They were the blueprint for the 2008 Tumblr aesthetic. Long before "indie sleaze" was a vintage trend, Ashlee Simpson and Pete Wentz were living it in real-time. He was the eyeliner-clad king of Fall Out Boy, and she was the pop-punk princess who’d survived that infamous SNL lip-sync debacle and emerged with a gritty new sound. When they got together, it felt like the ultimate crossover event for teenagers who spent their weekends at Hot Topic.
But then, it just... ended.
The Alice in Wonderland Wedding That Started It All
Honestly, looking back at their May 2008 wedding feels like a fever dream of mid-2000s celebrity culture. It wasn't some minimalist, "quiet luxury" affair. They went full Alice in Wonderland. We’re talking black roses, red couches, and a Sam Godfrey cake topped with a teapot and a stopwatch. It was held at the Simpson family home in Encino, and yes, Joe Simpson officiated the ceremony.
There’s something so uniquely 2008 about Pete Wentz’s English bulldog, Hemingway, serving as the ring bearer. Ashlee wore an ivory Monique Lhuillier gown and was, as we later found out, already pregnant with their son, Bronx Mowgli. The wedding was a massive deal. 150 guests, including Nicole Richie and Joel Madden, watched them exchange vows in a ceremony that basically cemented them as the reigning royals of the alternative-pop scene.
Why Ashlee Simpson and Pete Wentz Actually Split
When Ashlee filed for divorce in February 2011, people were genuinely shocked. They seemed like a solid unit. But the reality was way messier than the paparazzi photos at In-N-Out suggested. Pete has since been incredibly open about why things fell apart, and it basically boils down to a perfect storm of identity crises and being way too young.
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Fall Out Boy had gone on hiatus in 2009. Pete went from being a global rock star to, in his own words, "Mr. Mom." He grew a beard, wore flannels, and stayed home with Bronx. While that sounds nice in theory, Pete admitted to Howard Stern years later that he felt his identity was disappearing. If he wasn't the guy on stage, who was he?
"When your identity is what you do, it's hard when you stop doing it," Pete explained.
This period led to a deep depression. He stopped caring about his appearance and his hygiene. He felt invisible because nobody was taking his picture anymore. Meanwhile, the couple was "fighting nuclear." They didn't know how to argue without things escalating to a point of no return. Ashlee was 26 and Pete was 31 when they called it quits, citing "irreconcilable differences." It was a classic case of marrying young, having a kid immediately, and realizing you’re two different people once the initial rush wears off.
The "Modern Family" Masterclass
If you’re looking for a celebrity breakup that didn't turn into a decade-long legal war, this is it. They figured out co-parenting better than almost anyone in Hollywood. Pete has gone on record saying that Ashlee and her husband, Evan Ross, are "amazing" co-parents.
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It's actually kind of heartwarming. Evan Ross has even said he and Pete are "homies." They all show up for Bronx, who is now 17 and looks like a literal clone of his dad. Seriously, go look at the photos from Bronx's 16th birthday in late 2024. He’s a head taller than Ashlee and has that same brooding, musician energy Pete had in the "Sugar, We're Goin Down" era.
Ashlee Simpson and Pete Wentz didn't let their split ruin their son's childhood. They share 50/50 custody and stayed communicative even when things were raw. It’s a rare win in a world of messy celebrity disposals.
Life in 2026: Where Are They Now?
Ashlee has mostly stepped away from the music grind. She’s married to Evan Ross—son of the legendary Diana Ross—and they have two more kids together, Jagger Snow and Ziggy Blu. She seems happy being a mom and occasionally popping up for fashion events or a nostalgia-fueled performance in Vegas.
Pete, on the other hand, stayed with Fall Out Boy through their massive second act. He’s been with his longtime partner Meagan Camper since 2011, and they have two children, Saint Laszlo and Marvel Jane. He still tours, but he’s admitted that the "mental part" of leaving his kids to go on the road is much harder now than it was in his 20s.
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What You Can Learn From Their Story
The biggest takeaway from the saga of Ashlee Simpson and Pete Wentz isn't about the drama. It’s about the "after."
- Identity matters: If you tie your entire self-worth to your job, you're going to crash when that job changes. Pete’s struggle with the Fall Out Boy hiatus is a huge warning sign for anyone who doesn't have a life outside of work.
- The "Nuclear" Argument: Learning how to disagree without destroying the relationship is a skill. Pete and Ashlee didn't have it then, but they learned it later.
- Blended families can work: It requires leaving your ego at the door. If Pete and Evan Ross can be "homies" for the sake of Bronx, most people can find a way to be civil.
If you’re going through a life transition or a breakup, take a page out of their book: focus on the people who matter, get professional help for the depression if you need it, and don't be afraid to reinvent yourself when the old version of you doesn't fit anymore.
Check out Pete's 2023 interviews with Apple Music's Zane Lowe for a deeper look at his mental health journey—it's a surprisingly raw look at what happens when the cameras stop flashing.