Diggy Simmons, a multifaceted talent known for his music, acting, and modeling, has largely kept his romantic life out of the public eye. Despite his celebrity status, stemming from the reality show Run's House and his subsequent successful career, Simmons has consistently maintained a private stance on his relationships, leading to more speculation than confirmed partnerships. His journey through the entertainment industry has seen various rumors about his love interests, yet he remains a figure who prioritizes discretion in matters of the heart.
Early in his career, around 2010-2012, Diggy Simmons was linked to fellow teen artist Jessica Jarrell. Reports and gossip websites circulated rumors of a romance, with some even claiming a pregnancy. However, Simmons publicly addressed these rumors, clarifying that his relationship with Jarrell was a close friendship rather than a romantic entanglement. This period highlighted his early experience with public speculation regarding his personal life and his immediate efforts to set the record straight.
Another unconfirmed, yet widely discussed, rumored relationship involved Destiny, a singer and actress of similar age to Simmons, around 2010. Their matching professions and apparent closeness fueled speculation, but like the rumors with Jessica Jarrell, this connection was never officially confirmed by either party. These early instances established a pattern of public interest in his romantic life contrasting with his preference for privacy.
The most significant and persistent romantic rumors surrounding Diggy Simmons emerged with his role as Doug Edwards on the Freeform teen drama Grown-ish, beginning in 2018. He was widely rumored to be romantically linked to his co-star, Chlöe Bailey, who played his on-screen love interest, Jazz. The on-screen chemistry between their characters, coupled with public sightings of Simmons and Bailey having lunch together in August 2019 and dancing at a Christmas party in December 2019, fueled intense speculation among fans and media outlets.
Despite the strong rumors and fan theories, particularly those stemming from lyrics on Chloe x Halle's album Ungodly Hour, neither Diggy Simmons nor Chlöe Bailey ever publicly confirmed a romantic relationship. They consistently maintained a professional stance, leaving the nature of their off-screen bond open to interpretation. This period marked the height of public curiosity about Simmons's love life, largely due to the visibility of his role on Grown-ish.
Throughout his public life, Diggy Simmons has consistently expressed a desire for privacy regarding his romantic endeavors. He rarely shares details about his personal life on social media and has often been described as keeping a low profile. In a January 2021 interview with BET, Simmons shared his views on modern-day love, affirming his belief that "long-lasting love still exists." He also partnered with Bumble, a dating app, to discuss his dating preferences and relationship must-haves, indicating an openness to finding love while still maintaining discretion about who he might be dating.
As of recent reports, Diggy Simmons appears to be single and has not been publicly linked to anyone in a confirmed relationship. His approach to romance seems to prioritize genuine connection and privacy over public display. While fans continue to speculate about his love life, Simmons remains focused on his career and his personal quest for a meaningful, lasting partnership, all while carefully guarding the details of his romantic journey from the public eye.