Ashlee Simpson Ross, a multifaceted artist known for her music, acting, and reality television presence, has navigated her romantic life in the public eye since her rise to fame. Her journey has seen high-profile relationships, a significant first marriage, and a lasting union, all while maintaining a focus on family and career. From her early days as a burgeoning pop star to her current role as a wife and mother, Simpson's love life has evolved, reflecting different stages of her personal and professional growth.
One of Ashlee Simpson's earliest public relationships was with actor Josh Henderson. The couple dated from 2002 to 2004, during a period when Simpson was beginning to establish herself as a solo artist separate from her famous sister, Jessica Simpson. Their romance offered a glimpse into her personal life as she gained increasing media attention, setting the stage for future public relationships.
Following her split from Henderson, Simpson entered into a relationship with singer Ryan Cabrera. Their romance, which lasted from 2004 to 2005, became a central storyline on her hit reality show, The Ashlee Simpson Show. Viewers witnessed the ups and downs of their relationship, including their eventual breakup, which was openly discussed on the program. Despite their separation, the two remained amicable, often speaking fondly of their past connection.
After brief reported dalliances with musician Ricky Fataar in 2005 and Braxton Olita in 2006, Ashlee Simpson began a pivotal relationship with Fall Out Boy bassist Pete Wentz in 2006. Their romance quickly became a fixture in pop culture, embodying the era's pop-punk aesthetic. The couple's public appearances and shared artistic sensibilities made them a beloved duo among fans and the media.
Their relationship progressed rapidly, with the couple announcing their engagement in April 2008. Just a month later, Ashlee Simpson and Pete Wentz exchanged vows in a private ceremony at her parents' home in Encino, California, on May 17, 2008. The wedding was a significant event, blending their respective rock and pop backgrounds into a high-profile union. The couple soon welcomed their son, Bronx Mowgli Wentz, on November 20, 2008, solidifying their family unit.
However, after nearly three years of marriage, Ashlee Simpson filed for divorce from Pete Wentz in February 2011, citing "irreconcilable differences." The news came as a surprise to many fans, as the couple had often presented a united front. Their divorce was finalized in November 2011, and despite the separation, both Simpson and Wentz have consistently maintained an amicable co-parenting relationship for their son, Bronx, often sharing glimpses of their blended family dynamics.
In the period following her divorce, Simpson was briefly linked to actor Vincent Piazza in 2012, though this relationship was not as publicly documented as her previous high-profile romances. This period marked a more private chapter in her dating life as she focused on her son and personal growth away from intense media scrutiny.
A new chapter began for Ashlee Simpson in mid-2013 when she started dating actor and musician Evan Ross, the son of legendary singer Diana Ross. Their relationship quickly blossomed, characterized by a deep connection and shared artistic passions. The couple's romance was often described as soulful and grounded, a contrast to some of her earlier, more frenetic public relationships.
Their engagement was announced in January 2014, and they married later that year on August 30, 2014, at Diana Ross's sprawling estate in Greenwich, Connecticut. The intimate ceremony was a star-studded affair, celebrating their union within a close family circle. Ashlee adopted the surname Ross, signifying her commitment to her new family.
Ashlee and Evan quickly expanded their family, welcoming their daughter, Jagger Snow Ross, on July 30, 2015. Their family grew once more with the arrival of their son, Ziggy Blu Ross, on October 29, 2020. The couple has often shared insights into their family life, including their experiences raising three children—Bronx from Simpson's previous marriage, and Jagger and Ziggy with Ross. They have also collaborated professionally, releasing music together and starring in their reality show, Ashlee + Evan.
Currently, Ashlee Simpson Ross remains happily married to Evan Ross. Their relationship is frequently showcased on social media, where they share moments of family life, musical endeavors, and public appearances. They are often seen supporting each other's careers and celebrating their bond, demonstrating a stable and loving partnership that has endured the pressures of public life. Their journey from early public romances to a strong, family-focused marriage highlights Ashlee Simpson's evolution both personally and romantically.