Keyshia Cole’s Dating History Is Actually Insane

Keyshia Cole has had one of the most interesting and headline-making dating histories in R&B. From high-profile relationships with rappers and NBA stars to rumored romances and controversial flings, the “Love” singer has been linked to some of the biggest names in music and entertainment. In this video, we take a chronological look at Keyshia Cole’s dating history, including her rumored and confirmed relationships from the early 2000s to the present day. We start with producer Chink Santana, who was linked to Keyshia during the early years of her career, as well as the rumors surrounding Santana, Keyshia Cole and Ashanti. We then look at Keyshia's alleged brief relationship with The Game, before getting into her highly publicized romance with Jeezy, including the conflicting stories about who proposed to whom. The list continues with NBA player DeShawn Stevenson, rapper Maino, and Keyshia's most significant long-term relationship with former NBA star Daniel “Boobie” Gibson. We cover their marriage, their son Daniel Gibson Jr., their separation and the lengthy divorce process. We also revisit Keyshia Cole's controversial relationship with Birdman, including the infamous 2014 incident at his Los Angeles home that resulted in Keyshia's arrest and a subsequent civil lawsuit. From there, we cover her rumored relationships with Bow Wow and Floyd Mayweather Jr., before looking at her confirmed relationship with younger rapper Niko Khale, with whom she welcomed her second son, Tobias Khale. We then get into Keyshia's brief and dramatic 2022 connection with NFL star Antonio Brown, including their “Don't Leave” collaboration, the infamous “AB” tattoo and the social media fallout that followed. More recently, Keyshia Cole dated Atlanta rapper Hunxho from 2024 into 2025. Their relationship attracted considerable attention because of their age difference and their music collaboration on “Don't Let Me Down.” Finally, we look at Skrilla, the Philadelphia drill rapper who sparked dating rumors with Keyshia Cole in July 2026 after the two were repeatedly seen together and shared affectionate photos on social media. While neither has officially confirmed the relationship, Keyshia's “Yup” caption sent fans into a frenzy. Keyshia Cole Dating History: Chink Santana – 2003–2005 The Game – 2005 Jeezy – 2005–2007 DeShawn Stevenson – 2008 Maino – 2009 Daniel Gibson – 2009–2013 Mr. Ruggs – 2013 Birdman – 2014 Bow Wow – 2016 Floyd Mayweather Jr. – 2016 Niko Khale – 2017–2020 Antonio Brown – 2022 Hunxho – 2024–2025 Skrilla – 2026–Present Game's Dating List is WILD:    • GAME's Dating List is WILD...   The Bow Wow List is MESSIER Than You Remember:    • The Bow Wow List is MESSIER than You Think..   Some relationships on this list were publicly confirmed, while others remain rumors or have never been independently verified. This video distinguishes between confirmed relationships and alleged romances wherever possible. Who do you think was Keyshia Cole's most significant relationship? #KeyshiaCole #KeyshiaColeDatingHistory #KeyshiaColeBoyfriends #KeyshiaColeRelationships #KeyshiaColeExes #Jeezy #DanielGibson #Birdman #NikoKhale #Hunxho #Skrilla #TheGame #AntonioBrown #BowWow #FloydMayweather