Rachel M. Johnson is a lover of all things pop culture. She's been writing about music and entertainment online for over two years.
Celebrity couples seem to come and go, and many times these romantic flings never seem to last. Hollywood can often be a breeding ground for random and strange couplings, and some of those pairs have downright baffled us! From random dates to long term relationships, here's a list of some of the most wild and odd celebrity couples.
Cher & Tom Cruise
Music icon Cher and global film star Tom Cruise had a brief fling in 1985, long before the actor became a Hollywood hunk. Cher had revealed to Andy Cohen's on Bravo's Watch What Happens Live that Cruise, "was in the Top 5" for her list of best lovers. The unlikely pair met in 1985 at Madonna and Sean Penn's wedding, and once again at an event focusing on dyslexia. Cher would go on to recall, "A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic. We didn't go out till way later, but there definitely was a connection there."
Did You Know? Tom Cruise was 16 years Cher's junior when the pair dated in 1985; Cruise was born in 1962 and Cher in 1946.
Winona Ryder & Matt Damon
At the end of the 90s, actress Winona Ryder was a beloved film star with a very successful resume. Matt Damon was an up-and-coming actor who was on the cusp of major stardom with his soon-to-be-released Oscar winning film, Good Will Hunting. The couple were introduced at a New Year's Eve party in 1997, by their (then) best friends Gwyneth Paltrow and Ben Affleck (the two were also dating at the time). The pair kept their romance very low profile, arriving to award shows and events separately. They dated for two years before calling it quits, and while Ryder and Damon acknowledge their past romance, they refuse to discuss it.
Did You Know? Despite attempting to keep their relationship out of the public eye, the two were declared "Hollywood's It Couple" by People Magazine in 1999.
Kim Kardashian & Nick Lachey
An arguably random and strange romance, reality star and media mogul Kim Kardashian briefly dated 98 Degrees member Nick Lachey in 2006, following his split from Jessica Simpson. The "relationship" was so short-lived it only lasted one week. Lachey has since alleged that Kardashian used their brief romance for publicity and fame. He once told The Huffington Post, "Let's just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside. There are certain ways to play this game, and some people play it well."
Did You Know? While it may not have been a match made in Hollywood heaven, both Lachey and Kardashian have found happiness in their love lives. Lachey is married to Vanessa Minnillo and Kardashian to rapper Kanye West.
Mila Kunis & Macaulay Culkin
The actors began their 8-year-romance back in 2002, while Kunis was still starring on That 70's Show and Culkin was at the height of his fame due to successful films including Uncle Buck (1989) and the Home Alone (1990) series. The duo kept their relationship private, and ultimately ended things in 2011. In an interview with Howard Stern, the actress expressed, "He was huge. You couldn't walk down the street with him. He always had this weird attraction, like fans just screamed when they saw him...Fans responded in a very abnormal way to him."
Did You Know? Kunis is now married to fellow-actor Ashton Kutcher, whom she starred with on That 70's Show. Kutcher even gave Kunis her first kiss on the set of the show!
Drew Barrymore & Tom Green
Back in 2001, the wild and outrageous MTV talk show host Tom Green shocked everyone when he married Hollywood sweetheart Drew Barrymore. The duo had appeared together in the 2000 blockbuster Charlie's Angels. Unfortunately, the marriage between the Canadian comedian and actress only lasted nine months. Green has since called the short-lived relationship a "crazy, whirlwind of a time." He would also say, "I haven't talked to her in many, many years. I'm glad she's doing great. I'm really happy she's doing good."
Did You Know? In 2001, the then-couple escaped uninjured when a fire badly damaged Barrymore's home. The pair were able to escape with the aid of their dog, who woke them up and alerted them to the fire.
Emily Blunt & Michael Buble
Actress Emily Blunt and crooner Michael Buble dated for three years between 2005 and 2008. Cheating claims circulated, alleging that Buble had been unfaithful to Blunt. The "Haven't Met You Yet" singer has repeatedly denied such allegations. Looking back, Buble mused, "It ended because we weren't right for each other, and we are now exactly where we're supposed to be in our lives." Emily Blunt is now married to fellow actor John Krasinski and Michael Buble is married to Argentine actress Luisana Lopilato.
Did You Know? Buble wrote the lyrics of his song "Everything" for Emily Blunt.
Ryan Reynolds & Alanis Morissette
While Ryan Reynolds and Alanis Morissette might be happily married to other people--actress Blake Lively and hip hop's Souleye, respectively--there once was a time when the Canadian transplants were set to exchange nuptials. The unlikely pair met in 2002 at a birthday party for Drew Barrymore, and would go on to date for two years before becoming engaged. Though they never set a date, Morissette had told People magazine in 2005, "We feel like we're already married." They ultimately ended their romance in 2007.
Did You Know? Morissette has stated that her album Flavors of Entanglement was created out of her grief over her break-up with Reynolds, saying that "it was cathartic."
Sarah Jessica Parker & Robert Downey Jr.
