Superstar couple Ashlee Simpson and Evan Ross have been together for years. The two from famous families had their careers and other relationships before hooking up, marrying, and welcoming two children into their family.
Ahead of their 10th wedding anniversary on August 30, 2024, Ashlee Simpson shared with People that the secret to her long-lasting marriage with Evan Ross is growing together. She emphasized that staying connected and evolving as a couple has been key to their strong relationship.
Evan Ross, Ashlee Simpson, and their daughter Jagger Snow Ross at the premiere of ‘L.O.L Surprise!’ at Hollywood Forever on October 6, 2021, in Hollywood, California (Credit: MEGA / WENN)
With a relationship just as strong now as it was in the beginning, let’s take a look at how they started and where they are today:
Ashlee Simpson: From Reality TV to Music Stardom
Ashlee Simpson gained notoriety in the early 2000s simply by association. Simpson’s older sister, Jessica Simpson, was one of the biggest pop stars in America. Still, she quickly ushered herself out from under her sister’s shadow and began her career in entertainment.
Starting with an acting career, Simpson appeared in episodes of the popular show 7th Heaven as a teenager and occasionally appeared in her sister’s reality show with ex-husband Nick Lachey, Newlyweds: Nick and Jessica.
Ashlee Simpson is the younger sister of Jessica Simpson and was born in Waco, Texas, on October 3, 1984 (Credit: LK / WENN)
Simpson eventually scored her reality television show, The Ashlee Simpson Show, which chronicled her life as she wrote and recorded her debut studio album, Autobiography.
Simultaneously, Simpson publicly dated multiple musicians (more on that later), continued her career as a singer and actress, released another album, and moved her career to the stage.
American singer Ashlee Simpson promotes the 2007 song “Outta My Head (Ay Ya Ya)” from her third studio album Bittersweet World on March 3, 2008, at Wal-Mart in Bensalem, Pennsylvania (Credit: Hugh Dillon / WENN)
Simpson appeared on West End and Broadway shows and recorded and released more solo albums. Eventually, she began focusing more on her life as a mother and wife.
Evan Ross: Stepping Out from the Shadows of Music Royalty
Although Evan Ross has had a fruitful career, it hasn’t been as illustrious as his wife’s. Son of Motown legend Diana Ross and half-brother to black-ish star Tracee Ellis Ross, Ross has followed in the footsteps of both relatives, making a go at both an acting and singing career.
Singer Diana Ross with her children Evan Olav Ross, Chudney Ross, and Ross Naess in 2005 (Credit: Billy Kirk / WENN)
Ross has recorded and released his music and has had roles in significant projects like 90210 and the last two installments of The Hunger Games film series.
A Look Back at Their Previous Relationships
Ashlee Simpson and Evan Ross were involved with other people before committing to one another. Since Simpson’s career has been more publicized, her relationship history has been, too.
When Simpson reached her peak popularity in the early 2000s, she was linked to multiple musicians. Simpson had a very public relationship with singer Ryan Cabrera, who appeared on her television show and inspired some songs on her debut album.
Ashlee Simpson and American musician Ryan Cabrera dated from January 2004 to August 2005 (Credit: WENN)
After splitting from Cabrera, Simpson was involved with other celebrities but eventually began dating Fall Out Boy bassist and lyricist Pete Wentz.
Simpson and Wentz were together for years. First sparking rumors of an engagement by wearing a diamond promise ring, Simpson eventually confirmed that she and Wentz were engaged. Later, in 2008, they wed and welcomed a son, Bronx Mowgli Wentz.
With an unusual middle name inspired by the lead character of ‘The Jungle Book,’ Bronx Mowgli Wentz was born on November 20, 2008, when his mother Ashley Nicolle Ross (née Simpson) was 24 years old.
Unfortunately, the couple filed for divorce three years later, citing irreconcilable differences.
Pete Wentz, Ashlee Simpson, and their son, Bronx Mowgli Wentz, enjoy the day at the park in Los Angeles on July 31, 2010 (Credit: WENN)
As mentioned, Ross’s dating history isn’t quite as well-documented as his wife’s. Still, before his marriage to Simpson, Ross dated model Cora Skinner, Danity Kane singer Aubrey O’Day, and was linked to singer Rita Ora.
The Love Story of Ashlee Simpson and Evan Ross: A Timeline
Ashlee Simpson and Evan Ross have been together since 2013. Here’s a look at their relationship milestones:
1. How Ashlee and Evan First Crossed Paths
Simpson and Ross met at a friend’s birthday party, and the attraction was immediate. The couple engaged physically the night they met before having much of a conversation.
Shortly after, the two began dating and knew they wanted to spend their lives together early in their relationship.
