Ashley Olsen was spotted "holding hands and snugging" with famed painter George Condo in New York over the weekend.
The 30-year-old fashion designer has sparked rumours she's dating the popular artist, 59, after they were seen getting cosy over dinner at the brasserie Balthazar in the Big Apple.
An eagle-eyed onlooker told the New York Post newspaper's Page Six column: "It was obvious something was going on [between them]. It looked like she [Ashley] was dining with her grandpa, but they were holding hands and snuggling."
However, this isn't the first time the pair have set tongues wagging as they also sparked speculation of a romance two months ago when they were seen at the Mercer Hotel together.
Despite onlookers stating their arrangement looked "romantic", a representative for George was adamant at the time that they had simply met up for a "business meeting" and were not dating.
The blonde beauty is no stranger to dating older men as she also romanced Bennett Miller, 49, briefly until they called time on their relationship earlier this year.
She's also dated David Schulte, Justin Bartha, Greg Chait and Scott Sartiano, and was rumoured to have romanced Johnny Depp and Jared Leto, although neither relationship were ever confirmed.
Meanwhile, George's wife Anna, with whom he has two grown-up daughters Eleonore and Raphaelle, filed for divorce last year.
It seems Ashley could be following in the footsteps of her twin sister Mary-Kate when it comes to snagging a date with an older man as she's just married her beloved beau Olivier Sarkozy, 47.
The pair first started dating in 2012 and, despite the heavy criticism regarding their 17-year age gap, they got engaged in 2014 and eventually tied the knot in November last year.