Shad Gregory Moss, widely known as Bow Wow, has been a fixture in the entertainment industry since childhood, and his romantic life has often unfolded in the public eye. From high-profile celebrity romances to the complexities of co-parenting, his dating history reflects the challenges and triumphs of navigating love under intense media scrutiny. Bow Wow's relationships have frequently made headlines, offering fans a glimpse into the personal journey of the multi-talented artist.
One of Bow Wow's most notable early relationships was with R&B singer Ciara. The couple began dating in 2004, a period when both were rising stars in the music world. Ciara even appeared in Bow Wow's music video for "Like You," solidifying their status as a prominent young couple in hip-hop and R&B. Their romance, however, came to an end in April 2006, with reports indicating that the split was due to Bow Wow's infidelity.
Following his relationship with Ciara, Bow Wow entered an on-again, off-again relationship with Joie Chavis, a dancer and entrepreneur. Their romance began around March 2010, and they welcomed their daughter, Shai Moss, on April 27, 2011. The couple's initial relationship concluded in 2013, but they briefly reconnected in 2016. Despite their romantic separation, Bow Wow and Joie Chavis have maintained a positive co-parenting relationship for their daughter, a dynamic often highlighted by both publicly.
In 2014, Bow Wow became engaged to reality television personality Erica Mena. Their relationship was highly publicized and often tumultuous, with their dynamic frequently showcased on the reality series "Growing Up Hip Hop: Atlanta." The engagement generated significant media attention, but the couple's volatile connection ultimately led to their separation by the end of 2015. According to reports, the relationship was marked by intense highs and lows before their eventual split.
Years later, Bow Wow's family expanded with the birth of his son, Stone, in July 2020, with model Olivia Sky. Initially, Bow Wow publicly denied paternity of Stone, leading to a period of public speculation and controversy. However, a court ruling later confirmed his fatherhood. The relationship with Olivia Sky has been described as tumultuous, with public disagreements and social media exchanges drawing significant attention to their co-parenting challenges.
Beyond these long-term or highly publicized relationships, Bow Wow has had several other notable connections and rumored flings throughout his career. He confirmed a past "hooking up" arrangement with reality star Kim Kardashian, which he reportedly kept secret for a period. He also briefly dated Angela Simmons, maintaining a friendship after their split. Additionally, he was in a relationship with Kiyomi Leslie, which was also featured on "Growing Up Hip Hop," and rumors circulated about a possible romance with singer Keyshia Cole in 2016.
Most recently, Bow Wow has confirmed his relationship with Jade Pinkett, the niece of actress Jada Pinkett Smith. While their relationship was publicly confirmed in early 2024 during an appearance on the "Club Shay Shay" podcast, Jade Pinkett's social media posts hinted that they had been together for approximately two years prior to the public announcement. Bow Wow indicated that he initially preferred to keep their relationship private. The couple has openly discussed the possibility of marriage, signaling a serious and potentially long-term commitment. This relationship marks a new chapter in Bow Wow's romantic journey, as he continues to navigate his personal life in the public eye.