringing him to her remote Maine residence!

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Penélope Cruz and Tom Cruise -

Tom Cruise started dating Penelope Cruz in 2001 following his separation from Nicole Kidman. They got acquainted while working on the movie 'Vanilla Sky' and were in a relationship for three years.

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Lenny Kravitz and Nicole Kidman -

The couple were in a relationship from 2003 to 2005. Their split was friendly and Kravitz also maintains a good relationship with Keith Urban, Kidman's husband.

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Julia Fox and Drake -

When Julia Fox appeared on 'Watch What Happens Live With Andy Cohen' in January 2023, she hinted that her best date of all time was with Drake. She recounted cozying up on a private jet and shopping for Chanel bags.

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Helen Mirren and Liam Neeson -

They confirmed being in a relationship for five years, from 1980 to 1985, and lived together too.

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Michelle Rodriguez and Cara Delevingne -

The British model and 'Fast & the Furious' star were in a relationship for approximately four months.

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Michelle Rodriguez and Zac Efron -

Rodriguez previously dated actor Zac Efron before being with Cara Delevingne.

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Kirsten Dunst and Jake Gyllenhaal -

They crossed paths in 2002 and were in a relationship for a couple of years. Gyllenhaal also had a brief romance with Natalie Portman.

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Moby and Natalie Portman -

The actress briefly dated musician and producer Moby in 2001.

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Catherine Ommanney and Prince Harry -

Former star of 'The Real Housewives of DC' Catherine Ommanney revealed a brief romantic involvement with Prince Harry when he was 21 and she was 34. They met in 2006 through mutual friends, and after some playful interactions and a passionate kiss, they went on a few dates. However, their age difference and Harry's royal status played a role in their decision to part ways. 

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Owen Wilson and Sheryl Crow -

Crowe has also been romantically linked to Eric Clapton and Lance Armstrong, while Owen Wilson was once in a relationship with Kate Hudson.

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Jason Lewis and Rosario Dawson -

The actor from 'Sex and The City' had a long-term relationship with Rosario Dawson.

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50 Cent and Chelsea Handler -

Despite being an unexpected pair, they briefly dated and the presenter posted pictures alongside 'Fiddy' on social media.

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Matthew Perry and Julia Roberts -

In his memoir 'Friends, Lovers and the Big Terrible Thing,' Matthew Perry reflects on his brief romance with Julia Roberts during the second season of 'Friends.' He won her over with roses and a paper explaining quantum physics, which secured her appearance on the show. They began dating, but Perry felt overwhelmed and insecure in the relationship, ultimately ending it to avoid the pain of being dumped. Perry's insecurities played a significant role in their short-lived romance, despite Roberts' initial interest in him.

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Lara Flynn Boyle and Jack Nicholson -

The 33-year age gap did not hinder this relationship. 

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

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