The Rehab singer was seen drinking whiskey and locking lips with former child actor-turned-rapper Aubrey 'Drake' Graham at New York's Lucky Strike Lanes and Lounge on Monday.
A source told the New York Post newspaper: "She was drinking whiskey and apple juice and making out with him all night. They were really cute together."
Rihanna is believed to have left the trendy bowling alley with Drake around midnight.
The night before, the 21-year-old beauty was spotted kissing a guy at a lap dancing bar.
Rihanna whose ex-boyfriend Chris Brown allegedly assaulted her in February took over the VIP room of New York's Flashdancers club and was seen getting friendly with one of the hunks in her party.
A source said: "Rihanna didn't get any lap dances herself, but she was tipping the girls a lot. And she was definitely with one of the guys in her group and kissing him all night."
The group allegedly spent around $2,500 in the club before leaving at 3.30am.