He has famously never dated a woman over their mid twenties.
Yet Leonardo DiCaprio appeared to have his head turned by two women of the age of 27, as he spent the evening flirting up a storm with models Rebecca Donaldson and Lilia Weddell.
The 48-year-old actor has recently been linked to 23-year-old Victoria Lamas, but the famed ladies’ man was not seen with the actress on Thursday evening.
Partying: Leonardo DiCaprio appeared to have his head turned by two women of the age of 27, as he spent the evening flirting up a storm with models Rebecca Donaldson and Lilia Weddell
Leonardo had recently returned from a racous holiday in St Barts where he had been partying with a slew of beauties.
After landing in Miami on Wednesday, the Oscar-winning star looked worn out, yet soon perked himself up and found the strength to go out partying again later that evening.
Leo was earlier seen out in Miami in a plain white T-shirt and grey shorts, yawning as he was driven by his chauffeur.
Glamorous girls: Lilia (left) looked incredible in a tiny denim skirt paired with a white T-shirt and black blazer while Rebecca dazzled in a silver glittering midi dress
Dating history: This graph displays Leonardo DiCaprio’s age and the corresponding ages of his former girlfriends and flings
After heading home for a few hours, and no doubt enjoying a long nap, the actor was later seen heading to Papi Steak to host a party for him and his very glamorous coterie of female friends.
Leonardo was joined by actor Jamie Foxx, 55, and a gaggle of females, including Scott Disick’s model ex Rebecca and Lilia Weddell, who has been romantically linked to Drake.
Leo donned dark denim bottoms with a cream belt, adding a black button up and a baseball cap.
Fun times: After heading home for a few hours, and no doubt enjoying a long nap, the actor was later seen partying with Lilia Weddell and Rebecca Donaldson
Low-key look: Leo donned dark denim bottoms with a cream belt, adding a black button up and a baseball cap
No time to sleep: The party kept going until the early hours, with Leo seen chatting to Rebecca and fellow model Lilia on the patio of Forte Dei Marmi at 4AM
He wore a face mask and kept his head down as he entered the restaurant ahead of his party.
The party kept going until the early hours, with Leo later seen chatting to Rebecca and Lilia on the patio of Forte Dei Marmi at 4AM.
One model not in attendance was 23-year-old Victoria Lamas, who he has recently been linked to.
Holy smokes! Leo was seen puffing on a cigarette and enjoying a glass of wine at the party
Fashionable friends: Also in attendance at the party was British Vogue editor-in-chief Edward Enninful who donned all-black and looked in high spirits at the party
They were seen together three times in a week late last month following reports that Gigi Hadid was not ‘serious’ about their short-lived romance.
While the Hollywood hunk and Hadid were reportedly still dating in late November, the superstar appears to be moving on with Lorenzo Lamas’ daughter.
Leo’s outing with Victoria comes after he ended his four year relationship with Camila Morrone, 25, in August, a source close to Leo claimed to The Sun.
It’s a hard life: Earlier in the day Leonardo was seen yawning with exhaustion after returning from his racous holiday in St Barts where he had been partying with a slew of beauties
Snoozy: Leo was earlier seen out in Miami in a plain white T-shirt and grey shorts, yawning as he was driven by his chauffeur
Under wraps: He kept a low profile by donning a trucker cap and a grey face mask with shades
Victoria was born on April 24, 1999 – two years after Leo’s iconic 1997 film Titanic was released – and is the daughter of actor Lorenzo Lamas and model Shauna Sand.
Lorenzo, 64, is best-known for playing Lance Cumson in the 1980s soap opera Falcon Crest, which ran for nine series.
He also starred in the 1978 movie Grease as minor character Tom Chisum, who was the captain of Rydell’s football team.
New love interest: One model not in attendance was 23-year-old Victoria Lamas, who he has recently been linked to
Meanwhile, Shauna, 51, is an American actress and was Playboy magazine’s Playmate of the Month for May 1996.
Victoria looks set to follow her famous parents’ footsteps as she is an aspiring actor, who is trying to carve out a name for herself on screen.
She has a passion for photography and is also an artist who creates incredible acrylic and ink works of art.
Leonardo DiCaprio’s Dating History
The Django Unchained star has famously made a habit of never dating any woman over the age of 25.
GISELE BUNDCHEN (1999-2004)
Gisele and Leonardo at the 2005 Academy Awards
Leo’s first high-profile relationship was with the Brazilian model, who was 18 when the pair hooked up. She broke off the relationship five years later at the age of 23.
BAR REFAELI (2005-2010)
Bar Refaeli
The actor’s relationship with Bar Refaeli ended after 5 years of dating – coincidentally the same time the Israeli model turned 25.
BLAKE LIVELY (2011)
Blake Lively and Ryan Reynolds
The current wife of Ryan Reynolds dated Leo for just one year – when she was 23.
ERIN HEATHERTON (2012)
Erin Heatherton
The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio in 2012.
TONI GARRN (2013-2014)
Toni Garrn
German-born model Garrn was just 21 when she and Leo broke up after two years of dating.
KELLY ROHRBACH (2015)
Kelly Rohrbach on the set of Baywatch
The Baywatch reboot star was 25 when she and DiCaprio dated from June until around December of 2015, with the break alleged to be a mutual decision
NINA AGDAL (2016-2017)
Nina Agdal and her ex Jack Brinkley Cook
Things ended between Leo and the Danish swimsuit model after she hit 25 in 2017.
CAMILA MORRONE (2017–2022)
Leo and Camila out and about in New York City in May 2018
Leo and the model-turned-actress began dating just months after his split from Nina Agdal. The were reported to be more serious than ever at the start of the coronavirus pandemic, but the two reportedly split over the summer of 2022.