Did Leonardo DiCaprio, 49, and Teyana Taylor, 33, hook up over the weekend? A new report claims the two actors got rather cozy at an event after filming a movie together all year long.
Taylor supposedly hosted a party at the venue honoring the 2024 Rock & Roll Hall of Fame ceremony. According to Page Six, the Academy Award winner and the “K.T.S.E.” singer were seen laughing together while mingling at The Stafford Room in Manhattan, New York, on Sunday, Oct. 20.
“They were dancing very closely,” a source told Page Six about the two celebrities. “They hung out the whole night and they were pretty much in a corner together.”
An insider insisted DiCaprio was “very flirty” with Taylor but they were not seen holding hands, kissing, or showing other forms of PDA inside the club. They allegedly left together around 3 a.m., though it’s unclear if they left in the same vehicle, according to the outlet.
The reported interaction took place hours after DiCaprio’s “intimate dinner” with his 26-year-old girlfriend, Vittoria Ceretti, at the Sushi Azabu restaurant.
Internet gossip about the possible NYC hookup was downplayed, noted a source close to DiCaprio’s girl, who maintains that she and Teyana are “good friends.” They allegedly celebrated Ceretti’s runway debut during the Victoria’s Secret Fashion Show earlier this week.
Apparently, DiCaprio and Taylor are friends too and have grown closer since filming for their upcoming movie “The Battle of Baktan Cross” began in January.
The Paul Thomas Anderson-directed film, scheduled for release in August 2025, also includes appearances by Regina Hall, Sean Penn, Alana Haim, Wood Harris, and Benicio del Toro.
In early February while filming a robbery scene, DiCaprio visibly slaps Taylor on her backside as she was seen laughing, fueling more speculation.
“That’s a slap and grab squeezy squeeze,” wrote one person in the comment section of The Hollywood Fix’s video on YouTube. Another said, “you can tell the second slap was not in the script…”
But in the world of Hollywood, a few believed, he was simply playing a role, stating, “It’s improvisation from Leo , that’s what makes him a great actor.”
Commenters on Page Six’s article addressed the reports of DiCaprio having a good time with Teyana Taylor while out partying in New York City.
One person stated, “I cannot comprehend, that he, almost 50, still likes to go clubbing like a 20-year-old.” A Leo defender replied, “Depends upon where you go clubbing. I was at a club on New Years in my 50s in Asia and you want to see beautiful, friendly women.”
Several people accused the co-stars of pushing the story of their late-night club rendezvous as a publicity stunt.
“Wow, he can do better than that. But don’t they always do things like this prior to a movie? So desperate for attention and ticket sales,” one person wrote.
A like-minded individual commented, “They are not together, it’s just PR for their upcoming film – gets people talking and generates interest in the movie.”
Another added, “33? She’s way too old for Leo.”
DiCaprio reportedly began dating the Italian fashion model Ceretti in 2023 after reportedly meeting her during the “Killers of the Flower Moon” premiere at the 2023 Cannes Film Festival.
She was previously married to Italian-American DJ Matteo Milleri from 2020 to 2023. The dating history of DiCaprio includes rumored relationships with Demi Moore, Gigi Hadid, Rihanna, Blake Lively, and numerous other women.
DiCaprio was in a six-year public relationship with Brazilian supermodel Gisele Bündchen from around 2000 to 2005. The then-couple famously attended the 77th Academy Awards in 2005, making their Oscar red carpet debut.
Like Leo, Taylor had a famous longtime romantic partner as well. During a 2016 interview on “The Wendy Williams Show,” she revealed that she had secretly married NBA player Iman Shumpert earlier that year.
Teyana and Iman, 34, have two children; Iman “Junie” Tayla Shumpert Jr. was born on Dec. 16, 2015, inside their home bathroom after the “Madea’s Big Happy Family” star unexpectedly went into labor.
“She came out as a wonderful surprise to everyone! Not knowing I was in labor until I felt her head… it took two ten-count pushes with my fiancé playing Dr and she entered this world into his bare hands!” the singer wrote on Instagram.
The “We Got Love” reality stars’ second daughter, Rue Rose Shumpert, was born on Sept. 6, 2020, also “in a bathroom without the assistance of a hospital!” Iman revealed.
Teyana Taylor and family for the cover of Ebony ❤️ How beautiful!!!! 🥰 pic.twitter.com/wEWyr2jfCZ
— PrettyLittleThing (@OfficialPLT) April 12, 2022
In September 2023, Teyana announced her separation from Iman. The music video director insisted they were still “best of friends,” “great business partners” and “one hell of a team” when it came to co-parenting their children.
TMZ broke the news that Taylor had filed for divorce in January 2023. It was finalized in June 2024. Court documents filed by the “Wake Up Love” singer cited Iman Shumpert’s supposed jealousy and insecurity over his wife’s fame as the cause for the split.
