He’s reportedly trying to ditch his reputation of dating young models

Yet Leonardo DiCaprio appeared to have no issue with partying with them as he was spotted leaving celebrity hotspot Chiltern Firehouse with model Josie Redmond at 4am on Wednesday. 

The 49-year-old actor kept a low profile as he left the London restaurant and hotel alongside the 21-year-old American model. 

Leo, who was spotted partying with another gorgeous lady earlier in the week, proved he hadn’t tired of nights out as he soaked up the atmosphere into the early hours. 

The Oscar-winning actor went incognito in a black Los Angeles Lakers baseball cap and a large grey face mask.

Two's company: Leonardo DiCaprio  was spotted leaving celebrity hotspot Chiltern Firehouse with model Josie Redmond at 4am on Wednesday

Striking: Josie looked radiant

Two’s company: Leonardo DiCaprio was spotted leaving celebrity hotspot Chiltern Firehouse with model Josie Redmond at 4am on Wednesday

He wrapped up in a black hoodie and jeans that he paired with dark trainers.  

Josie also opted for all-black as she teamed leather leggings with a sheer bra-flashing top and longline coat. 

She completed the look with chunky black boots and added a touch of colour with gold jewellery. 

Josie’s modelling bio describes her a as a girl ‘with southern charm’ due to her Tennessee roots. 

The blonde beauty lives in Los Angeles and has landed work with brands such as 7 For All Mankind and Paige Denim. 

She describes her hobbies as travelling, hiking with her dog, wake surfing and watching sunsets.  

Josie and Leo’s outing marks yet another time that the Titanic star has been seen partying alongside a beautiful young companion in recent months.

However, the Oscar-winning actor is ‘not pleased’ with the ongoing jokes and speculation about his love life – and is desperate to ‘ditch’ his image of only dating women under the age of 25 while settling down in a ‘more mature’ relationship.

All American girl: Josie's modelling bio describes her a as a girl 'with southern charm' due to her Tennessee roots

All American girl: Josie’s modelling bio describes her a as a girl ‘with southern charm’ due to her Tennessee roots

A source close to the star laid bare his frustrations over the scrutiny he faces every time he is photographed with a young woman, while revealing that Leo wants to find a ‘real’ relationship – much like the long-term romance he had with model Camila.

Yet over the weekend, Leo found himself linked to Love Island UK host Maya Jama when the pair partied together two nights in a row amid the BAFTA celebrations.

The pair were both at Chiltern Firehouse on Saturday night for Leo’s pre-BAFTAs party where they rubbed shoulders with the likes of Jamie Foxx, Neelam Gill and Taron Egerton.

Then the next night on Sunday they both attended the same BAFTA afterparty at Annabel’s members’ club, sponsored by British Vogue And Tiffany & Co.

On Saturday Maya left celebrity hotspot Chiltern Firehouse just minutes before the star – who is famed for dating women younger than him.

A few minutes after Leonardo left the same venue at 3.30am after the bash and tried to keep a low profile with his head down and face mask.

Leonardo was seen leaving the same after party at Annabel’s via the back door in the early hours of Monday morning.

Low-key: The 49-year-old actor kept a low profile as he left the London restaurant and hotel alongside the 21-year-old American model

Low-key: The 49-year-old actor kept a low profile as he left the London restaurant and hotel alongside the 21-year-old American model

Out and about: Leo, who was spotted partying with another gorgeous lady earlier in the week , proved he hadn't tired of nights out as he soaked up the atmosphere into the early hours

Out and about: Leo, who was spotted partying with another gorgeous lady earlier in the week , proved he hadn’t tired of nights out as he soaked up the atmosphere into the early hours

Casual: The Oscar-winning actor went incognito in a black Los Angeles Lakers baseball cap and a large grey face mask

Casual: The Oscar-winning actor went incognito in a black Los Angeles Lakers baseball cap and a large grey face mask

Layering up: He wrapped up in a black hoodie and jeans that he paired with dark trainers

Layering up: He wrapped up in a black hoodie and jeans that he paired with dark trainers

A source told The Sun: ‘Maya’s schedule is ridiculously busy at the moment but she is making time to work hard and play hard.

‘She had a really late night on Saturday with Leo and his mates at the Firehouse for his pre-Bafta party. She couldn’t possibly turn down that opportunity.

