It's tough living in the towering shadow of a successful sibling or parent, which is a reality that Ashlee Simpson and Evan Ross both know all too well.
Singer Ashlee Simpson grew up alongside actress, singer, and '00s icon Jessica Simpson, while her current husband Evan Ross is the son of The Supremes legend, Diana Ross.
But what brought these two crazy kids together? It's been a long and bumpy road.
Image: Getty.
Ashlee first rose to fame as Jessica's younger sister on Newlyweds: Nick and Jessica, an iconic '00s reality show on MTV that documented the ill-fated marriage of Jessica and Nick Lachey. This cameo ended up securing Ashlee her own reality spin-off show, The Ashlee Simpson Show, which coincided with her first breakout single 'Pieces of Me' in 2004.
The single was a global smash. Ashlee became a superstar. This was a time when emo fashion was soaring, and somehow Ashlee (the brunette aka emo Simpson) became a poster child for alternative pop.
The song 'Pieces of Me' was also sung on Saturday Night Live in a performance that was mocked and parodied for proving that Ashlee allegedly lip-synced her songs, but let's relive that trauma another time, shall we?
Nah, I'm a sucker for punishment, watch the moment right now! Post continues after video.
Simpson's reality show notably featured her appearing in the music video of Ryan Cabrera's 'On The Way Down'. Ashlee and Ryan ended up dating, and he reportedly inspired several songs off her debut album, Autobiography.
But alas, they only dated for about a year as the love story that dominated Ashlee's early years was her tumultuous marriage to Fall Out Boy bassist, Pete Wentz.
The couple started dating after meeting at the MTV VMAs in 2006 aka how all good love stories began in the '00s. By 2008 the pair were engaged, and they were married a month later in an Alice in Wonderland-themed ceremony because let's be real: we're talking about two emos in their 20s.
This couple moved fast as in the same year, Ashlee gave birth to their first son, Bronx.
Image: Getty.
In 2011, Simpson filed for divorce citing irreconcilable differences. “After careful consideration, we have made the difficult decision to file for divorce,” they said via a joint statement at the time.
“We remain friends and deeply committed and loving parents to our son Bronx, whose happiness and well-being remains our no. 1 priority. We ask that everyone honour our privacy as we navigate this next phase of our lives.”
Pete started dating model Meagan Camper in 2011 and they now share two children together, Saint Lazslo and Marvel Jane. Yes, those are their real names.
In a 2015 interview with Howard Stern, Wentz opened up about the reason he cited for their marriage breaking down. "We'd had all these great years as a band, and then we took time off, and I basically became Mr. Mom. I had the beard, the flannel shirt. I didn't know what my identity was," he said.
"That factored in. When your identity is what you do, it's hard when you stop doing it."
Quick! Listen to this episode of The Spill about Kourtney Kardashian's painfully awkward Australian interview. Post continues after podcast.
This brings us back to Ashlee Simpson and Evan Ross. For those unfamiliar with Evan, along with being the son of one of the greatest divas to ever exist (Diana Ross), he's starred in a bunch of movies, but most notably The Hunger Games: Mockingjay.
Ashlee and Evan met during a chance encounter in 2013. “We met at my friend’s birthday party,” Simpson later revealed. “Evan walked in and he was really cute, and I was like, ‘Who’s this Mr. Cool Pants?'”
Ashlee waited for Evan to approach her but when he didn't, she tried to entice him with her dance moves. “You tried to dance with me... You were, like, lifting your leg up and stuff, trying to show me that you dance better than me," Ross joked.
They took their relationship public later that year when they were photographed together and they became engaged in 2014.
The love of my life said YES!!!!!! pic.twitter.com/8CI6ovBAA1
— Evan Ross (@realevanross) January 14, 2014
Never a fan of long engagements, Ashlee married Evan seven months later with his mum, Diana, officiating the wedding and doing a surprise performance of 'Endless Love'. By the end of 2014, the newlyweds were expecting their first child with daughter Jagger Snow coming into the world in July, 2015.
Returning to Ashlee's reality TV roots, the couple have since done a docuseries Ashlee + Evan in 2018 on E! and even released a song together titled, 'I Do'. The couple also launched a fashion line named after their daughter the same year.
And the blessings keep coming as in 2020, the couple welcomed their son, Ziggy Blue. Ashlee is currently 38 years old and Evan is 34, and the couple will celebrate nine years of marriage in August.
Ashlee and Evan's love story is a testament to how life can be unexpected and first marriages aren't always the right fit.
Maybe the Alice in Wonderland-inspired wedding should have been a red flag, just a thought!
Image: Getty/Mamamia.
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