Sex and the City star and style icon Sarah Jessica Parker had a significant relationship with Iron Man and Avengers movie star Robert Downey Jr. The pair were together from 1984 to 1991, during a time Downey Jr. was struggling with addiction, a fact that contributed to their split. In an interview with Howard Stern, Downey Jr. reflected on the often rocky relationship, saying, "We were at a very conservative relationship concerning the fact that she was normal and I was out of my mind. I did the best I could." Both actors went on to find love, Downey Jr. with producer Susan Levin and Parker with fellow actor Matthew Broderick.
Did You Know? The pair first met on the set of the 1984 film, Firstborn where they had minor supporting roles.
Lindsay Lohan & Wilmer Valderrama
Back in 2004, Lindsay Lohan was riding high on the success of Mean Girls, while Wilmer Valderrama was making America laugh on That 70's Show. They came out as a couple after Lohan turned 18 (Valderrama was 24). It was during this time that the teen idol was experiencing emotional and physical issues. In October of that year, she was hospitalized for exhaustion and Valderrama stuck by her side. However, less than a year into the relationship the two called it quits.
Did You Know? Lohan's single "Over" from her album Speak was written about Valderrama. She confessed on Ellen that she wrote it the day after their split, while they were still living together.
Blake Lively & Leonardo DiCaprio
Leonardo DiCaprio is known for wooing many beauties, and the Hollywood hunk had a brief romance with the lovely Blake Lively in 2011. The actors enjoyed a whirlwind romance filled with glamorous trips to exotic locations across the world. They were spotted on intimate dates in Disneyland, Venice, Monte Carlo and Saint-Paul de Vence in France. While the two attempted to keep their relationship low-profile, news outlets were heavily invested in the pair. However, after 5 months the romance fizzled out. Blake Lively is now married to Ryan Reynolds and DiCaprio is currently dating Camila Morrone.
Did You Know? The actors met when Lively auditioned for Daisy Buchanan in The Great Gatsby, a film that starred Leonardo DiCaprio. She lost out to the British actress Carey Mulligan.
Sandra Bullock & Ryan Gosling
Back in 2002, actors Sandra Bullock and Ryan Gosling fell in love on the set of their thriller film Murder By Numbers. Bullock played a cop chasing a young rich kid (Gosling) who she suspected had murdered a young girl. Despite a 16-year age difference, the pair dated for over a year, until distance led them to call it quits. Their split was amicable and ultimately for the best, as Gosling found love with actress Eva Mendes and Bullock is currently dating photographer Bryan Randall.
Did You Know? Actor Hugh Grant had teased his friend (Bullock) over her relationship with the younger man. He had told reporters, "I'd do the sound of a baby crying, and she'd know who I meant."
Justin Timberlake & Fergie
Pop superstar Justin Timberlake and singer/former Black Eyed Peas member Fergie had a brief fling back in 1996, when Timberlake was 16 and Fergie was 23. The odd coupling was before he skyrocketed to fame with *NYSYNC and publicly began dating pop princess Britney Spears. Fergie had been 1/3 the girl group Wild Orchid at the time. Their short-lived romance didn't last long. In an interview with Cosmopolitan, Fergie had revealed, "Justin and I would go out together and have fun and make out. But we were never serious. He was Mr. Right Now."
Did You Know? Timberlake joined Fergie and The Black Eyed Peas on their 2003 his song, "Where Is the Love?".
Tyra Banks & Seal
Before his high-profile relationship with another Victoria's Secret angel, musician Seal had romanced supermodel Tyra Banks, who was 11 years his junior. They dated back in 1996, and for the most part kept their romance under the radar. They went out as a couple only a few times, one of the more publicized times being to the Essence Awards. Their relationship was short lived, having ended in the fall of 1996. Seal would go on to marry fellow Victoria's Secret model Heidi Klum, whom he was married to for 9 years.
Did You Know? Seal apparently has a things for supermodels! He has dated German model Tatjana Patitz, Tyra Banks, and Heidi Klum.
Danielle Fishel & Lance Bass
Boy Meets World star Danielle Fishel and former *NYSNC member Lance Bass attended her high school prom together; the couple were dating at the time. The actress dated the boy bander from 1999 to 2000 (Bass would later publicly come out as gay in 2006). Fishel wrote about her relationship with the singer in her memoir, where she revealed that Bass broke up with her a month after prom. She had revealed Lance said, "If I can't make things work out with Danielle, who is beautiful and wonderful, then I must be gay." The two remain close friends.
Did You Know? Fishel has gone on to find love with Jensen Karp, whom she married in 2018. Bass has been married to Michael Turchin since 2014.
Demi Moore & John Stamos
Back in the early 1980s, John Stamos had a very short lived romance with fellow General Hospital soap star Demi Moore. They had appeared on the show together in 1982, and had a brief fling. During an appearance on The Howard Stern Show, John Stamos candidly admitted he couldn't remember having sex with the actress, but that she was a beautiful girl. Moore has yet to confirm any relationship she had with Stamos.
Did You Know? Demi Moore and John Stamos aren't the only famous faces to appear on General Hospital; Elizabeth Taylor, Mark Hamill, Ricky Martin and Rick Springfield have all guest-starred on the soap opera.
© 2018 Rachel M Johnson