Rihanna and Hassan Jameel were first spotted kissing in Spain last June during the "Wild Thoughts" singer's vacation

A gold Grammy award is great company, but Rihanna had another hot date to afterparty for music’s big night.

The 29-year-old songstress was spotted leaving 1Oak Nightclub in New York City shortly after her rumored boyfriend, Saudi businessman Hassan Jameel, on Sunday night. The duo partied until the early morning hours, with Jameel heading home around 3:45 a.m. local time and Rihanna leaving the club shortly after.

Rihanna, who joined Kendrick Lamar on stage to accept the award for best rap/sung performance for their collaboration “Loyalty.” at Sunday’s show, was still rocking her third look of the evening, a gold crop top that tied in the front. She paired the ensemble with bold purple eye shadow and gold jewelry, including a choker necklace.

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Jameel kept things casual in a gray t-shirt and black hoodie.

RELATED VIDEO: Rihanna Spotted With Saudi Billionaire Hassan Jameel

The pair were first linked in June, when they were spotted kissing in Spain during the “Wild Thoughts” singer’s vacation. Their jet-setting romance also saw them dining at the same London restaurant in September and taking on Boston in October.

“They were super chill,” a source at STRIP by Strega at the Boston Park Plaza, where the rumored couple dined, told PEOPLE at the time. “She was super nice, relatively quiet.”

On Halloween, Rihanna was spotted with Jameel and a group of friends grabbing dinner and going bowling in Cambridge, Massachusetts, with a source telling PEOPLE the two were spotted “canoodling all night.”

Be sure to check out PEOPLE’s full Grammys coverage to get the latest news on music’s big night.

Hassan is an heir to the Abdul Latif Jameel business dynasty of Saudi Arabia. The company owns the right to sell Toyota Motor vehicles in Saudi Arabia and other Middle Eastern countries (among other ventures) and Hassan serves as the president of the charitable organization within the company, Community Jameel.

60th Annual GRAMMY Awards - Show
Rihanna at Grammys
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Rihanna also sparked rumors of an engagement last month when she rocked a sizable diamond on that finger to Chris Rock’s show at Madison Square Garden in New York City. However, a source confirmed to PEOPLE that the Doyle & Doyle antique brown diamond cluster ring is not linked to an engagement.