In the early 2010s, Diggy Simmons’s love life started to attract publicity attention when he began dating Jessica Jarrell.
For a hot minute, it looked like the two were on their way to each having a successful career in the music industry.
And when they were together, it was rumored that they both wanted their love to last forever.
Who is Jessica Jarrell?
But their romance eventually fizzled out, along with Jessica’s growing fame.
Jessica got her start as a child model, appearing in print campaigns for companies like K-mart and Mattel, per Genius.
But it wasn’t until the late 2000s that she got her break as a Pop R&B singer.
She signed with Island Def Jam and started working on her first album when she was 13.
Her debut radio single was called Armageddon.
Jessica’s first concert performance was during Obama’s 2008 White House Easter Egg Roll, but just over a year later, she was performing to thousands of people in sold out arenas.
In 2010, she collaborated on a song called Overboard with Justin Bieber, and all of a sudden, she found herself opening for him on the first leg of his My World 2.0 Tour.
How Did Jessica And Diggy Simmons Meet?
It wasn’t long after this that she met another up-and-coming teen sensation, who was the son of one of the members of the insanely popular hip hop group, Run-DMC.
Diggy was the 4th child of Joseph Simmons, also known as Rev Run.
He began his music career in 2009, too, so he and Jessica were on the same path to fame in their early teens.
It’s unclear when exactly they first met, but since they were both part of the same record label, there’s a big chance that it led to them crossing paths at some point or another.
In fact, Diggy even appeared in the music video for Jessica’s 2010 song, Up And Running.
When Did Diggy And Jessica Start Dating?
But it might not have been until about a year later that they actually started to date.
Jessica was an ambassador for Pastry Shoes around that time, and the fashion company documented her Sweet 16 birthday party which included other teen celebs.
In the video made for the special event, Diggy wasn’t afraid of showing how close he’d become with Jessica by that point, because in his message for her he said: “Happy Birthday Jess, Love You.”
According to The Wiz, the pair first began getting photographed going out together in the spring of 2011.
An Our Music Is Ours video alleged that the couple’s relationship led to a lot of online hate for Jessica from her boyfriend’s fans, supposedly because they were jealous that their teen heartthrob had been snapped up.
But in an interview with Teen Vogue, the singer claimed that she had thick skin and didn’t let things like that get to her.
When asked how she dealt with public criticism, she shared that there’d always be criticism, just like with anything she did in life.
She said: “Whatever it is that you do, there’s always going to be people that want to criticize you.”
Jessica went on to reveal that her parents had taught her that she was not going to please everybody.
And she was okay with that, as long as she was happy and doing what she wanted to do and what she felt was right.
Diggy and Jessica were still together when they turned seventeen.
Diggy Simmons’ Secret Engagement To Jessica Jarrell
And things were reportedly moving super fast in their relationship.
IB Times revealed that according to sources, the young couple spent their 2011-2012 winter festive period together, and something pretty major happened around Christmas.
The insiders alleged that Diggy proposed to his girlfriend and they’d gotten secretly engaged.
But they were still under the age of consent to legally get married.
Diggy allegedly wanted to wait until the following year when they’d both turned 18.
Why Did Diggy Simmons And Jessica Break Up?
However, the flame that burns twice as bright burns half as long.
Who’s Dated Who claimed that the two singers broke up some time around May 2012 after having been together for almost a year.
Online users on Answers alleged that it was Jessica who broke up with Diggy.
But what really happened remains a secret between the two of them.
After their relationship ended, Jessica kind of faded from the spotlight.
Why Jessica Jarrell Left Def Jam
She parted ways with Def Jam before 2012.
A report by BET said that she left to make music on her own terms.
Things went quiet with her for a couple of years, but she came back onto the music scene in 2015 with her album Goldblooded.
She told BET that it was her first album.
She’d dropped an EP before but never an album, so she was really excited – it was everything she’d wanted her album to be.
Jessica confessed: “I had planned on putting an album out when I was [with] Def Jam but I’m really [happy] that I didn’t.”
Jessica Jarrell’s Music and Acting Career
She explained that the way the album sounded was what she’d wanted her first shot to sound like.
When explaining the album’s title in an interview with Billboard, the then 20-year-old singer shared that people say they have to be tough and they have to be ‘cold-blooded’,
Goldblooded was a play on that.
She added that in life, there are always going to be obstacles, but once people see everything they worked so hard for coming together and realize that nothing can stop them, ‘everything feels golden.’
Two years later, Jessica dropped a new single called How Was I under a new label and performed it at different events around the U.S., according to BVI News.
In 2017, she also dabbled in some homemade reality TV by starting a cooking channel on Youtube and sharing her favorite recipes.
Over the next few years, Jessica continued to release a new single every now and then, but none of them made it onto the charts or had much commercial success.
In 2023, she turned her sights to acting and starred in two movies made for the streaming platform, Tubi Originals.
According to IMDB, neither of them were rated highly.
Why Fans Threw Shade At Jessica Jarrell
But why didn’t she ever make it big?
There’s not one clear answer, but the online world is full of opinions about it.
Someone on Lipstick Alley wrote that Jessica reminded them of a mix of Cassie and Zendaya.
They said that she couldn’t really sing but was being pushed because of her looks.
Another user threw shade at the singer by claiming that she was not focused and had no drive.
They alleged that she was in her 20s and still lived with her parents and was content just posting the occasional TikTok or social media post.
A third user defended her by saying that she did have drive and focus, but she just didn’t care to be mainstream.
The Our Music Is Ours video claimed that it was because black women didn’t get a lot of chances to succeed, whereas other pop stars of her generation like Selena Gomez did.
Are Diggy Simmons And Chloe Bailey Together?
And what about Diggy?
How did things turn out for him after he split with Jessica?
His love life has been somewhat of a mystery.
He appears to keep his personal life private and hasn’t confirmed many of his relationships.
But that hasn’t stopped the speculation.
PopSugar reported that he’d been linked to his Grown-ish co-star Chloe Bailey.
The pair played on screen boyfriend and girlfriend in the show which first aired in 2018.
Their TV romance reportedly led to rumors that they were dating on the DL, especially after they were photographed hanging out off the studio lot as well in 2019, per Vulture.
The gossip mill began churning again a year later when Chloe and her sister Halle were asked if they’d ever dated one of their Grown-ish co-stars during an Instagram Live.
When Halle read the question, she quickly pointed to her sister as if she would be able to answer the question.
But Chloe shut it down.
What Diggy Simmons Looks For In A Girlfriend
According to Who’s Dated Who, Diggy supposedly went out with Sydney Utendahl and Young Lyric too, but that hasn’t been confirmed.
In an interview with BET, the singer-turned-actor did open up a little about his dating preferences.
A dealbreaker for him would be someone who wasn’t able to navigate through different spaces.
He shared that he would often find himself in different rooms, traveling a lot, and doing different kinds of work.
So, he wanted to be able to bring his person along with him and know that they would be able to get along with people.
When he was asked if long-lasting love still existed, he said that he thought that it did.
He explained: “I think that if you find the right person and you’re able to focus on them, without having anything come between the two [of you], it’s possible.”
