The pair even dated one-time fellow best friends and roommates,Gwyneth Paltrowand Winona Ryder (viaCheat Sheet).
“I just heard you guys.
I was sitting here waiting to come on TV,” Damon confessed.

“This is the first time I’ve heard about it.”
At first, Damon was cagey, not wanting to open up about his friend’s love life.
But eventually, Damon’s support of his best friend’s romance shined through the veneer.

I love them both.
I hope it’s true.
That would be awesome."