Adam Duritz's relationship with Courteney Cox was "really hard" because they "just weren't on the same wavelength".

The Counting Crows star, 61, dated the actress in the mid-1990s after previously being set up with her Friends co-star Jennifer Aniston and he's now admitted his romance with Courteney was his "longest" relationship but it didn't work out because they were too "different".

Speaking in the band's new documentary Counting Crows: Have You Seen Me Lately?, Duritz explained: "Courteney was probably my longest relationship, but I don't know whether we were really together for a lot of it.

"We were very, very different people. And there were moments that were absolutely wonderful together and there were moments where it was really hard. We just weren't on the same wavelength."

Duritz's friend Randall Slavin added: "I don't think their relationship was the healthiest thing in the world because Adam wasn't the healthiest thing in the world at that point."

The singer's relationship with Courteney started a year after he'd previously been set up with her Friends co-star Jennifer and Duritz admitted his pals tricked him into going on a date with her but he thought she was "funny", "smart" and "beautiful".

In the film, he explained: "When I met Jennifer Aniston, my friends lied to me and her friends lied to her. They told us we both were really into each other ...

"[I didn't know] anything [about her because I was] busy during prime time ...

"When we were getting ready to record, we would do these shows at the Viper Room [venue in Los Angeles] and we would test out the material, and Jen came to the show and she's cool. She's smart, she's really funny, she's beautiful and she likes me, apparently."

Duritz also dated actress Mary-Louise Parker back in the 1990s and they went on to become longtime friends, but speaking in the documentary she admitted she didn't like some of his other girlfriends.

She explained: "My memories of Adam are 98 per cent platonic. Maybe 98.6. He could have done without a few of those girlfriends, I think. I could have shaved a few of those off the list, very happily."