When her dad Rev Run was offered a reality show that featured his family, Angela Simmons got her first taste of fame on the show Run’s House and the spinoff series Daddy’s Girls. While fans were interested in learning more about her business ventures, including her Pastry shoe line she launched with her sister Vanessa Simmons, her dating life was also making headlines.
Angela made it clear early on that she was saving herself for marriage. But as she got older, she broke her vow after announcing she was having a child out of wedlock. It wasn’t just her unplanned pregnancy that garnered criticism. Angela’s dating life has been very bumpy, from an on-again-off-again romance to one relationship that ended in tragedy.
Here’s the truth about her messy dating history.
Becoming Bow Wow’s ‘shorty’
Back in 2006, Angela Simmons reportedly began dating Bow Wow. Although they still insist they were never officially boyfriend and girlfriend, they were spending a lot of time together. Their fling came at the perfect time for Angela, who was attempting to launch a music career of her own.
After being featured in Bow Wow’s 2006 music video for the song “Shortie Like Mine,” Angela hit up the studio and recorded the rap song “Center of Attention” (watch at your own risk!).
The video was released in 2008, and things seemed to be going well for her personally and professionally. Bow took a trip out to New Jersey to have lunch with Angela’s dad. But soon after getting Rev Run’s approval, he and Angela hit a bump in the road.
Bow Wow vs. Terry Kennedy
Sorry for the blurry photo!
Angela reportedly moved on with professional skateboarder Terry “TK” Kennedy, and guess who tried to ruin everything? Bow Wow!
TK told Vlad TV he walked into a barbershop one day and was told by the people inside the shop that Bow Wow was talking crazy about him on 106 & Park. TK didn’t pay it any mind. But then he heard an interview where Bow called him corny.
TK said Bow eventually called him and apologized for starting drama. And with their beef squashed, Bow was able to wiggle his way right back into Angela’s life.
Running back to Bow
Angela and TK broke things off, and in August 2008, Blindside website reported Angela brought Bow to her sister’s 25th birthday party in Miami. Angela also made a bold move on her MySpace account by adding Bow Wow as one of her top 8 friends on the social media platform.
But by September 2008, a source told a gossip website that things between Angela and Bow were complicated. The insider added: “Angela really liked him, but he was too much into games.”
The source also stated Angela Simmons had moved on and was dating singer Lloyd, but just a few weeks later, she and Bow were spotted hitting up a bunch of New York Fashion Week runway shows together, the YBF reports. Angela was also filming segments for her family’s MTV reality show Run’s House at the time. And she spoke out about how deeply devoted she was to her Christian values.
Revealing her secret
When she and her sister Vanessa began filming the spinoff show Daddy’s Girls, Angela revealed she was saving herself for marriage. Coincidentally enough, the same year the show premiered, she and Bow Wow were on the outs again. Bow eventually confirmed their split was due to Angela not wanting to be intimate. During an episode of Growing Up Hip Hop, he said, “She was a virgin. I didn’t understand [that].”
An active dating life
She finally decided to leave Bow in the past, and in October 2009, Gossip On This website reported she was dating rapper Oscar “Skillz” Salinas of the hip-hop duo Play N Skillz. But just a few months after they were spotted shopping for cell phone accessories together, they broke up and Angela ran right back to her former flame.
In March 2010, she flew to Mississippi to watch Bow Wow play against Nelly in the Derrty Entertainment versus Cash Money Basketball tournament. And days later, Bow flew Angela out to Atlanta to attend his 23rd birthday party. That summer, they hit up a few fashion shows during Miami Swim Week. But as winter 2010 approached, Angela was ready for something real, and rumors circulated that she was dating former Chicago Bears defensive end, Julius Peppers.
According to Bossip, Angela Simmons and Julius met at a party and were casually dating each other. We’re not sure when things went sour for them, but that following year, she was celebrating her birthday in Miami with Bow Wow.
Although their fans were happy to see them hanging out again, Bow told All Hip Hop (via Vibe): “I want all the media and the press to stop saying I have a girl. Man, I’m single as a George Washington dollar bill.”
Was Lil Romeo a PR stunt?
Angela moved on once again. And in 2012, she was linked to Romeo Miller, but the press wasn’t convinced their relationship was legit.
After they were spotted on a lunch date in West Hollywood, Calif., Urban Belle website claimed Romeo was only dating her because he was tired of catching heat for dating women of other races. The website concluded that in an effort to stay on black women’s good side, Romeo’s publicist most likely arranged for him to be linked to Angela. An insider said: “By at least appearing to have dated a black woman, now he can go back to his women of choice and he won’t be penalized because he did try to date a sister.”
One month after their lunch outing, Romeo told Wendy Williams he was single, and Angela confirmed in an interview with Everything Girls Love magazine (via The Jasmine Brand) that she wasn’t in a relationship either. She said: “I’m cool and I love being single.”
For the next couple of years, she was able to fly under the radar. She was rumored to be dating businessman Knowledge Katti in October 2014. They were photographed having dinner and Knowledge was seen riding in the passenger seat of her car after they left the restaurant. Then in June 2015, she was photographed out enjoying the New York City nightlife with Ralph Lauren Polo model Morgan O’Connor, according to Bossip.
