The "7 Rings" singer was spotted out and about with Graham Phillips on Saturday, for dinner at Carbone, a swanky Italian restaurant in New York City.
Grande dressed to impress for the night out, rocking a Burberry mini skirt paired with a black top and white, knee-high heeled boots. Phillips seemed to complement the pop star's ensemble by also opting for shades of tan and staying warm in a navy blue jacket.
This isn't the first time Grande and Phillips (who once starred together in Broadway's 13) have reunited in recent years, however. Back in 2016, the two put fans in a frenzy when they met up for dinner at Red O restaurant in Los Angeles. The former couple previously dated in 2011 when Grande was starring as Cat Valentine on Nickelodeon's Victorious.
Their latest outing over the weekend comes less than two weeks after Grande was spotted with another ex-boyfriend, Big Sean. The two, who dated from October 2014 to April 2015, were seen outside a recording studio in Los Angeles.
Meanwhile, Grande's former fiance, Pete Davidson, 25, has recently moved on with Kate Beckinsale, 45. The comedian addressed their age gap and high-profile romance during Saturday Night Live'slatest "Weekend Update."
"Apparently people have a crazy fascination with our age difference," he joked. "It doesn't really bother us, but then again I'm new to this. So if you have questions about a relationship with a big age difference, just ask Leonardo DiCaprio, Jason Statham, Michael Douglas, Richard Gere, Jeff Goldblum, Scott Disick, Dane Cook, Derek Jeter, Bruce Willis, Harrison Ford, Tommy Lee, Alec Baldwin, Sean Penn and whoever the president of France is."
"Mel Gibson, Billy Joel, Mick Jagger, Sylvester Stallone, Eddie Murphy, Kelsey Grammer," he continued. "Larry King, Larry King, Larry King, Rod Stewart and Donald Trump."
Hear more from the hilarious segment in the video below.