According to the tab, Leo, 41, and 24-year-old Sports Illustrated hottie Nina Agdal have rekindled a romance that began back in 2014.
Over the weekend, the pair was spotted at Goldberg's Famous Bagels and the Montauk Point Lighthouse while enjoying "a romantic weekend" together in the Hamptons.
And although Nina's social media accounts are full of smiley pics from Montauk, an insider close to Leo has dismissed the report, telling Gossip Cop Leo and Nina simply both happened to be the Hamptons at the same time for a mutual friend's birthday celebration.
If that's the case, the two have a bit of a habit of showing up at the same place at the same time.
In May, they both partied at Up&Down in New York on the same night -- a few days after they both attended the amfAR Gala in Cannes.
Leo's long and storied history of surrounding himself with young, leggy models -- most of them blonde -- dates at least back to 1994, when he reportedly dated his "Basketball Diaries" co-star, Brittany Daniel.
Since then, the actor's been linked to a seemingly endless stream of models including Helena Christensen, Amber Valletta, Gisele Bundchen and Bar Refaeli. More recent names on the list have included Erin Heatherton, Toni Garrn, Kelly Rohrbach, Chelsey Weimar and Roxy Horner, plus a rumored fling with (gasp) non-model, Rihanna.
Despite the changing roster of ladies on his arm, Leo hasn't ruled out the idea of settling down someday.
"The truth is, you can't predict marriage," he said in a January edition of Parade. "You can't plan it. It's just going to happen when it happens."