Rihanna Rocks High Ponytail & Hangs Out With Pal A$SAP Rocky In 1st Pics After Hassan Jameel Split

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Rihanna, 31, seems to be doing fine since her break-up from Hassan Jameel, 31. The “Rude Boy” singer was spotted hanging out with her longtime friend — and rumored former flame — A$AP Rocky, 31, at the 2020 Yams Day Benefit Concert in New York City on Friday, Jan. 17! The pair looked like they were having a blast as they laughed and smiled while seated in the audience, and were later seen goofing off in a photo backstage. The duo were both holding fake money in honor of Yams Day, which celebrates the life of ASAP Mob founder Steven Rodriguez — a.k.a. ASAP Yams — who died in 2015 at just 26.

The outing marks Rihanna’s first sighting since news of her break-up with Saudi billionaire Hassan Jameel after nearly three years of dating. Rihanna and A$AP were casual for the occasion, as Rih rocked gorgeous curls in a high ponytail and rocked a cool-girl pair of combat boots. She finished her look with a cozy jacket, perfect for the cool NYC temperatures. A$AP, who is Harlem native, matched her vibe in Los Angeles Lakers bomber jacket, purple sweatshirt and white sneakers. Known for his bling, the rapper rocked his signature layered diamond and gold chains to elevate the look.

While Rihanna and A$AP have never confirmed a romantic relationship, rumors have swirled about the pair for years. Rihanna starred in his sexy 2013 video for “Fashion Killa” and, with all the PDA, they definitely seemed like a couple! Reportedly, they were even seen kissing off camera during filming. The pair have continued to hang out over the years, and recently, the Barbados native even flew to Sweden to watch his show in December!

That same month, the rapper — born Rakim Mayers — rocked a Fenty ensemble as he posed for photos with Rih at the 2019 British Fashion Awards. To add to the list, Rihanna was also seen hanging with Rocky and the mob in October at the Rolling Loud festival.

Interestingly, Rihanna’s former flame Drake, 33, was also at the Yams Day Benefit Concert on Jan. 17! The Toronto-born rapper posted up a storm on his Instagram story from the event, and even shared a video of him hanging out with A$AP. Drake presented his long-time friend with a diamond-encrusted pendant to mark the occasion, which apparently cost around $150,000.