Members get unlimited access to all our most
valuable content long before the masses. Exclusive access to newly released gear and tech and entrepreneur secrets delivered to your inbox monthly. All free. No BS.

How to Date Like a Bad Boy

Sailun Tires

From Han Solo to Russell Brand to Prince Harry, women love a bad boy. The confidence. The swagger. The Millennium Falcon.

On the dating scene, bad boys get girls giggling, twirling their hair, and giving out their numbers. But the odds of women swooning over you—a nice guy—is slim, right?

Well, to quote Han Solo, “Never tell me the odds.” As a dating coach, I’ve helped hundreds of guys channel their inner bad boy and attract beautiful women—while still being total gentlemen.


There’s a paradox at play. The truth is, women like good guys, not arrogant jerks. In a Glamour poll, 33% of single women said “loyal and lovable” was the category of men they most wanted to date. “Bad boys” finished second to last, at 6%.

But women want it all—the nice guy with a bit of bad mixed in. This is good news. There’s no need to buy a Harley or to cover your arms in tattoos. Just be you, while following these 5 simple rules, and start dating the girls once reserved for bad boys.



What draws women to rogues and scoundrels is authenticity. They’re attracted to raw, real, unfiltered men. So lean into what makes you unique. If you’re a nerd or a single dad or a hipster, don’t hide it. Own it. Flaunt it. Feature it.

When I met my client Ken, he was 25 and had never kissed a girl. A college instructor, he’s funny and smart, with a deep knowledge of Greek literature. (Most guys quote Homer Simpson. Ken can quote Homer’s Odyssey.)

Ken was afraid to put his sweet, silly, brainy self out there, but when he did girls loved him. He approached women using knock-knock jokes, and they cracked up. He had deep conversations about Plato. Girls were grabbing his phone, punching in their numbers, and insisting he take them out. One night, he met a Gwyneth Paltrow lookalike on a rooftop bar—and they made out. His first kiss ever.

Be 100% authentic. Countless guys parrot the same pickup lines they read on the Internet. But only one person can give a girl the authentic experience of you.



There’s a great scene in Goodfellas when Ray Liotta takes Lorraine Bracco on a whirlwind date at the Copacabana, guiding her down corridors, through the kitchen, and to their table. She’s mesmerized because he’s taking her on a well-planned adventure. (OK, it doesn’t hurt that he’s doling out C-notes.)

When it comes to first dates, never say, “So what do you wanna do?” Have a plan. Pick a place she’ll like, and have a second spot in mind for a night-cap. Know where you’re leading her. Variety is good. Start with, say, cocktails at an upscale lounge and finish with shots at a fun dive. Give her an experience.

And talk about your other plans: for your future, your career, your life. Ambition is attractive. Women love a man with a plan.



Bad boys are a little cocky and like to tease. Take Hugh Grant’s rakish book publisher in Bridget Jones’s Diary, who needles Renee Zellweger for wearing “mummy panties.”

Girls like it when you pull their pigtails. So tease her, playfully. It’s not about “negging” women, like sketchy pickup artists teach. It’s about connecting. Teasing the girl invites her to spar with you, and banter can send chemistry through the roof.

My client Trevor came to me because could not get a second date, so we added teasing to his repertoire. When he met Becca, a beautiful brunette chef, he busted her chops (playfully) for being late for their date, and for her “Real Housewives” addiction. She loved it and gave as good as she got. An hour in, she crawled onto Trevor’s lap and kissed him—as every guy in the bar watched in envy.

Not a bad first date.



Bad boys have a unique style—Adam Levine’s tattoo sleeves, Russell Brand’s scarves and unkempt hair. Clarify your personal brand (see No. 1) and express it through the lens of your style. This instantly tells women who you are, helping you attracts girls who like your type.

My client Rich has an artsy, James Franco vibe, but his clothes and hair didn’t reflect that. We overhauled his look with a spikey hipster haircut, white V-necks and retro, ’50s-style sweaters. Rich attracted an amazing girlfriend and now feels more like himself.



I once met a stunning Maxim model who summed up what women really want. She said the men she encountered were either too arrogant and selfish, or too afraid to even talk to her. “I just want a nice guy with a backbone,” she said. “Nice guys are sexier than 6-pack abs.”

It takes a backbone to be authentic, to approach, to be vulnerable, to lead on a great date, to tease, to hold her hand, to go for the kiss.

Become that guy and you can date like a bad boy and still be a good man.


Written by: Connell Barrett

Dating coach Connell Barrett is the founder of DatingTransformation. He helps men attract amazing women as their most authentic, confident selves. To book a free call with him, go to




Get the latest Swagger Scoop right in your inbox.

By checking this box, you confirm that you have read and are agreeing to our terms of use regarding the storage of the data submitted through this form.

Leave a Reply

Your email address will not be published. Required fields are marked *