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  1. Home
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  3. 13 Of The Strangest Celebrity Couples Of All Time

13 Of The Strangest Celebrity Couples Of All Time

Mahima Kharbanda / March 16, 2026 - 06:00 am

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Pinterest Celebrity couple Frank Otto and Nathalie Volk, Cher Tom Cruise
(© Imago Images (ZUMA Wire) / Getty Images)

Strange celebrity couples

"Where love leads" is probably what comes to mind when thinking of these 13 couples, who had some of the most unusual celebrity relationships ever. Unfortunately, only a few of these relationships have stood the test of time.

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Pinterest Cher and Tom Cruise
(© IMAGO / ZUMA Wire)

Cher and Tom Cruise

At the very beginning of his career, Tom Cruise met pop icon Cher. Although she was 16 years older (he was 23, she was 39), a relationship developed between the two. In an interview, Cher even revealed that the
'Mission Impossible' star is one of her top 5 lovers. However, the love lasted only a few months.

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Pinterest Ryan Reynolds and Alanis Morissette in 2004
(© imago / Picturelux)

Ryan Reynolds and Alanis Morissette

Yes, you read that right: Ryan Reynolds and Alanis Morissette used to be a couple. The actor and the singer met at Drew Barrymore's birthday party in 2002. Two years later, they even got engaged! Maybe they were connected by their home country? Both come from Canada. In 2007, however, it was over.

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Pinterest Britney Spears and Colin Farrell
(© Getty Images)

Britney Spears and Colin Farrell

The pop princess Britney Spears and the Irish bad boy Colin Farrell caused a stir in 2003 when they were seen canoodling in clubs and bars. However, it was reportedly not a relationship and quickly ended.

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Pinterest Ashton Kutcher and Demi Moore Apple Awards
(© IMAGO / Picture Perfect)

Ashton Kutcher and Demi Moore

Before Mila Kunis, Ashton Kutcher was in a relationship with Demi Moore for years. Their relationship was unusual, especially at the beginning, as the actress is 16 years older than Kutcher and already had three children when they began dating. Nevertheless, the two were married for eight years.

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Pinterest Evan Rachel Wood Marilyn Manson 2007 couple
(© Getty Images)

Evan Rachel Wood and Marilyn Manson

Evan Rachel Wood was only 18 years old when she entered into a relationship with the then 36-year-old shock rocker Marilyn Manson. Although outwardly the two did not match at all, they got engaged in 2010 after five years of relationship. In the same year, the unequal couple announced their separation.

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Pinterest Heike Makatsch Daniel Craig 2001 Couple
(© imago / Future Image)

Heike Makatsch and Daniel Craig

Looking back today, it seems unusual, but the actress Heike Makatsch and 'James Bond' actor Daniel Craig were actually a couple for eight years! From 1996 to 2004, the German actress was the Bond girl at the side of the then relatively unknown actor.

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Pinterest Macaulay Culkin and Mila Kunis used to be a couple
(© Getty Images)

Macaulay Culkin and Mila Kunis

Mila Kunis and Ashton Kutcher seem like a match made in heaven. However, before the two found each other, the stunning Ukrainian actress was in a relationship with 'Home Alone' star Macaulay Culkin for a whopping nine years, from 2002 to 2011.

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Pinterest Sarah Jessica Parker and Robert Downey Jr. fell in love on set while filming Firstborn at the beginning of the eighties.
(© IMAGO / Everett Collection)

Sarah Jessica Parker and Robert Downey Jr.

The celebrity couple of Robert Downey Jr. and Sarah Jessica Parker was an unlikely pair that lasted for seven years in the 1980s. However, both have since moved on and are happily married to other partners.

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Pinterest Woody Allen Soon-Yi Previn 2003 Couple
(© Getty Images)

Woody Allen and Soon-Yi Previn

Their love story is indeed a bit strange. Soon-Yi Previn was adopted by Mia Farrow, with whom Woody Allen had a relationship for twelve years. The actor and director started an affair with the Korean woman while he was still with Farrow. When this was revealed in 1992, Soon-Yi moved in with Allen. They got married in 1997 and are still happily together to this day, despite the 35-year age difference between them.

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Where love leads is probably what comes to mind when thinking of these 15 couples, who had some of the most unusual celebrity relationships ever. Unfortunately, only a few of these relationships have stood the test of time.

Hardly imaginable today: Tom Cruise and music icon Cher were a couple many years ago. Who else was or still is together, you can see in our gallery. 

The strangest celebrity couples of all time

Did you know that Ryan Reynolds and Alanis Morissette were once a couple? The actor and the singer met at Drew Barrymore's birthday party in 2002 and were engaged two years later. Perhaps their shared Canadian nationality played a role in their connection. However, the relationship ended in 2007.

Mila Kunis and Ashton Kutcher are a perfect match today. However, before they found each other, the stunning Ukrainian was in a nine-year relationship with Macaulay Culkin. Their relationship lasted from 2002 to 2011, but eventually, it came to an end.

Ashton Kutcher was also previously in a relationship with a celebrity woman with a significant age difference - Demi Moore. The actress is a proud 16 years older and already had three children at the time of their relationship. Nevertheless, the two were married for eight years. Do you know of any other strange celebrity couples? No? Then click through our picture gallery.

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