E! News has learned the former lovebirds spent Friday night together at NYC hot spot Sons of Essex prior to attending the MTV Video Music Awards Sunday at Brooklyn's Barclays Center.
"Drake came in around 10 p.m. with 10 people and had four large security guards. Rihanna came about an hour later, alone, not counting her security," a source tells E! News of the twosome.
"They sat in a back room, the lights were dimmed, and there was sort of a barricade of tables blocking their group off," the insider adds. "Drake and Rihanna sat right across the table from one another. They were avoiding photos, and the security kindly asked some fans to leave, because they were trying to get too close," noting how the pair seemed to only talk to one another.
The group ate lobster tacos, crab cakes and surf and turf, while enjoying shots of Canadian Club, Watermelon Jalapeno Margaritas, and other specialty cocktails at the Lower East Side hangout.
So were the musical pals—who were previously involved in somewhat of a love triangle with RiRi's ex-Chris Brown—showing any signs of PDA?
"It seemed very casual," the source spilled. "Rihanna was wearing a black T-shirt and shorts. Drake was wearing a flannel shirt and a ball cap."
The eyewitness also adds the pair left a "generous" $500 tip before leaving separately.
Rihanna departed "about 20-30 minutes before he did," the source said.
In June, the 26-year-old rapper opened up about his infamous feud with Breezy, calling their beef "embarrassing" while dishing on the alleged NYC nightclub brawl that went down in June 2012, reportedly over the "Stay" singer herself.
"Two rappers fighting over the woman. He's not even a rapper, but still, it's the last way you want your name out there," the erstwhile Degrassi: The Next Generation star says, alluding to the now-infamous run-in at W.i.P. club.
"It distracts from the music. But he's made me the enemy, and that's the way it's gonna stay, I guess."