14 Of The Weirdest Celebrity Couples Of All Time

The 15 strangest celebrity couples of all time: Frank Otto and Nathalie Volk, Cher Tom Cruise

"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.

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.

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.

Vito Schnabel and Heidi Klum

Heidi Klum separated from her husband Seal in 2012, with whom she seemed perfect on the outside. Then in 2014 she began a relationship with art dealer Vito Schnabel, 13 years younger. However, in 2017 they separated again.

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.

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.

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.

Flavor Flav

This couple knew their relationship might seem strange to outsiders: From 2004 to 2005, Public Enemy rapper Flavor Flav and actress Brigitte Nielsen had a wild romance that was documented in their reality show 'Strange Love.'

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.

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.