‘But she was ready to go again on Sunday night. Leo flew into London for the Bafta events and was out at Annabel’s, where he saw Maya again.

‘They were two of the last people left standing at the late-night event. They really know how to party.’

It comes after it was revealed that Leo is trying to shake the ridicule over his penchant for dating younger women.

‘Leo is very single right now and he is not keen on the hype suggesting that he is seeking out these very young women,’ the insider revealed to DailyMail.com.

‘He is looking for something more mature in the relationship department.’

‘It is just ridiculous because he cannot go anywhere without being linked to the youngest beautiful woman there,’ the source adds.

‘He wants to ditch this image once and for all and he is really bothered that this continues to follow him.

‘Leo wants something like he had with Camila, something real.’

Casually chic: Josie also opted for all-black as she teamed leather leggings with a sheer bra-flashing top and longline coat

Casually chic: Josie also opted for all-black as she teamed leather leggings with a sheer bra-flashing top and longline coat

Looking good: She completed the look with chunky black boots and added a touch of colour with gold jewellery

Looking good: She completed the look with chunky black boots and added a touch of colour with gold jewellery

Stunning: Josie wore her golden locks slicked back in a ponytail and donned a Chanel bag

Stunning: Josie wore her golden locks slicked back in a ponytail and donned a Chanel bag 

For years now, Leo has found himself the butt of many a dating joke – as well as facing furious backlash over his apparent refusal to woo a woman who was over the age of 25.

The furious speculation about his dating habits has been given much fuel over the past year.

Leo split with Camila just weeks after she hit the 25 milestone – and was then photographed with a bevy of young models, including 25-year-old Victoria Lamas and, most recently, 19-year-old Eden Polani.

Leo faced bitter backlash over the alleged romance with Eden – who is 29 years his junior – prompting an insider to issue a vehement denial that there was anything romantic between them.

‘They were seated next to each other at a music-listening party,’ the insider told DailyMail.com at the time. ‘There were a number of people at that event.’

He was also recently linked to 27-year-old Gigi Hadid – older than his usual type – yet it’s been said that their relationship ‘fizzled’ out.

The talented supermodel and the Oscar winner were first publicly linked earlier last year in September after attending a friend’s party together.

An insider close to the businesswoman informed the entertainment outlet that, ‘She hasn’t seen him for a while,’ and further added that the star, ‘just decided that she was done with him.’

Bikini babe: The blonde beauty lives in Los Angeles and has landed work with brands such as 7 For All Mankind and Paige Denim

Fun in the sun: She describes her hobbies as travelling, hiking with her dog, wake surfing and watching sunsets

Bikini babe: The blonde beauty lives in Los Angeles and has landed work with brands such as 7 For All Mankind and Paige Denim

While focusing on her successful career in the fashion industry, Gigi has ‘prioritized’ raising her two-year-old daughter, Khai, whom she shares with ex and former One Direction member, Zayn Malik.

‘They are at very different places in life. She prioritizes being a mom,’ a source told PEOPLE.

On what had caused the romance to end, the source simply expressed that, ‘It was never that serious anyway. It kind of just fizzled.’ 

The intrigue around Leo’s dating habits dates back decades after he was catapulted to stardom following a string of leading man roles in movies like 1996’s Romeo + Juliet and 1997’s Titanic.

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

Gisele and Leonardo at the 2005 Academy Awards

 Leo’s first high-profile relationship was with the Brazilian model, who was 20 when the pair hooked up. She broke off the relationship five years later at the age of 25.

BAR REFAELI (2005-2010) 

Bar Refaeli

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

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

Erin Heatherton

The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio in 2012.

TONI GARRN (2013-2014)

Toni Garrn

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

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

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 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.

GIGI HADID (SEPTEMBER 2022 – DECEMBER 2022) 

Gigi Hadid walks the runway in Paris in October 2022

Gigi Hadid walks the runway in Paris in October 2022

Following his August split from Morrone, it was reported that Leo had his eyes on model Gigi Hadid. The pair were seen hanging at NYC hotspots but the romance seemingly fizzled out in December.

VICTORIA LAMAS (DECEMBER 2022 – NOW)

Victoria Lamas pictured

Victoria Lamas pictured 

Leo was previously romantically linked to model/actress Victoria Lamas, who happens to be the daughter of actor Lorenzo Lamas. The pair were spotted hanging in Hollywood in late December and reportedly rang in the New Year together.



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