But it seems Hollywood legend Al Pacino is completely unfazed by Leo's reputation as a womaniser – after introducing the heartthrob to his step-daughter, Camila Morrone, 21 – and going on numerous double dates with them.
The Godfather actor, 77, has been in a relationship with Camila's mum, Lucia Sola, for nine years. At 42, she's a year younger than her daughter's boyfriend Leo.
The foursome have been out to dinner twice in the last couple of months – and spend the weekend hanging out on a luxury yacht together on the French Riviera.
And it’s not just Leo’s relationship with Camila that’s blossoming – it seems Al is completely supportive of his step-daughter's relationship and seriously steamy PDAs – and has taken Leo under his wing while they film Tarantino's new film, Once Upon a Time in Hollywood.
Here we look at how the bromance between Leo and Al has blossomed through their double dates.
Leo, his girlfriend and her hot mum holiday in St Tropez
Over-zealous in-laws are one of the many pitfalls of a new relationship, but for Leo, it seems the actor can’t get enough of glamorous Lucia and Al.
Notoriously private about his love life, Leo was happy to openly attend a double date night with Camila, Al and Lucia at Beverley Hills Greek restaurant Avra in June.
Al and Leo clearly hit it off – and pictures of their budding bromance have been flooding social media.
Leonardo and Al have both starred in gangster films, and have both worked with renowned director Martin Scorsese – Leo in 2002 for Gangs of New York, and Al for The Irishman this year.
Just four weeks after their Greek restaurant double date, the pair returned to the same restaurant – ditching Camila and Lucia for La Lakers star, LeBron James.
Clearly not a lady to be shunned from the limelight, Lucia then joined Leo and Camila on their romantic holiday in St Tropez last week.
Usually surrounded by a harem of models, Leo was on his best behaviour as his girlfriend’s lookalike mum joined them on board a luxury yacht.
They were seen dining at celeb hotspot Le Club before walking down a jetty and boarding the glamorous vessel.
Although Leo appeared to be trying to go incognito in a grey hooded top, he happily helped Camila and Lucia, both dressed in white, on board.
PDAs, snogging and romantic getaways
It's clear to see Leo has a lot of respect for Pacino – and he's clearly a big fan of his step-daughter.
The blue-eyed Lothario has been dating Camila since mid-December, and the couple haven’t been able to keep their hands off of each other since – jetting to Colarado together for a romantic white Christmas, and snogging during Eminem’s set at music festival Coachella in June.
If Leo’s lovelorn looks and embraces are anything to go by, IMG model Camila could finally be the one to tie him down, despite their 23-year age gap.
The end of the "pussy posse"
If they do settle, this could see the demise of Leo’s squad of Hollywood bachelors – "the pussy posse" – which includes David Blaine, Toby Maguire, and Entourage’s Kevin Connolly.
It was long-term pal Toby Maguire who Leo turned to after splitting with ex-girlfriend Nina Agdal before last year’s Cannes Film Festival, and the two were seen at Esquire’s Golden Globes party in January, shortly after Leo met Camila.
But since Al arrived on the scene, it seems his Hollywood squad have fallen by the wayside in favour of his new friendship with acting legend Al.
It could get awkward…
Leo and Al are currently filming together for Quentin Tarantino’s new movie, Once Upon A Time.
And if their bromance turns out to be nothing but a fling, there could be awkward repercussions for the both of them.
In the film, Al is thought to be playing big time agent Martin Schwarz, who takes on the business of a washed-up actor (thought to be Leo).
It’s set for release next year, which would mean maintaining a relationship with Al…and Camila…at least until then.
The next leap in their relationship will be Leo introducing Camila to his beloved mum, Irmelin Indenbirken – the true love of his life.
He has a history of double dating with Irmelin, who visited the set of Once Upon a Time last fortnight, but the last girlfriend given the privilege was model Bar Refaeli, who he dated for five years until 2011.
Could there be a triple date on the cards? If Camila’s relationship with Leo continues the way is has been, we’re sure Al will insist on it.
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