Ashlee Simpson and Pete Wentz were a — temporary — match made in pop rock heaven.

“I’ve always liked guys that have an inner geek. I’m an inner geek myself,” the “Nothing New” songstress gushed after meeting the fellow musician in 2006. “So I don’t like anyone who thinks they’re too cool.”

Two years later, Simpson and Wentz were married with a baby. She was 24 when she gave birth to their son, Bronx, in November 2008.

While fans of the couple may have been shocked when the couple called it quits in 2011, he later shed light on their rocky romance.

“I thought it was a forever thing,” the Fall Out Boy bassist told Howard Stern in 2015. “I’m not the kind of guy … My parents have been married, I think, 35 years. Forty years, this year, maybe? But no, I didn’t [anticipate the split]. At the same time, we were both very young.”

He admitted that after his band went on a lengthy hiatus, their relationship suffered.

“At 31, we’d had all these great years as a band, and then we took time off, and I basically became Mr. Mom. I had the beard, the flannel shirt. I didn’t know what my identity was. That factored in. When your identity is what you do, it’s hard when you stop doing it,” he told Stern. “[I’m thinking], ‘Well, no one’s really taking my picture. I’m just basically hanging out with my kid all day. Who cares?’ think when you stop caring about your personal appearance, your personal hygiene, it makes you even more depressed, but it makes you do it more. It’s like a vicious cycle.”

Things hit the fan when he was “really upset” to be hosting a Jingle Ball event in late 2010. “I wanted to be performing but I wasn’t performing. I drank a bunch of beers and that night, I banged my head and I ended up needing to get stitches,” he recalled. “All this stuff that was not like myself at all, it was part of this cycle of being bummed out.”

At the time, he revealed that it hurt that Simpson left him when he was down.

“I would be an idiot to think that I didn’t contribute to the unraveling of it,” Wentz explained. “Of course, at first, I’m like, ‘This sucks! You bailed on me!’ That kind of stuff. But you get perspective. We have a kid together. Our kid is awesome.”

Both Wentz and Simpson moved on with new partners. He started dating Meagan Camper and the twosome have gone on to welcome son Saint, born in 2014, and daughter Marvel, born in 2018. The Ashlee Simpson Show alum, for her part, wed Evan Ross in 2014, giving birth to daughter Jagger in 2015 and son Ziggy in 2020.

“It could go all different ways. I think the fact that there is a lot of respect amongst all of us. That makes it easier. And we’re all really close friends. It’s easy, we got really lucky with that,” the 7th Heaven alum exclusively told Us Weekly in September 2018.

Scroll through for Simpson and Wentz’s timeline: