Druski was spotted enjoying a high-profile night out at Madison Square Garden during Sunday night’s matchup between the New York Knicks and the Los Angeles Lakers, and he wasn’t alone. Druski arrived at Madison Square Garden with model and adult film star Sky Bri, with the two taking courtside seats together for the highly anticipated game. A source told Complex that the pair appeared comfortable and playful throughout the night, laughing, leaning in close, and flirting as they watched the action unfold, giving off clear date-like vibes.
Druski’s most publicized relationship in recent years was with rapper and model Rubi Rose. The two went public in 2024, though fans initially questioned whether the romance was real or part of a comedic storyline. That speculation grew when Rubi later suggested on social media that the relationship had been staged for publicity.
Months later, however, Rubi revealed during a livestream with Adin Ross that their relationship had actually been genuine. She explained that she had downplayed it publicly after the two fell out and her feelings were hurt, calling it a reaction she later regretted. Rubi also shared that she and Druski had known each other for nearly a decade, dating back to their high school days.
Druski previously hinted at their breakup in a radio interview, admitting that dating someone of Rubi’s caliber came with pressures he wasn’t fully prepared for at the time.
Sky Bri, meanwhile, has also been linked to several high-profile internet figures over the years. She was previously connected to influencer and podcast host Mike Majlak and later made headlines after being associated with YouTuber-turned-boxer Jake Paul.
Neither Druski nor Sky Bri has publicly addressed their appearance together at the Knicks-Lakers game.