"Grown-ish"'s Diggy Simmons's Dating History

Image Source: Getty / Frazer Harrison

“Grown-ish” is officially back with a refreshing new season filled with a handful of both familiar faces and new characters. Among the actors returning to the beloved sitcom is Diggy Simmons, known for his role as the charming, driven Doug Edwards in the series. As Doug, Simmons stars alongside Chloe Bailey, aka Jazz Forster, who was his love interest in “Grown-ish” up until season three.

Outside of his role on the sitcom, Simmons maintains a low profile on social media and keeps his personal and romantic life private. Ahead of his return to “Grown-ish” for season five, let’s take a dive into who the actor has romanced over the years and his current relationship status.

Who Has Diggy Simmons Dated?

Information about Simmons’s love life is pretty limited. The star was rumored to be romantically linked to his “Grown-ish” costar Bailey shortly after they started sharing the screen together back in 2018. In August 2019, the two were seen having lunch together, and that December, they were spotted dancing together at a Christmas party, according to Vulture. Outside of these few occurrences, the pair were not seen in public together, which cooled rumors of their potential relationship.

Image Source: Getty / Kelsey McNeal / Freeform

By June 2020, however, fans were back to speculating about their relationship after Bailey and her sister, Halle, made some suspicious comments on an Instagram Live video. While reading a fan question that asked if either of them had dated an actor from “Grown-ish” in real life, Halle immediately pointed to her sister to answer, to which she deflected and said, “What?!” While rumors of the two dating were strong, neither Simmons nor Bailey ever confirmed anything.

Who Is Diggy Simmons Dating Now?

As of July 2022, it appears that Simmons is single. The actor and rapper shares little about his personal life on social media and has not been linked to anyone publicly. The “Grown-ish” star isn’t shy about flaunting his romantic side, however. In a January 2021 interview with BET, Simmons shared his view on modern-day love, saying, “I think long-lasting love still exists. 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.”

Simmons doesn’t hold back when celebrating romance, especially on Valentine’s Day. When asked about his ideal Valentine’s Day, he revealed it should consist of “a great meal, great flowers, and great gifts . . . I go hard with Valentine’s Day. I treat Valentine’s Day like Christmas. And a surprise. I can’t ever say what it is, but it’s always different. It always varies. I never pull out the same thing. I love the surprise.”

Simmons may not be as open about his personal or romantic life, but in his professional life, the artist is only growing more popular and building his career. Catch Simmons as Doug in season five of “Grown-ish,” which airs Wednesdays on Freeform staring on July 20.

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