Ashlee Simpson Breaks Silence On Body-Shaming Boyfriend From Over A Decade Ago

By Afouda Bamidele on August 22, 2025 at 10:15 AM EDT

Ashlee Simpson at Vanity Fair Oscar Party
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Ashlee Simpson is breaking her silence, revealing the cruel body-shaming insult from an ex-boyfriend that has lingered with her for more than a decade.

Simpson's love life has been constantly in the spotlight, with a string of high-profile romances and even a marriage that gave her her first child. 

Now happily married to Evan Ross since 2014, the couple shares two children, while Ashlee Simpson also raises her eldest from her previous marriage.

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Ashlee Simpson Recalls Ex's Cruel Comment That Inspired Her Early Music

The singer revealed that during one of her early relationships, an ex made a cutting remark about her body that ended up fueling some of her biggest songs.

She shared that the insult," 'You look fat, you need to get on the treadmill!'" became the spark she needed to channel her emotions into music. Instead of letting it break her down, Simpson turned the painful experience into lyrics that connected with millions.

Looking back, she explained that her songwriting in those years was deeply personal. Each track came from real experiences, fresh heartbreaks, and raw emotions that she poured straight into the recording booth.

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She revealed the memory to "Boy Meets World" alums who host "Pod Meets World," where she discussed how her life at the time became the foundation of her first album, "Autobiography." That record arrived in July 2004 and marked a turning point in her career.

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The Actress's Dating History From Ryan Cabrera To Pete Wentz

Ashlee Simpson at the 5th Jam For Janie Grammy Awards Viewing Party
CraSH/imageSPACE / MEGA

Despite it being over two decades now, Simpson did not reveal the name of the ex who allegedly body shamed her. According to Ranker, she has been linked to a long list of well-known names over the years, making it difficult to pin down who delivered the insult.

In the early 2000s, she shared a close bond with singer Ryan Cabrera. Their friendship turned romantic, and while they appeared smitten, their romance lasted only a few months.

Before that, she briefly dated actor Josh Henderson in 2002, and was also spotted out with "Everwood" star Gregory Smith the following year.

Around 2003, whispers tied her to Carson Daly, though neither confirmed the rumors. She was also loosely linked to actor Tyler Hoechlin in 2004, but again, nothing was official.

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Other names on her dating timeline include Wilmer Valderrama, musician Braxton Olita, and actor Vincent Piazza. But her most famous relationship was with "Fall Out Boy's" Pete Wentz. The pair married in 2008, welcomed a son, and later divorced in 2011.

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Simpson's Life As A MotherĀ 

Simpson may have once made headlines for her dating history, but her life now looks very different. The Blast highlighted that the 40-year-old has built a steady home with actor Evan Ross, and the pair now share two children while she also co-parents her eldest son from her previous marriage to Wentz.

By 2022, Simpson and Ross had already marked eight years of marriage and were raising daughter Jagger Snow and son Ziggy Blu.

When asked if they planned to grow their family, Simpson admitted she felt complete with her three children. "I think we are done," she told E! News, while Ross playfully countered, "We'll see."

Simpson explained that while she loved pregnancy and motherhood, she was not ready to commit to having another baby just yet. Ross, however, made it clear he was open to the idea if she ever changed her mind.

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Inside The Songwriter's Co-Parenting With Pete Wentz

Ashlee Simpson at the 30th Annual Race To Erase MS Gala
Xavier Collin/Image Press Agency/MEGA

While discussing whether she would have other children, she noted that the arrival of Ziggy in October 2020 came with some sibling drama. 

Ross recalled on SiriusXM's "The Jess Cagle Show" that Jagger initially did not take the news well when the gender reveal showed she would be getting a baby brother. Still, the frustration quickly faded.

While Simpson and Ross continue to raise their two children together, she also co-parents her eldest son, Bronx, with her ex-husband. Their marriage ended in 2011 after Wentz struggled with depression and admitted he lost focus on his family during a break from his band. 

Despite the painful split, Simpson has praised their co-parenting relationship. In 2018, she told Us Weekly that she "lucked out" with Wentz as a parenting partner. Ross has also spoken highly of the dynamic, sharing that his wife and her ex maintain a strong friendship for the sake of their son.

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Ashlee Simpson And Evan Ross's Love Story

Evan Ross and Ashlee Simpson at the Spotify Best New Artist 2020 Party. 23 Jan 2020
MEGA

The lovebirds first crossed paths at a friend's birthday party, sparking a romance that quickly moved into the spotlight. By July 2013, the pair were seen together often, before making their relationship official on the red carpet. 

PEOPLE noted that just six months after confirming their relationship, the couple revealed their engagement in January 2014. That August, they tied the knot at the Connecticut estate of Ross's mother, legendary singer Diana Ross.

Since their wedding, the couple has built a life rooted in both family and creativity. Beyond parenting, they have also teamed up professionally, recording music and starring in their own docuseries, "Ashlee + Evan," which gave fans a closer look at their relationship and careers.

Ahead of their 10th wedding anniversary in 2024, Simpson reflected on what has kept their marriage strong. "I think the secret is that we have grown together. I think if you can grow together and stick together, that's probably the key to it all," she explained.

In the end, Ashlee Simpson proved that even the harshest words can be turned into success.

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