Yo Gotti shoots his shot
In October 2015, Yo Gotti released “Down in the DM.” In the lyrics, he raps about having a crush on Angela. From then on, everyone wondered if Angela would make Gotti’s dream come true and give him a chance. But in a December 2015 interview with Hot 104.1, she said she was flattered that he included her in his song. She didn’t seem too interested, but Gotti wasn’t about to back down.
That same month, Angela Simmons invited Gotti to the launch party of her new designer label Foofi & Bella. They even looked cute while posing for pictures together. The next day, Gotti sent her some flowers to congratulate her on her new business venture.
With all the pressure from fans who wanted them to hook up, Angela went on The Breakfast Club in January 2016 and made it clear that Gotti was a nice guy but they weren’t dating.
During that same interview, the topic of her intimate life was brought up once again. When radio host Charlamagne Tha God suggested that a man could possibly try to trap her by getting her pregnant, Angela said it would never happen because she’s not getting intimate until after gets married. And her words would come back to haunt her.
Falling for Sutton
In March 2016, the Growing Up Hip Hop star posted the above photo of a mystery man on her Instagram. She called him her Man Crush Every day and used the hashtag “true love.” People began speculating as to who the lucky man was, and before they could come up with the correct answer, Angela announced in April 2016 she was engaged. The identity of her fiancé was still a secret but not for long.
A month after her engagement announcement, Angela Simmons revealed her baby bump on Instagram. Internet users eventually identified her fiancé as Sutton Tennyson, and they blasted his rap sheet all over the web. Some people were concerned about the new man in her life, including her uncle Russell Simmons.
During an episode of Growing Up Hip Hop, Russell grilled Angela about the things he heard about Sutton’s past. Angela confirmed he grew up in a rough neighborhood and had been locked up on substance charges and a domestic situation. But she insisted that Sutton had turned his life around and was a real estate and business investor.
Sutton’s past wasn’t the only thing she had to worry about. Angela received a bunch of backlash for breaking the personal vow she had made. She addressed the situation in an interview with The Real. She said she had a plan, but the plan didn’t work out when she met Sutton — whom she considered to be the love of her life. Angela said she waited until the age of 28 to become intimate, and she got pregnant the very first time.
Welcoming their son
Angela told People magazine her baby was due in October, but she gave birth to Sutton Joseph Tennyson Jr. a month early on September 22nd, 2016 *side eye*
She said she was loving every minute of being a mom. However, there were rumors that things weren’t going well for Angela and her fiancé. Gossip blogs reported Sutton was cheating on her, and fans began to notice that Angela wasn’t wearing her engagement ring as much as before.
In a November 2016 interview with E! News, Angela said they had set a wedding date sometime during the summer of 2017. She said she looked forward to sharing some aspects of her wedding day on Growing Up Hip Hop. She would never get to walk down the aisle because, in December 2017, she announced she and Sutton were done.
In an Instagram post, she wrote that she realized her strength and learned how to walk away from something that wasn’t healthy.
Moving on from Sutton
A month after announcing her breakup, Angela Simmons had a fresh outlook on life and was ready to move on. In January 2018, she was spotted chilling courtside at several Toronto Raptors basketball games. And a gossip website did some digging and discovered Angela had made social media posts at the exact same locations as the Raptors’ star player Serge Ibaka.
Sadly, whatever was going on between them ended just as quickly as it started. And things were about to take a devastating turn in Angela’s life.
Sad news
In November 2018, her ex-fiancé Sutton lost his life during an altercation in a southwest Atlanta garage, a news source reports. She posted a bittersweet tribute to her child’s father on Instagram, which included a series of photos of them together as a family. In the caption, Angela wrote: “Thank you for leaving behind my greatest gift.”
Angela took some time to heal, and in March 2019, she appeared to be ready to find true love. She began posting videos on her Instagram Story of a man that many claimed to be Brooklyn Nets player Allen Crabbe. Angela and her brother JoJo Simmons even sat courtside at a Nets game, and Angela reportedly left the venue with Allen and posted a video from inside his Rolls Royce.
We’re not exactly sure when things ended for them, but during the 2019 episodes of Growing Up Hip Hop, Angela was embracing the single life, flirting with Bow Wow, and trying to navigate through her friendship with Romeo.
In a December 2019 interview with The Breakfast Club, Angela spoke out about a turbulent relationship that got physical. She wouldn’t name which boyfriend was the culprit, but she did say that it started off small and quickly escalated. That experience prompted her to create the program Pressure Makes Diamonds to help other women who are going through similar situations.
We hope Angela Simmons will fully heal from her past experiences and finally find the kind of love she’s been searching for. Until then, she’s in good company…
Messy relationship hall of fame
Ashanti still can’t figure out if she wants to be a mom of 10 kids or if she wants to be single. Read more here.
R&B singer The-Dream has finally settled down, but his past dating history is all sorts of messy. Read more here.
Jennifer Hudson and David Otunga’s relationship will go down as one of the weirdest romances ever. Read more here.
Evelyn Lozada…well, just read here and find out for yourself.
Malika Haqq and OT Genasis broke up but are expecting a baby. They seem to be getting along well for now. Read more here.
Jamie Foxx is a playboy for life. Read more here.
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