20+ Celebs Who Fell in Love With Each Other but It Wasn’t Meant to Be

Hollywood is not that big if we take a close enough look inside. Many celebrities know ex-partners of ex-partners, but this is valid for any industry. Back in the ’90s — 2000s, there were a lot of hot couples that attracted media attention, like bees to a honeypot. Luckily, most of them have found their significant other and live true love stories that make us say “Awww” from time to time.

Bright Side wanted to be a little bit melancholic and went back in time to list these 13 famous romances for you.

1. Ryan Reynolds and Alanis Morissette

At the beginning of the 2000s, actor Ryan Reynolds and singer Alanis Morissette were one of the A-list couples of Hollywood. The 2 dated for 5 years, from 2002 to 2007, and they were actually engaged to be married. Shortly after the split, Ryan met actress Scarlett Johansson, but since 2011 the woman who stole the Deadpool actor’s heart is Blake Lively. The 2 have 3 daughters together.

2. Penélope Cruz and Matthew McConaughey

The 2 actors, Penélope Cruz and Matthew McConaughey, only dated for a year, from 2005 to 2006. The Dallas Buyers Club actor even mentions the Spanish actress in Neil Daniels’ 2014 book, Matthew McConaughey: The Biography. Soon after, Matthew laid eyes on his now-wife, Camila Alves. Since 2010, Penelope has been married to actor Javier Bardem and they have 2 children together.

3. Sarah Jessica Parker and Robert Downey Jr.

They met in 1984 on the set of the movie Firstborn, and they were together for 7 straight years, in a time when everybody had their eyes on Hollywood couples. The couple split in 1991, and the star from Sex and The City remembers that this relationship “taught her how to love.” In 1997, Sarah Jessica Parker married Matthew Broderick, and they’ve been together ever since.

4. Mila Kunis and Macaulay Culkin

These 2 had quite a long relationship from 2002 until the beginning of 2011. In 2012, Mila started dating her former colleague from That ’70s Show, Ashton Kutcher. The couple got engaged in 2014 and then married in 2015. The pair has 2 children together: a daughter, Wyatt, and a son Dimitri.

5. George Clooney and Renée Zellweger

George and Renée dated a bit, as the actor from Ocean’s Eleven revealed. Although it was not a very long relationship, the 2 have remained friends for over a decade. In April 2014, George Clooney got engaged to his now-wife Amal, and these 2 never shy away from showing their feelings to each other. The couple welcomed twins in 2017.

6. Katy Perry and Russell Brand

They met in 2009, and they tied the knot in 2010. But after only 10 months, the couple split. Russell Brand was the one who told Katy Perry of his decision via text message, as the singer said in an interview. Now she is engaged to actor Orlando Bloom and the couple welcomed a baby girl in August 2020.

7. Jennifer Lopez and P Diddy

We all remember Jennifer Lopez’s Versace dress from the 2000 Grammy Awards. Back then, she was dating rapper P Diddy (known as Puff Daddy at that time). Their relationship lasted from 1999 to 2001, they actually reunited in 2020 for a live session on Instagram. JLo is now engaged to baseball star Alex Rodriguez. Although there were breakup rumors, they announced they’re still together.

8. Cindy Crawford and Richard Gere

They were a Hollywood “it” couple in the early 1990s. Cindy Crawford and Richard Gere were married from 1991 to 1995. Even the age gap (17 years) didn’t matter when they met in 1988, and the couple had quite an unconventional wedding: in Las Vegas, at a chapel. Her next wedding was in the Bahamas, in 1998, to Rande Gerber. The couple is going strong even today and they have 2 kids together.

9. Gwyneth Paltrow and Brad Pitt

One of Brad Pitt’s most famous relationships from the ’90s was with actress Gwyneth Paltrow. They started dating in 1994 and called it quits in 1997. In 2014, Paltrow met her now-husband, Brad Falchuk on the set of Glee, and they tied the knot in 2018.

10. Julia Roberts and Kiefer Sutherland

They fell madly in love when they met in 1990, but one year later, when the wedding was supposed to happen, they broke up just 3 days before. In 2000, the Pretty Woman actress met Daniel Moder on the set of her film The Mexican. The 2 married in July 2002 and they have 3 children together: twins and a son.

11. Jake Gyllenhaal and Kirsten Dunst

These 2 dated for 2 years, from 2002 to 2004, after being introduced by Jake’s sister. Kirsten Dunst met her now-husband, actor Jesse Plemons, in 2016. The couple welcomed a son in 2018, and now the actress is pregnant again.

12. Katie Holmes and Chris Klein

Katie Holmes met Chris Klein in 2000. The 2 were actually engaged from 2003 and 2005. Katie Holmes later married Tom Cruise. The American Pie actor later wed Laina Rose Thyfault, in August 2015. The couple shares 2 children.

13. Salma Hayek and Edward Norton

They met in 1999 and the 2 dated for 4 years. Although their relationship was highly public, Salma Hayek revealed in an interview that not much was known about them. In 2006, in Venice, the actress met businessman François-Henri Pinault, who later would become her husband. They have been married since 2009 and they have a daughter together.

Which of these couples brings back memories for you? Why were you a fan of these ’90s and 2000s romances?