Evan Ross asked ex-boyfriend Ryan Cabrera for permission to date Ashlee Simpson (Credit: FayesVision / WENN)
Beforehand, though, Ross visited his friend, Ryan Cabrera, asking his permission to take Simpson on a date, given their prior relationship. Cabrera, of course, said yes, and Simpson and Ross started their relationship.
2. The Fairy-Tale Proposal and Lavish Wedding
2014 was a big year for Simpson and Ross. Later that year, the two became engaged and married at Ross’s mother’s home in Greenwich, Connecticut.
Ashlee Simpson and Evan Ross married in 2014 after less than a year of dating (Credit: Ryan / WENN)
Simpson’s son, Bronx Mowgli Wentz, walked her down the aisle, and her sister, Jessica Simpson, stood as her maid of honor.
3. Expanding Their Family: Jagger and Ziggy
Not long after tying the knot, Simpson and Ross announced they were expecting a child, and nearly a year after exchanging vows, Simpson gave birth to a daughter, Jagger.
Jagger Snow Ross, Evan Ross, Ashlee Simpson, and Bronx Wentz arrive at the World Premiere Of Disney’s ‘Frozen 2’ held at the Dolby Theatre on November 7, 2019, in Hollywood, Los Angeles (Credit: Avalon / WENN)
A few years later, the duo announced they were expecting another child, and in late 2020, Simpson gave birth to her third child, her second with Ross, a son named Ziggy.
4. Collaborating in Music and TV: Ashlee + Evan
Given that both Simpson and Ross have careers in television and music, it’s natural they would collaborate professionally after a successful romantic relationship. In 2018, the couple debuted several different creative projects.
First, the pair dropped a single they recorded together, “I Do,” and days later, their reality show Ashlee + Evan premiered on E!.
Ashlee Simpson and Evan Ross attend a Spotify event, showing off their chic and coordinated style (Credit: Avalon / WENN)
While the show aired, Simpson and Ross dropped their EP, which had the same title as their television program.
Unfortunately, the show only ran for one season, six episodes total. The two noted they enjoyed filming but had multiple reasons for not wanting to continue. The pair have maintained their musical collaboration, though, releasing another song in 2019.
Fun Facts You Didn’t Know About Ashlee Simpson and Evan Ross
Simpson and Ross are both actors and musicians, but here are other fun facts about the pair:
1. The two are four years apart, and Simpson is older.
2. Ross is much taller than Simpson. He stands at 6’1”, while his wife is 5’7”.
3. Both are active on social media, sharing pictures of each other and their kids on Instagram.
4. The couple enjoys traveling, and both post photos of their trips for fans to see.
Where Are They Now? Inside Ashlee and Evan’s Current Life
These days, Ashlee Simpson and Evan Ross enjoy everyday life in addition to being rich and famous. While they’re not on reality television anymore, both are busy with their families and careers.
Evan Ross and his wife Ashlee Simpson have been dating since 2013 and share a son, Ziggy Blu Ross, and a daughter, Jagger Snow Ross (Credit: Adriana M. Barraza / WENN)
Simpson is also still connected to her ex-husband, Pete Wentz. Although their romantic relationship ended years ago, they are still friendly as they co-parent their son, Bronx Mowgli Wentz.
Both have noted how healthy their relationship is, gushing that Ross, Simpson, Wentz, and their children are all part of a blended family.
As Ashlee Simpson and Evan Ross’s relationship blossomed in the public eye, the pair was frequently spotted enjoying casual outings together. Their undeniable chemistry and love for fashion made them one of Hollywood’s most stylish couples.
A Glimpse into Ashlee and Evan’s Early Days Together
Two days before 2013 ended, Ashlee Simpson was spotted shopping in West Hollywood in Los Angeles.
Ashlee Simpson covers her hair with a fedora on December 29, 2013, in West Hollywood, California (Credit: WENN)
The then-29-year-old singer-songwriter and actress toured Melrose Avenue with her then-25-year-old boyfriend, Evan Ross.
Ashlee Simpson wears a statement necklace and black skinny jeans (Credit: WENN)
Although dressed in just a printed tee and black skinny jeans, the entertainer added some interesting pieces to her laid-back style to keep it interesting.
Ashlee Simpson and her boyfriend Evan Ross on a date in West Hollywood (Credit: WENN)
The younger sister of singer and actress Jessica Simpson added a pop of color to her outfit with a printed cardigan and several long beaded necklaces. She finished her boho-chic look with Ray-Ban sunglasses, a tan hat, and a pair of scalloped-detailed ballerina flats from Chloé.
Ashlee Simpson’s feet in nude Chloé ballerina flats (Credit: WENN)
What do you think of her look? Interesting or too busy? Ashlee was wearing a pair of “Lauren” scalloped flats from Chloé. This style is available in six colors at Farfetch and Nordstrom.