How Gerard Butler cannot resolve whether or not he is the brand new Leonardo DiCaprio

Since breaking into Hollywood, Gerard Butler has developed a reputation as being something of a ladies man.

He has previously been linked to A-lister Jennifer Aniston, American reality star Brandi Glanville and British supermodel Naomi Campbell.

Most recently, the 54-year-old Scottish actor’s been spotted out and about with Sports Illustrated model Penny Lane, who is 25 years his junior.

The pair put on a cosy display while heading for lunch at the Queen’s pub in Primrose Hill this week.

It’s not the first age gap relationship Gerard has been rumoured to be a part of – as just like Hollywood’s Leonardo DiCaprio, the actor isn’t shy of cosying up to women who are years younger than him.

Here, FEMAIL takes a look at how age is just a number in Gerard’s dating life…  

2024: Gerard, 54, and Penny Lane, 29

Gerard put on a cosy display with Sports Illustrated model Penny Lane as they headed for lunch at the Queen’s pub in Primrose Hill this week.

The actor has seemingly moved on from his nine year on-off romance with interior designer Morgan Brown, whom he was last seen with in January of last year. 

Penny, who is 25 years his junior, put on an affectionate display and massaged Gerard’s shoulders during their walk to the pub. 

Earlier this year, Penny was voted Sports Illustrated Rookie of 2024 and shares an array of raunchy snaps over on her Instagram. 

According to her profile, Penny began modelling at 16 and struggled with the pressure to maintain a size zero figure. 

After restricting her diet and developing an unhealthy relationship with exercise she took a step away from her career to prioritise her mental and physical health and eventually studied to become a certified holistic health coach. 

When she isn’t modelling, Penny enjoys outdoor activities and extreme sports such as race car driving and swimming. She also works as an actress and had a small part in the Justice League franchise. 

2023: Gerard, then 53, Morgan Brown, 50

Prior to Penny, Gerard was in a nine year relationship with real estate investor and interior designer Morgan. 

The couple had been on and off for a few years after first being linked in 2014 after fans spotted them on a beach date in Malibu. 

They called time on their romance in March 2021 after splitting previously in August 2020. 

He said at the time: ‘I went through a break-up during corona so I lost a loved one in a different way, and that’s been very hard, much harder than I thought.’ 

However the pair were later seen packing the PDA in April 2021 and subsequently in January 2023. 

It is unclear when they split. MailOnline have contacted his representatives for comment. 

2014: Gerard, 44, Lizzie Cundy, 46 

Lizzie Cundy ditched Gerard after a passionate affair in 2014. The relationship ended suddenly and in 2021, via the Irish Mail, Lizzie finally revealed why.

She admitted: ‘He slapped my a*** in front of my son, who thought it was the most disrespectful thing anyone ever did. I couldn’t continue the relationship after that.’

During their rumoured romance, former WAG Lizzie took to her Instagram account to share photographs with the Hollywood actor.

Taken during outings at London’s trendy Chiltern Firehouse, one snap showed Gerard smiling at the camera while Lizzie leaned against him from behind.

‘Another fun night Gerard Butler #chilternfirehouse,’ the caption read, while a different photo posted in 2014 by Lizzie, who was married to ex Chelsea footballer Jason Cundy, showed the pair posing with friends at drinks.

2013: Gerard, 43, Madalina Ghenea, 25

Gerard previously romanced Romanian model Madalina Ghenea from early 2012 before splitting in the summer of 2013.

The actor, then 43, confirmed the end of his relationship with Ghenea, then 25, during an interview with German website Filmreporter.de.

He admitted that he was ‘not [in a relationship] at the moment, but at some point I do want to settle down.‘

A month prior, Madalina had been waxing lyrical about their love, saying that the Hollywood actor was her ‘first true love’.

She added: ‘He’s a great guy who knows how to do everything and I hope he will never change in any way.’

Miss Ghenea said on the Italian talk show Verissimo that she was ready to have children ‘right now’, explaining: ‘I’ve always wanted a family, with many children and pets.’

She continued saying that marriage to the Scot was not a necessity: ‘For me, maybe it is too early at this point.’ 

Meanwhile, speaking to Extra in March 2013, Gerard said his partner at the time was ‘amazing’, adding: ‘I met her in New York, and we hung out all night, didn’t even kiss, trying on my hat collection – I have so many hats!

‘I said “I’m coming to visit you in Milan,” and three days later, I was at her door in Milan. She was like, “Whoa!”‘

However, the Hollywood hunk was reluctant to label the model as ‘the one’, saying: ‘I’m having fun… I’m very lucky, she’s a great girl.’

2011: Gerard, 42, Brandi Glanville, 39

Real Housewives Of Beverly Hills star Brandi Glanville previously revealed she dated Gerard, who is three years her senior, for a week in 2011.

She told Danny Pellegrino on his Everything Iconic podcast in 2020 that the ‘very handsome’ and ‘lovely’ actor was horrified to find out she was on Real Housewives (RHOBH).

‘It really bothered him that I didn’t tell him that,’ she said. ‘I don’t lead with, somebody comes up to me at a beach party, “Hi, I’m on Housewives.” That’s a****le-like.’ Brandi appeared on RHOBH from 2011 to 2016, before returning to the show.

In 2018, the reality star posted a scathing blog post addressed to the London Has Fallen star after he cringed about their past hookup during a TV appearance.

