An Ode to the Love Story of Ashlee Simpson and Pete Wentz

Oh to be young, emo, and in love in 2007!
June 21, 2017, 3:48pm
Jesse Grant / Stringer

This Week in 2007 is a weekly column looking back on Lindsay Lohan, the first iPhone, George W. Bush, and everything else we loved about the year 2007.

Pete Wentz, bassist for pop-punk band Fall Out Boy, was celebrating his 27th birthday at his own nightclub, Angels and Kings, in Brooklyn when reporters spotted him hobnobbing in the bathroom with fellow pop-punk musician Ashlee Simpson. (She was more pop than punk, but if the bangs swooped and the lyrics were confessional in the emo era, you were punk.) Pete responded, "Not cocaine!" when New York Magazine questioned their toilet activities. "Which the British press would love to accuse me of. I walked her in there. She peed, and then I peed."

It was the summer of 2007, and it was a prime time to be young, emo, and in love. Vanity Fair's Nancy Jo Sales had dubbed Ashlee "sister ilk" to Britney Spears, Paris Hilton, Lindsay Lohan, and Nicole Richie, and Pete was the closest thing to A-list in what Jo Sales called "Lords of the Fly." (That is, the K-Fed's and Cisco Adler's that achieved fame through fucking the girls that US Weekly chronicled like heroines in serialized Charles Dickens novels.) Sure, Pete was boosting his Q-score by dating a gossip starlet, but he could still play the bass and write those damn, catchy Fall Out Boy songs. He was Beethoven compared to Brandon "[Lindsay Lohan is a] firecrotch!" Davis.

Tabloid coverage about the guys and dolls of Young Hollywood could get sexist and nasty, but the early days of Pete and Ashlee's love story were innocent and somber, the calm before Lindsay Lohan's career and the global economy simultaneously blew up.

Read more: How 2007 Became a Meme

Their romance began, like many events in the cultural memory of 2007, in 2006 at the MTV Video Music Awards, where journalists captured them leaving together. A few months later, they entered a Grammys party arm-in-arm, and vacationed in March in Cabo San Lucas, where Ashlee donned Pete's trademark fedora.

I'm attracted to creative people and train wrecks, and there's no shortage of that in Los Angeles.

He told Rolling Stone of Ashlee that same month, "Maybe in a different universe, we'd be some hot couple, but not in this one." Pete clarified, "I'm attracted to creative people and train wrecks, and there's no shortage of that in Los Angeles."

The next month, Ashlee attended the opening of Angels and Kings. Bright Lights, Big City author Jay McInerney said, "Ashley [sic] Simpson was pouting in a corner" in House & Garden magazine. (Culture was so low in the mid-2000s even Jay covered emo love affairs!)

Rumors grew, and by June 2007, they had stopped denying their relationship. Confirmation stirred sexist rumors that Pete penned songs for Ashlee after she told Cosmopolitan about her new Tori Amos-inspired direction. "I love Warhol, of course," Ashlee explained to MTV News. "Pop Art is always a good thing." Pete defended his damsel to the cable TV channel on June 5 2007: "That's pretty much the silliest rumor I've ever heard." It was a gross, misogynistic tabloid tale, but a Disney movie compared to gossip mill stories about actual Disney star Lindsay Lohan.

Pete and Ashley danced it off, partying in the red rooms at Angels and Kings, the Max's Kansas City of mid-2000s emo, for Pete's birthday. Ashlee gifted him a Revenge of the Jedi poster (the original title for Episode VI) and a man bag. "I'm just her purse," Pete told New York. "Look, I have her credit card!"

A few months later, they threw a 1980s prom-themed rager for Ashlee's 23rd, where she wore a pink dress and crown and he slicked his emo bangs back and rocked a white suit. They posed for high school yearbook pictures and kissed for photos that will live on as Getty Images till the end of time.

As Modest Mouse once pointed out, though, the good times can kill you. (And the good press always ends.) In September 2007, the couple vacationed in Vegas with Ashlee's dadager, Joe Simpson, and the Gym Class Heroes. Jet nightclub's bouncer refused to let the band into the venue, and Pete demanded that they be let in. "What are you doing?" he shouted at the security guard according to the New York Daily News: "This is my [bleeping] car! I paid for this [bleeping] car!" Joe joined in, telling the tabloid, "When somebody messes with my baby, then it's over!"

The family that yells at bodyguards together sticks together in the public's mind, at least until rumors spread that the son likes to kiss boys. In December 2007, it was rumored that Joe had turned on Pete and banned him for Christmas because the pop-punk star told Blender magazine that he liked to "kiss" other men. Wentz denied these accusations to MTV News, "I think Joe gets a really bad rap in the press. He's always been nothing but nice to me," while Ashlee assured the same outlet, "I'm going home to be with the family for Christmas. And YES Pete is coming and YES my dad is happy to have him."

Mid-2000s sexism didn't let their nice relationship rest. That same month, fans accused Ashlee of preventing Fall Out Boy from scoring Grammy nominations. "We don't blame a certain someone [Ashlee] for our lack of a Grammy nod," defended guitarist Joe Trohman on his blog. "Don't believe the gossip columns out there. This 'poisonous' person that was mentioned is nothing short of awesome, and we fully back her." The Guardian even felt obligated to write the headline, "Ashlee Simpson Is No Ono." In response to fans calling him "Sell Out Boy," Pete told Vanity Fair, "They keep telling me I'm a mogul!"

But it was ultimately peaceful in comparison to the 5150 holds and rehab visits that defined the winter of 2007 and early 2008. Pete and Ashlee got into minor club spats, denied tabloid reports, and fought sexist rumors, but the two loved each other. They posed for frickin' high school yearbook photos. In a celebrity era of mental breakdowns and DUIs, Pete and Ashlee were more the Sonny and Cher than the Sid and Nancy of the mid-2000s. And they'll always be remembered as a bright spot in low culture.