DDG’s Dating History: Inside the YouTuber's Most Talked-About Romances

Social media star DDG has built a name for himself in the rap game, but his dating life has kept him just as much in the spotlight as his music. From social media stars to high-profile singers, the YouTuber-turned-rapper has been linked to several famous women over the years.

Despite his eventful love life, DDG says he would advise men in their 20s to stay single. “It’s best for you to be single in these years of your life so you can really grind,” DDG said on the No Ordinary Podcast. Adding, “Get your ducks in a row first and grind and not have no restrictions.”

And while DDG may be focused on stacking his paper these days, he can’t deny his checkered past. Let’s take a deep dive into DDG’s relationship history and the women who have made headlines alongside him.

DDG’s most famous romance has been with Halle Bailey, one-half of the R&B duo Chloe x Halle, and the star of Disney’s The Little Mermaid. The couple first sparked dating rumors in early 2022 when fans noticed them together at Usher’s Las Vegas residency. By March of that year, DDG made it Instagram-official, sharing a sweet birthday tribute to Halle. Their relationship seemed solid, with the two frequently supporting each other’s careers.

The pair welcomed their son, Halo, in December 2023, but things quickly went south. Rumors of a breakup surfaced in late 2023, fueled by social media unfollows and cryptic posts. In December 2024, the YouTuber confirmed their split.

“After much reflection and heartfelt conversations, Halle and I have decided to go our separate ways,” he wrote on Instagram (via Billboard). “This decision was not easy, but we believe it’s the best path forward for both of us.”

Before Halle, DDG was linked to rapper and social media personality Rubi Rose. Their on-and-off romance made waves in 2020, but it wasn’t without its share of drama. The two were known for their messy social media exchanges, with Rubi accusing DDG of playing games and DDG shading her in his music.

Their situation escalated in early 2023 when Rubi accused DDG of letting Halle wear one of her old shirts, sparking a heated exchange online.

“Having [your] b---h where my clothes is crazy lol,” Rubi tweeted (via XXL). Adding, “I like Halle, DDG a weirdo tho fasho.”

Though DDG denied any foul play, the drama fueled even more speculation about unresolved tensions between him and Rubi.

DDG’s relationship with YouTuber Kennedy Cymone was one of his earliest high-profile romances. The two started dating in 2017 and quickly became a fan-favorite couple on social media. By 2018, DDG proposed, making their engagement one of the biggest YouTube moments at the time.

Unfortunately, their romance didn’t last, and they called off their engagement later that year. While neither has spoken in detail about the breakup, Kennedy has hinted that things didn’t end on the best terms.

DDG was also rumored to have had a brief romance with singer Emaza Dilan, but this relationship flew under the radar compared to his other high-profile pairings, according to Famous Fix. While details remain scarce, fans speculate that they had a short-lived fling before he moved on to more public relationships.