Florence Ifeoluwa Otedola, globally recognized as DJ Cuppy, has captivated audiences not only with her music and vibrant personality but also with her often-publicized romantic journey. As the daughter of Nigerian billionaire Femi Otedola, her relationships have frequently been under the spotlight, offering glimpses into the complexities of love in the public eye. Cuppy has been remarkably candid about her dating experiences, from high-profile celebrity romances to more private encounters, navigating the pressures of fame while seeking genuine connection.
Early in her career, DJ Cuppy was linked to various personalities, though some relationships remained largely unconfirmed by her. One such rumored connection was with Nigerian musician Sean Tizzle. Reports from outlets like Buzznigeria and Legit.ng indicated that Tizzle had a crush on Cuppy, even sharing a suggestive post about her. However, Cuppy was reportedly unhappy with the post, and Tizzle clarified they were merely friends, despite his admitted admiration. This early speculation set a precedent for the intense public interest in her love life.
Another prominent figure with whom DJ Cuppy sparked dating rumors was British professional boxer Anthony Joshua. The two were frequently spotted together on dates and vacations, both in the UK and Nigeria, leading to widespread speculation about a romantic involvement. Despite the numerous public appearances and the undeniable chemistry observed by fans and media, neither Cuppy nor Joshua ever publicly confirmed a relationship. This unconfirmed but highly visible connection highlighted Cuppy's association with high-profile individuals and the media's keen interest in her romantic life.
One of DJ Cuppy's most public and significant relationships was with Nigerian footballer Victor Anichebe. Their romance garnered considerable media attention and was a widely discussed affair. The couple's relationship lasted for a notable period, with Cuppy often sharing moments of their time together on social media, making it clear they were a serious item. However, their relationship eventually came to an end in 2017. According to reports from Legit.ng, the primary reason for their amicable split was the challenge of long-distance, as Anichebe was playing professional football in China while Cuppy was shuttling between London and Nigeria for her career. Their breakup was a significant event in her public romantic history, marking the end of a highly visible partnership.
Following her relationship with Victor Anichebe, DJ Cuppy was linked to Asa Asika, a prominent figure in the Nigerian music industry and Davido's former manager. Their relationship was described as on-and-off, indicating a period of intermittent connection and separation. While details of their specific timeline are less clear than her relationship with Anichebe, their connection was widely reported by various entertainment news outlets, including Legit.ng and Buzznigeria, confirming another public romance in Cuppy's evolving dating history.
In a significant development that captured widespread attention, DJ Cuppy became engaged to British professional boxer Ryan Taylor in November 2022. The proposal, which occurred at an award ceremony in Abu Dhabi, was widely publicized through videos circulating on social media, showing Taylor going down on one knee to propose. Cuppy enthusiastically accepted, and the couple shared a public kiss, confirming their engagement. This marked a new and serious chapter in her romantic life, with many fans expressing excitement for her. The engagement was a major topic of discussion, with some reports even suggesting wedding plans for 2023.
However, the engagement to Ryan Taylor was relatively short-lived. By July 2023, reports began to surface, and eventually, DJ Cuppy confirmed that her engagement had ended. In December 2023, during a Women in Management, Business, and Public Service (WIMBIZ) conference in London, Cuppy publicly addressed the breakup, stating, "Such is life" and expressing optimism for her future. The split was widely reported by outlets like Vanguardngr and Naijabeats, who noted the public's curiosity about her next steps. Later, in October 2024, Cuppy reacted on social media after Ryan Taylor posted videos of his baby mama and child, seemingly unbothered by the development, indicating a complete closure to that chapter.
Throughout her romantic journey, DJ Cuppy has often shared insights into her dating philosophy. In a candid interview with The Zeze Millz Show in 2021, she revealed that she had dated "almost all kinds of men," even mentioning a bus driver, and shared that she found some of these connections through a paid dating app. This openness about her dating experiences, including using apps, has made her relatable to many. She has consistently expressed that she seeks a partner who is genuinely caring and funny, maintaining an open-minded approach to dating.
As of recent reports in July 2025, DJ Cuppy is single but has stated she is "talking to people." In a viral video, she clarified, > "I’m not dating right now but I’m talking to people… may the best man win." This statement, reported by MP3bullet and Gistlover, indicates that while she is not in an exclusive relationship, she is actively exploring potential connections. Her current status reflects a period of discernment, as she continues to navigate her love life in the public eye, always with a blend of candor and grace. DJ Cuppy's romantic history is a testament to her journey of self-discovery and her pursuit of love, marked by public romances, rumored flings, and a significant engagement, all while maintaining her unique voice and presence in the entertainment world.