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Some relationships just aren’t meant to be, no matter how much we want them to work. We learn and grow from our relationships and hopefully move on and find the right person. Hollywood stars are no different. They sometimes seem to move on so quickly that we didn’t even know they dated.

Bright Side has compiled a list of celebrity couples that almost got away, and we nearly forgot they were ever together. There’s even a bonus feature waiting for you at the end.

1. Angelina Jolie and Billy Bob Thornton

Angelina Jolie was married to actor Billy Bob Thornton. They got married in Vegas after 2 months of dating and adopted a child from Cambodia. They soon separated after 2 years of marriage.

2. Sienna Miller and Jude Law

The couple got engaged on Christmas Day in 2004. But things went south when Jude Law’s infidelity went public. They separated in 2006 but rekindled their relationship in 2009, and it ultimately ended in 2011.

3. Leonardo Dicaprio and Gisele Bündchen

Before Gisele Bündchen married NFL quarterback Tom Brady, she dated Leonardo Dicaprio from 2000 to 2005.

4. Zachary Quinto and Jonathan Groff

Quinto came out as gay, publicly, in 2011. The Star Trek actor and Glee star had a relationship from 2010 to 2013.

5. Cameron Diaz and Justin Timberlake

The actress and singer were together from 2003 to 2007. Cameron Diaz married Good Charlotte band member Benji Madden in 2015. Justin Timberlake married Jessica Biel in 2012.

6. Natalie Portman and Jake Gyllenhaal

They 2 co-starred in the 2009 film, Brothers, and dated briefly in 2006. The actors remain friends.

7. January Jones and Ashton Kutcher

Way before Ashton Kutcher and Mila Kunis got married, he dated January Jones in the late ’90s. They were both models for Abercrombie & Fitch.

8. Brad Pitt and Christina Applegate

These 2 actors had a very brief relationship in 1989. They went on a date to the MTV VMAs, but Christina Applegate actually ditched the Hollywood heartthrob for another man.

9. Michael Sheen and Rachel McAdams

The Notebook actress and the Underworld actor began dating in 2010 but split up in 2013.

10. Edward Norton and Salma Hayek

The actors began dating in 1999 after reportedly being set up by their chiropractor. They ended their relationship in 2003.

11. Cameron Diaz and Alex Rodriguez

These 2 dated for about a year around 2011 but kept their relationship as low-key as possible.

12. Alanis Morissette and Ryan Reynolds

The Deadpool star and the popular musician were inseparable from the moment they met in 2002. They got engaged in 2004 but never made it down the aisle and broke up in 2007. Ryan Reynolds eventually married Blake Lively in 2012.

13. Rosario Dawson and Jay Z

It doesn’t ever feel like there was a time when it wasn’t Bey and Jay. But the “99 Problems” rapper and the Seven Pounds actress were linked together back in 2000.

14. Anne Hathaway and Topher Grace

These 2 starred in the movie Valentine’s Day together but dated way before the movie was made. They were both new to Hollywood and dated from 1999-2001.

15. Tom Cruise and Penélope Cruz

The Mission: Impossible star dated the Vicky Cristina Barcelona actress from 2001 to 2004.

Bonus: Selena Gomez and Justin Bieber, The Weeknd and Selena Gomez, and The Weeknd and Bella Hadid

Justin Bieber and Selena Gomez had a very public relationship. They had an on-again-off-again relationship over the span of 8 years.

The Weeknd and Selena Gomez were first linked back in 2017. Things ended between them later on that year, but Gomez has said they remain friends.

The Weeknd and Bella Hadid began dating in 2015 after the model appeared in his music video. In 2016, they ended their relationship but dated again in 2018. They eventually called it quits in 2019.

Were there any couples you didn’t know about and were surprised by? What other celebrity couples do you remember?

Angelina Jolie’s timeless style, characterized by her preference for nude pumps, pastel clothes, and power dressing, continues to inspire many, demonstrating her understanding of fashion as a form of self-expression.

In a candid revelation, Kate Winslet shared insights into the dynamics of her intimate scenes with Leonardo DiCaprio. Despite their palpable friendship and on-screen chemistry, Winslet found it challenging to film intimate scenes for “Revolutionary Road,” especially in the presence of her then-husband, director Sam Mendes. DiCaprio, on the other hand, saw their bond as a catalyst for delivering emotionally charged performances.

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