Angela Simmons is getting candid. The entrepreneur, reality star, and mother sat down with Shannon Sharpe on the June 24 episode of Club Shay Shay, where no topic was off limits. During the wide-ranging conversation, Simmons reflected on her decision to remain a virgin until age 28, her past relationship with Bow Wow, the heartbreaking loss of her son’s father, Sutton Tennyson, and whether she’d ever consider spinning the block for round two with an ex.
Angela Simmons On Club Shay Shay: Why She Waited Until 28 To Lose Her Virginity
When the topic of her virginity came up, Simmons revealed that she initially planned to remain abstinent until marriage, a decision heavily influenced by both her faith and her father, Joseph “Rev Run” Simmons of Run-DMC.
Looking back, Simmons recalled a conversation she had with her father and sister Vanessa when she was still a teenager.
“I hold my Dad in a very, very high regard,” Simmons explained. The message stuck with her, but it was later reinforced during a church service.
“And then, one day, I remember going to church and they were discussing all these things about waiting for marriage, and I was like, ‘You know what, I’mma wait,’” the Pastry Footwear entrepreneur continued. “It went from my dad telling me, to hearing it in church, and then I was like, ‘I’m just gonna wait until I meet the right person for marriage,’” Simmons continued. “Then, time kept ticking, and then I was like, ‘Dang, I’m 28. This is crazy.’”
Simmons ultimately lost her virginity to her then-fiancé Sutton Tennyson, and the pair welcomed a son together. Their relationship later ended, but tragedy struck years afterward when Tennyson was fatally shot outside his Atlanta home in 2018 following an argument that escalated into gunfire. Michael Williams was later sentenced to life in prison in connection with the killing.
Mourning Sutton Tennyson And Raising Their Son Without Him
Perhaps the most emotional part of the interview came when Simmons reflected on the death of Tennyson and the impact it continues to have on her and their son.
Although the couple had already ended their relationship before his death, Simmons said the loss was devastating.
“We actually weren’t togehter when it happened, we had broken up, but it’s one of those things that to me till this day is so surreal because I could have never imagined that this would be my story. But the hardest part is looking at your son and knowing that would have been his best friend. He’s so much like his dad.”
Simmons recalled feeling completely numb when she learned what had happened.
“I was waking up everyday like this can’t be real,” she added, revealing that it took years of therapy to process the tragedy and begin healing.
The most difficult chapter, however, came years later when her son discovered information about his father’s death online. According to Simmons, her son eventually looked up the story himself and called her while she was on her way to an event.
“He looked it up himself…We were like, how do we as a family tell him what happened without it affecting him,” she recalled.
Eventually, Simmons had to explain everything. Her son was heartbroken, she said, and she found herself having a conversation no parent ever wants to have.
“I could have never imagined that’s the conversation I’m having with you at 7 years old,” she said.
The Real Reason Things Didn’t Work Out With Bow Wow
Simmons also revisited her longtime connection with rapper Bow Wow.
Fans of Growing Up Hip Hop may remember Simmons previously revealing that the pair dated briefly but never officially became boyfriend and girlfriend because Bow Wow “wasn’t ready.”
During her conversation with Sharpe, Simmons shared that her decision to remain a virgin played a role in why their relationship never fully progressed.
Sharpe also noted that Bow Wow has since reflected on their relationship and admitted Simmons was “ring worthy.”
For Simmons, hearing that was flattering.
“I like that,” she gushed. “I know I will one day be an amazing wife that makes me happy that a man can see that.”
Would Angela Simmons Ever Get Back Together With An Ex And Get Married?
When it comes to love, Simmons isn’t completely closing any doors. The reality star’s most recent high-profile relationship was with rapper Yo Gotti. After dating for more than two years, the couple ended their relationship in early 2025.
Simmons later revealed on Angie Martinez’s In Real Life podcast that she ended the relationship, which was difficult, but that it was for the “best.”
Still, when Sharpe asked whether she’d ever “spin the block” on an ex, Simmons admitted she’s keeping an open mind.
“If it makes sense—why do I get asked this?—if it makes sense,” she chuckled. ”I will be lying to myself if I say I don’t know. I don’t necessarily have intentions to say, ‘Look let me go be with this person, Imma marry them.’ But you never know, right, it could be.”
In other words? Never say never. Watch the full episode below.
What do you think about Angela Simmons’s Club Shay Shay interview? Thoughts?
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