Even if a celebrity couple doesn’t stay together forever, they can still leave a lasting impression on their fans through their relationships. But in the last few decades, many famous couples who were thought to be inseparable broke up and never had kids together.

1. Jennifer Lopez and Ben Affleck

2. Johnny Depp and Kate Moss

3. Cameron Diaz and Matt Dillon

4. Jake Gyllenhaal and Kirsten Dunst

5. Winona Ryder and Matt Damon

6. Drew Barrymore and Luke Wilson

7. Leonardo DiCaprio and Gisele B√ľndchen

8. Brad Pitt and Gwyneth Paltrow

9. Cindy Crawford and Richard Gere

10. Matthew McConaughey and Sandra Bullock

11. Justin Timberlake and Britney Spears

12. Jessica Biel and Chris Evans