HE is Hollywood's most prolific lothario with a penchant for younger women.
And now, thirty years after dating her older sister, Leonardo DiCaprio spent the night partying with Lottie Moss at London's Chiltern Firehouse.
Spies at the celebrity retreat told MailOnline how they sat together before leaving in the early hours of Wednesday morning.
An onlooker said: 'You've got Leonardo and Lottie in the same room, of course they gravitated towards each other.
'They were chatting and giggling until the early hours when it was time to end it. They left the club in the early hours after having a great time.
Thirty years after dating her older sister, Leonardo DiCaprio (pictured) spent the night partying with Lottie Moss at London's Chiltern Firehouse
Spies at the celebrity retreat told MailOnline how the actor and model (pictured) sat together before leaving early on Wednesday morning
“It got people talking, they're both celebrities having a good time.”
Earlier in the evening, DiCaprio, 49, attended a special screening of his latest blockbuster Killers Of The Flower Moon at the East Room in London, alongside his co-star Lily Gladstone.
He later headed to Chiltern Firehouse – a restaurant and late night bar popular with A-listers like Bella Hadid, Joan Collins, Dua Lipa, Mark Ronson, Winnie Harlow and Noel Gallagher – wearing the same black button-up jacket and a matching sweatshirt .
The actor arrived first ahead of Lottie, 25, who arrived slightly later than the Hollywood star.
Lottie partying with DiCaprio will likely alarm her older sister Kate, who dated him 30 years ago. Lottie wasn't even born yet when the two stars had a brief affair in December 1993, shortly before she started dating Johnny Depp.
The pair met as young models in the US when they were teenagers and although they spent a lot of time together, it is believed their romance was short-lived.
On her Instagram on Wednesday, Lottie posted photos of herself wearing new hair extensions that she thought she had done before her night with DiCaprio.
On Tuesday evening she also celebrated her birthday with her model friend Aine Sweeney Byrne.
Lottie partying with DiCaprio will likely alarm her older sister Kate, who dated him during a brief fling in 1993
An onlooker said: 'You've got Leonardo and Lottie in the same room, of course they gravitated towards each other'
DiCaprio is reportedly currently dating Italian model Vittoria Ceretti, 25, who friends of the star say he is 'in love with'.
Last Friday evening, the couple was seen at the star-studded Art Basel festival in Miami
Vittoria was also by his side for his 49th birthday party last month, with a guest list of A-listers including Beyonce and husband Jay-Z, Lady Gaga and Kim Kardashian, Salma Hayek, Chris Rock, Kate Beckinsale, Zoe Kravitz and Channing Tatum. Rita Ora, Zoe Saldana and Snoop Dogg.
Lottie dated Made In Chelsea star Alex Mytton for nine months in 2017. She has also been linked to The Vamps drummer Tristan Evans, Brooklyn Beckham and Capital DJ and TV presenter Roman Kemp.