#15: Adam Duritz: The Beginning

Her age: 26

Duration of Relationship: 1995

In 1995, Jennifer Aniston and Counting Crows frontman Adam Duritz began a brief relationship after meeting at the iconic Viper Room. Their romance sparked from a playful set up by mutual friends, who told each of them that the other had a crush.

This led to an initial curiosity and excitement between the two, even though Duritz admitted he had no idea who Aniston was then. Which, let’s be honest, wouldn’t be possible today due to her immense fame.