Brandi began her rant: ‘So I’m not exactly sure when misogyny became so hip, cool and accepted but what I will tell you is that I won’t f***ing stand for it anymore! I’m talking to you, Gerard Butler! Honestly who the f*** do you think you are?’

‘Your behavior the other night, publicly acting as if you were embarrassed to have ever met me or had relations with me as if I were some horrid decrepit troll is not only disgusting but unacceptable. #Timesup on this kind of behavior.’

She continued: ‘Just a little advice for you moving forward Scorpio to Scorpio: Respect the women you invite into your bed and into your life. Whether you know their last name or not! Whether they are famous or not! Just be a proper human being.’

The angry open letter followed Brandi’s Twitter rant in which she told Gerard he could ‘f*** off’.

She wrote: ‘Let’s set the record straight Gerard Butler hit on me at a party Asked for my phone number called me up the next day and asked me out so if he wants to cringe now he can f*** off.’ 

‘Gerard Butler did not know my last name or what I did that is true but he hit on me and asked me out end of story. Moving on. I’m sorry but when you meet someone that clearly doesn’t know who you are, are you suppose to be a d*** and say bye I’m famous????’

This all began due to Gerard’s controversial interview which aired on Bravo the month before.

Host Andy Cohen brought up how Brandi had came on the program previously and said that she and Gerard had a relationship.

The 300 star said that when he had met her he had no idea that she was on television or had any fame at all. 

He explained: ‘It was kind of a crazy time in my life. Anyway we hung out and had fun and I never saw her again.’

Gerard said later people from TMZ had approached him and asked about his relationship with the reality star to which he replied: ‘Who’s Brandi Glanville!?’ 

The actor then continued with a laugh: ‘Because I didn’t even know her last name. So I’m like “Who’s Brandi Glanville?” She got pretty upset about that.’   

2011: Gerard, 42, Jessica Biel, 29

Gerard also briefly dated Jessica Biel after meeting her on the set of his film Playing For Keeps (which was released in 2012). 

The actor reportedly thought of her as ‘the one that got away’, according to Radarlonline in 2012.

A source said that the notorious ladies’ man, then 42, was scared off by Jessica, aged 29 at the time, wanting something more serious and bolted – a decision he has since regretted.

‘Gerard doesn’t have many regrets but not treating Jessica with the respect she deserved while they dated is one of them,’ a source close to the 300 star revealed. 

‘He genuinely believes she was the one that got away’, the insider added. ‘Jessica liked Gerard a lot, she was into his boyish nature, but she wanted something more serious. She was ready to settle down.

‘That’s why after getting close on the set of Playing for Keeps back in 2011, their relationship soon fizzled out.’

In the film Gerard plays Jessica’s ex, a former soccer star who has fallen from grace and finds himself unable to resist trying to score with the gorgeous mums while coaching his son’s team.

2010: Gerard, 40, Goga Ashkenazi, 32

In 2010, Goga Ashkenazi, then 32, was linked with the Scots-born Hollywood hunk, eight years her senior, after first meeting one another at the Cannes Film Festival, according to CBS News.

Meanwhile, a source reportedly told the Post: ‘Gerard was spotted chatting up Goga at a party in Cannes and they exchanged numbers.’

Neither Goga’s or Gerard’s reps offered comment to CBS News at the time of the rumours.

Born Gaukhar (which means Diamond) Erkinova Berkalieva in Kazakhstan, socialite Goga grew up in Moscow, the daughter of a senior Communist Party official, and was later educated at Rugby School and Somerville College, Oxford. 

Goga’s close friends include Prince Andrew. However she has always denied rumours linking them romantically.

‘Such nonsense,’ she told The Mail on Sunday in 2010. ‘Andrew has been a very good friend of mine since we met at a dinner party in 2001… He’s very clever and I don’t know why people have it in for him.’

2010: Gerard, 40, Jennifer Aniston, 40

Gerard was previously rumoured to have romanced his Bounty Hunter co-star Jennifer Aniston in 2010 – with the couple being the same age. 

According to movie buffs, the sexual chemistry between the pair is obvious in the film and the actors do share some intimate on-screen moments. 

The pair were rumoured to have been involved in an off-screen tryst while filming the flick, with a source claiming they enjoyed kisses between scenes and spent free time in Jennifer’s trailer, but at the time Gerard insisted they were just friends.

In 2018, Gerard was asked who was a better kisser between Jennifer and Angelina Jolie during an appearance on Watch What Happens Live With Andy Cohen.

The Scottish actor – who worked with Angelina in 2003’s Lara Croft Tomb Raider: The Cradle of Life – participated in a Plead The Fifth game where he was asked by the host which star was better to smooch. 

As he had already plead the fifth once, he looked pained to have to answer as he finally said: ‘Jennifer Aniston. I’m just going, you know, I’m just taking you by surprise.’

2007: Gerard, 37, Naomi Campbell, 37

Naomi Campbell and the Scots action star, who were both 37 at the time, were rumoured to be an item in 2007 when they were seen together on multiple occasions.

On one instance, an eyewitness told Canada.com at the time: ‘She came out of the hotel first and got into a waiting SUV.

‘Then a few minutes later, Gerard came out and got into the vehicle. And when they arrived back, they got out of either side of the vehicle and went into the hotel separately.’

Seemingly a friendly ex to many, Naomi was seen socialising with him at events afterwards, despite their alleged romance fizzling out.