Celebrity Relationships That Didn’t Work Out Compared to Their Current Ones That Did

It might look like your regular romantic movie, but it turns out it doesn’t have a happy ending.

Jesse

Published in Film & TV
25 Feb 2022

Celebrity Relationships That Didn’t Work Out Compared to Their Current Ones That Did

Celebrities often run in tight circles. Connections of who knows who and mutual friends get tangled easily.

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This includes their dating pool. If you look at it, it’s not as big since many of them date each other, and you’d be surprised by their exes.

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There are stories about how they met, and usually, they revolve around meeting on sets or at events that celebrities attend. However, the hottest era for ‘it’ couples was the 90s and 2000s.

This was the time when the media intently followed the start of relationships and their downfalls. There was significant coverage in tabloids about who’s dating and who’s already moving on.

Surprisingly, most celebrity couples on this list were in long-term relationships and engaged with each other before everything ended. These are also the couples who ended up with other famous people after their last relationships.

Even though celebrities can date whoever they want, they might choose to keep their options within the industry for that sense of normality. They may be able to navigate their public lives better if their partner can relate to them, but unfortunately, even if that’s the case, some relationships aren’t meant to soar, and they find luck in the next one.

1. Long before Ryan Reynolds became the iconic superhero that he is, he dated Alanis Morissette, and they were even engaged for a while before they broke it off.

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2. Penelope Cruz and Matthew McConaughey were a hot item as they dated for a year until things weren’t alright anymore.

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3. A young Robert Downey Jr. and a young Sarah Jessica Parker were together for seven years until they split up in 1991.

4. Mila Kunis and Macaulay Culkin saw each other grow up as they dated for a long time before breaking up and moving on with their new relationships, respectively.

5. Ex-lovers turned friends? That’s what happened to George Clooney and Renée Zellweger after they decided to go their separate ways.

6. One of the most talked-about breakups was Katy Perry’s and Russell Brand’s, as the nature of how it happened was revealed to the public.

7. If you remember Jennifer Lopez during the 2000 Grammy Awards with her famous dress, you might recall who was right there beside her—none other than P Diddy.

8. Want to talk about 90s ‘it’ couples? Cindy Crawford and Richard Gere are sure to be on that list.

9. Brad Pitt had his fair share of famous relationships, and one of them was the fabulous Gwyneth Paltrow.

10. Julia Roberts and Kiefer Sutherland fell into a whirlwind romance that ended three days before their wedding day.

20+ Celebs Who Fell in Love With Each Other but It Wasn’t Meant to Be © ASSOCIATED PRESS/East News, © John Shearer/Invision/AP/East News

11. Thanks to a fortunate introduction, Kirsten Dunst and Jake Gyllenhaal dated for about two years until they called it quits.

12. Another engaged couple that didn’t work out in the end is Katie Holmes and Chris Klein.

13. Salma Hayek and Edward Norton’s relationship was closely followed by the public, but even after they broke up, there was still a lot that happened that people didn’t know.

There might be extra pressure for celebrities when they date each other. It’s double the scrutiny and less privacy.

Seeing all those who dated really shows how small the industry is in terms of their dating pool. There were many surprises, some of which are too iconic not to be known.

Which celebrity exes surprised you the most? You can tell us in the comments.

Celebrity Relationships That Didn’t Work Out Compared to Their Current Ones That Did

Jesse

1. Long before Ryan Reynolds became the iconic superhero that he is, he dated Alanis Morissette, and they were even engaged for a while before they broke it off.

2. Penelope Cruz and Matthew McConaughey were a hot item as they dated for a year until things weren’t alright anymore.

3. A young Robert Downey Jr. and a young Sarah Jessica Parker were together for seven years until they split up in 1991.

4. Mila Kunis and Macaulay Culkin saw each other grow up as they dated for a long time before breaking up and moving on with their new relationships, respectively.

5. Ex-lovers turned friends? That’s what happened to George Clooney and Renée Zellweger after they decided to go their separate ways.

6. One of the most talked-about breakups was Katy Perry’s and Russell Brand’s, as the nature of how it happened was revealed to the public.

7. If you remember Jennifer Lopez during the 2000 Grammy Awards with her famous dress, you might recall who was right there beside her—none other than P Diddy.

8. Want to talk about 90s ‘it’ couples? Cindy Crawford and Richard Gere are sure to be on that list.

9. Brad Pitt had his fair share of famous relationships, and one of them was the fabulous Gwyneth Paltrow.

10. Julia Roberts and Kiefer Sutherland fell into a whirlwind romance that ended three days before their wedding day.

11. Thanks to a fortunate introduction, Kirsten Dunst and Jake Gyllenhaal dated for about two years until they called it quits.

12. Another engaged couple that didn’t work out in the end is Katie Holmes and Chris Klein.

13. Salma Hayek and Edward Norton’s relationship was closely followed by the public, but even after they broke up, there was still a lot that happened that people didn’t know.

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