How do modern playboys get the girls? Is it because they’re rich? Famous? Ridiculously handsome? Here are some tips on getting girls we’ve picked up from some of the most well known modern playboys.

Jack Nicholson

is very honest about how he feels about women.  He’s certainly had his fair share of them, and at one point in time felt invincible in his confidence with getting them. “‘If men are honest, everything they do and everywhere they go is for a chance to see women. There were points in my life where I felt oddly irresistible to women.”

The actor is also known for bragging about sleeping with multiple women at once. Of course, he also admits to using viagra in such cases. Viagra might just be the secret weapon this modern playboy uses. But make sure if you’re using ED pills to do it safely and with a prescription from your doctor!

“I like each year to date a nice range of women. I only use Viagra when I am with more than one”

Charlie Sheen

Known for his crazy drug-fueled rock ‘n’ roll lifestyle this actor’s womanising ways isn’t always organic. It’s been claimed he spent $1,629,507 on hookers. The actor himself has admitted to using escorts, including pre-op transexuals.

That doesn’t mean he gets all his sex from pay-services however. Sheen has been known to date several pornographic actresses, including Bree Olson, Georgia Jones and Scottine Ross

To live like Sheen all you need is millions and millions to spend on partying, hookers and basically, live that crazy high-life lifestyle. It also helps if you’re an undisputably charismatic actor who’s also applauded for his sense of humour.

Dan Bilzarian

One guy who definitely lives up to the high-life is self-proclaimed “King of Instagram” Dan Bilzarian. This trust fund baby spends his time on private jets, at high stake poker games and in the sea or pool with bikini-clad models.

It’s funny to think it was a scandal when he allegedly slept with 16 women in 12 days when now you can see scores of women on his Instagram daily. There is definitely something appealing in that lifestyle of champagne and guns that girls are drawn to.

The party playboy offers fun and excitement, as well as exposure to his 16M Instagram followers. That being said, there’s no real evidence of how long these women last with him. If you throw impromptu private-jet party flights to Vegas every week or so, you can probably convince a bunch of Instagram models to come with you.

Dan has been blessed with a privileged life from the start and although he definitely makes bank in his own right now, he had a lot of help from that silver spoon in his mouth he was born with.

He grew up in Tampa, Florida, in an eleven-bedroom mansion that was half the size of Buckingham Palace. When interviewed in July 2014 by the radio host Howard Stern, Bilzerian declared that his net worth was around $100m (£63m)

The formality before fucking

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While I'm in the gym working on my skinny legs, @mabelynncapeluj is pouring out all my champagne

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Woke up and said fuck it, we going to Bahamas #MileHighSelfie

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Russell Brand

Russel Brand is known for being loud, married to Katy Perry once and also treated for sex addiction. He fully acknowledges that his immense luck with women comes from the fact he was famous.

” I took drugs between 16 and 19 and then heroin. I lost a lot of weight and moved from the suburbs into the city. Women were now attracted to me. I went sort of crazy with that. The sexual addiction, for me, was worse when I was clean. I think for about five, 10 years it was really bad. Listen, I’m lucky. I was famous. I’m heterosexual. I’m attracted to adult, human females. It’s not complicated. I don’t have any weird tastes. It was a good position to be in if you have that particular problem.”

Not conventionally handsome or physically fit, Brand has built up his own brand with his “unique” look of homeless bum hipster guy. After his rehab, he took on a more spiritual hippie outlook. He tries to explain the allure of sex and how it became an addition in his second book “Booky Wooky”, “this is what sex provides for me — a breathing space when you’re outside of yourself and your own head. Especially in the actual moment of climax, where you literally go, “Ah, there’s that, then. I’ve unwound. I’ve let go.” ”

Brand definitely got a lot of ladies thanks to his fame, drugs and general lifestyle. But there’s a lesson in finding your own unique identity and not being worried about looking conventionally attractive.

Hugh Hefner

Hefner pretty much birthed the word “playboy”. Although there were playboys before his time, he put a word to it. He also put sexy ladies to that word. Many would think that his success comes from his hiring of beautiful women and the fact he owned a magazine, but from interviews and his interactions, we can see just how polite Hefner was in regards to women and sex.

“Sex is the driving force on the planet. We should embrace it, not see it as the enemy.”

In one famous tweet that became a viral sensation, Hefner schooled a fan on the use of the word “bitches”. Hefner has definitely come across as charming and polite. You’d be amazed at how far you can get with girls just by being charming.

Leonardo DiCaprio

Leo is known for dating a string of top models, including Victoria’s Angels. Despite his history, he often comments that he goes for a very different type of girl. He looks for “humility, a sense of humour and not a lot of drama” and has commented,

I prefer ordinary girls — you know, college students, waitresses, that sort of thing. Most of the girls I go out with are just good friends. Just because I go out to the cinema with a girl, it doesn’t mean we are dating.

If you want tips on how to get girls like Leo, then consider hanging out at more fashion events. Getting into the fashion industry isn’t quite as hard as you might think. Of course, starting up a fashion blog, commenting in the fashion circles on social media and establishing yourself as someone cool to pick up models might be a bit too much work. But it’s also probably easier than becoming an A-list Hollywood actor.


Prince was one of the most sexually provocative idols of our times. Known for his unabashed loving, he wooed women both with his stage presence but also with his romantic side. It comes across in his songs, but he was a very passionate man.

He’s the most romantic man that I’ve ever met in my life! He’s the most romantic man ever. There’s no man that can touch him on romance. Nobody. He’s extremely romantic — you know what I mean.”  Explained his former partner Vanity

“Prince sent a limo to pick me up that night and put me front row center at the concert,” says Devin Devasquez. “I saw how sexual he was on stage. Here I was very close to the stage and he was performing the whole concert to me and licking his hand and doing sexual gestures!”

So turn up the romance guys. Although maybe don’t lick your hands sexually on a first date. Think “what would Prince do?” and “What would Prince do that I could also get away with doing?”

Harry Styles

The youngest modern playboy on our list, the former One Direction singer has been more than lucky with the ladies. Teenage fangirls have been adoring him for years, and at one point he even dated Taylor Swift.

The young singer, however, has a very high opinion of women. In an interview, he explained he thinks very highly of his young female fans. “How can you say young girls don’t get it? They’re our future. Our future doctors, lawyers, mothers, presidents, they kind of keep the world going. 

He also has a strong romantic spot. In his solo album, he admits to writing a lot of songs for one specific woman. He doesn’t name her, but he hopes she knows the songs were for her.

“She’s a huge part of the album,” says Styles. “Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it’s just for them.”

In Conclusion

Ok, so it’s going to be hard to be a millionaire playboy if you’re not born a millionaire like Dan Bilzarian. It’s also going to be tougher if you’re not an A-list Hollywood celebrity like Leonardo Dicaprio or Jack Nicholson.

But that doesn’t mean you can’t take tips from these modern playboys. A running theme with most of these men is that they have a lot of respect for women, as can be seen from Hugh Hefner, Harry Styles and Prince. Respecting women is going to definitely help your game with them.

Another great ace they have is their charm. You have classic charisma charm with a splash of humour like Charlie Sheen. You have full on “don’t-care” attitude by Dan Bilzarian which can be charming in its own way. There’s the intensely passionate charm of Prince.

Finding your own charm, your own unique pulling point is a good place to start. If Russel Brand could make girls think he was a sex god with his hobo-inspired fashion, you’ve got a chance too.