If you recall, Ryan and Ashlee dated during pop music's glory days (the mid-2000s) after filming his music video for "On the Way Down" together. The breakup, according to Ryan, was so amicable that the two became close friends "very shortly after."
"We were always cool," Ryan told us. "And then Evan -- he used to sleep on my couch when he was 18 years old. We've been friends for like 15 years."
"Eventually, obviously, there was something there with [Ashlee and Evan]," he continued. "We used to record in this one studio, which we called the fireplace, and I think they met at the fireplace and then kind of hit it off from there."
Jessica Simpson's sister and Diana Ross' son went public with their relationship in July of 2013, two years after Simpson's divorce from Fall Out Boy frontman Pete Wentz. Ashlee and Evan got engaged in January of the following year, and by September, they were married.
But before news broke that the musicians were even dating, Ryan says Evan tried to ask him for his blessing.
"He actually came to my house to kinda like -- I knew that they were talking, we all knew," Ryan explained. "And he came over. I happened to be asleep at the time, but he specifically came to my house to have a chat and be like, 'Yo, I wanted to see what you thought about it. Is everything good?' He knew that I would be like, 'Oh! Alright, cool!'"
But because he was asleep, Ryan never got a formal heads up.
"I think I learned actually through TMZ or something," he said, noting he called Evan immediately. "I was like, 'Ev! Are you and Ashlee together?!' He was like, 'Yeah, that's why I came over the other night!' I was like, 'Ah, that makes total sense. I gotcha. Okay, cool.'"
"People always think it's weird," Ryan said of the love triangle. "I'm like, 'It's not weird! We dated 15 years ago.' I want her to be happy, and I want him to be happy. And it's like, what better way to have two people that you love and actually care about be together and be happy? To me, that rules. I think it's completely normal."
"I think a lot of people probably see a breakup as like it has to be a bad thing, but it's like, at some point, you had love for that person, and it doesn't change just because you're not together," he added. "Just because we didn't work out doesn't mean I want you to do terrible and cry! I want you to be happy. Everyone deserves to be happy. I think it's a beautiful thing. I love Evan, and I love Ashlee, and now we all get to hang out. So it's great."