In an interview with TooFab, the 36-year-old singer-songwriter revealed that Ross, 30, sought his approval before asking out Simpson, 34. The “True” singer admitted to knowing the Ashlee + Evan stars “were talking” before his pal Ross “came over” to express his interest in dating his ex of 15 years.
“I happened to be asleep at the time,” Cabrera recalled during the Friday, July 5, interview. “He specifically came to my house to come have a chat and be like, ‘Yo, I wanted to see what you thought about it. Is everything good?’ He knew that I’d be, like, ‘Oh! All right, cool.’”
Cabrera then shared how he learned of his friends dating from TMZ, which led him to call Ross to ask whether the pair “were together.” When Ross confirmed the news, Cabrera recalled him saying: “Yes, that’s why I came over the other night.” Despite this, the “Shine On” singer confirmed that he is “great friends” with his former flame, noting how it “ruled” that Simpson and Ross found happiness together.
“She ended up marrying one of my best friends,” Cabrera told the website. “How it all happened? Who knows. … L.A. and us all as artists and singers and actors and entertainers essentially, it’s a very small family. Obviously, everybody knows everybody, for the most part. And me and Ashlee were always really, really close. Like, our breakup was pretty … pretty, pretty smooth — other than a couple of things. But we remained friends, like, very shortly after we broke up, and then remained friends from that point on. And we were always cool.”
The “On the Way Down” singer then touched on his long friendship with Ross, explaining how he has been friends with the Hunger Games actor for 15 years and that “he used to sleep on my couch when he was 18 years old.” However, Cabrera noted that, in time, the actor and his former girlfriend would later discover their mutual attraction for each other.
“Eventually, obviously, there was something there with them. I think 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,” Cabrera continued. “People always think it’s weird. 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.”
The reality star, who split with Cabrera in 2004, began dating Ross in 2013. The couple then tied the knot in a star-studded affair held in Greenwich, Connecticut, in August 2014.
Simpson and Ross are parents of 3-year-old daughter Jagger, and the “Autobiography” singer also shares 10-year-old son Bronx with her ex-husband, Pete Wentz. The “Piece of Me” artist was married to the Fall Out Boy bassist, 40, from 2008 to 2011.
In December 2018, the longtime loves shared their admiration for Wentz in an exclusive interview with Us Weekly. “He’s amazing. Yeah, we’re all close friends. Thank God,” Ross noted to Us at the time, to which Simpson added, “Seriously. We really lucked out.”