This Guy Challenged Himself To Chat Up 100 Women In 50 days – what did he learn?

Ciaran Callam explains why he started the ‘100 women in 50 days’ challenge and the main lessons he’s learned.

64 women down, 36 to go: Ciaran Callam takes a sip of his coffee.

“I spent 11 years of my life in relationships I shouldn’t have been in. Now, I’m 34 years old and I realised I’m not where I want to be as far as women are concerned,” he explains.

Millions of singletons might make similar confessions, but few are taking as many steps as this man towards fixing things.

The author/copywriter has challenged himself to chat up 100 women in 50 days. Two every day.

His list of successful courtships sounds like it’s straight out of a Pitbull song: Costa Rican, Romanian, Austrian, American.  

But he insists this challenge isn’t about sex. It’s about freedom.


The author/copywriter has engaged in several social freedom projects in the past.

Previously, he challenged himself to face 100 days of rejection. In the future, he plans to attend 30 nights out on his own.  

Many men would find his current challenge even tougher though. Ciaran eloquently explains why in his blog’s introduction.    

He says: “Approaching women with romantic intent is actually one of the hardest things we ever have to do and that’s the reason why the vast majority of us only ever do it while drunk.

“When a guy approaches a girl he doesn’t know, every one of his insecurities are shoved right into his face in technicolour HD and it’s in that moment that he really finds out what he’s made of.”

This self-discovery has been stretched to the extreme. Ciaran has approached women in a crowded yet near-silent Starbucks and spoke to some while they’re surrounded by friends. He’s even tried his luck in the world’s least social space – the London Underground.

The symptoms of these socially awkward situations sound atrocious: stomach cramps, crippling fear of what others will think, internal voices pleading him to pussy out.

Why would anyone deliberately seek out these difficult situations?

Ciaran explains: “At all times, men and women are going out living their lives and they see someone that they’d like to speak to, either because they’re attracted to the person or they just think the person looks cool, but they don’t.

“I think we live in a world where everyone’s scared. We have strict and rigid codes of conduct. People aren’t free. I’m just trying to free myself and show other people that they can be free too.”  


Ciaran speaks so passionately about this topic. It appears he’s prouder of actually approaching these women then he would be of sleeping with them.  

He’s been on several dates since starting the challenge, but is reluctant to discuss these. He doesn’t document them, as this would distract people from the main purpose of his project. Breaking social boundaries.  

Surely it’s a bit about the short-term rewards of sex with a new woman though? After suffering through two unhappy relationships totalling eleven years, who could blame him?  

“Every guy has this ultimate dream fantasy of being like James Bond with the ladies. I’d like to get as close to that as humanly possible, but also when I’m like 45 or 50 I’d like to have a loving family and kids,” he says.

“My future wife or long-term girlfriend. She’s out there, but I could meet her anywhere. She could be over there. I don’t want to be the kind of person who lets opportunities pass him by.”

He’s certainly making huge strides to ensure that special woman doesn’t get away.

Now I want you to do the same…

BONUS DOWNLOAD: Would you like to learn how to be fearless around beautiful women?

My ‘How To Be Fearless’ PDF features the best content from myself and other dating experts to help you develop nerves of steel around the hottest girls.

Just drop your email address in the box below to download the guide. I’ve even added a motivational video made by Ciaran himself.

The document also explains:

  • How I set out on a mission to become fearless around women

  • The science of why we’re scared to speak to gorgeous girls

  • 8 attitude shifts to kill your fear of the opposite sex

  • 17 clever conversational tricks to help you chat up women

  • What to say to a girl you just met

  • My top tip for becoming the coolest guy at the nightclub

  • The best motivational videos to spark you into action today!

You’ll also be subscribed to The London Dater newsletter where you’ll receive 7 awesome London date ideas and the best of our blog in your inbox every Monday.

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One Comment

on “This Guy Challenged Himself To Chat Up 100 Women In 50 days – what did he learn?
One Comment on “This Guy Challenged Himself To Chat Up 100 Women In 50 days – what did he learn?
  1. I think challenging yourself to take action is brilliant. Confidence is learned and earned, through action. Too often we focus on the outcome and not the action itself. We want to get to the destination before we even get on the road. If you have a goal. Focus on the small actions that it takes to find success. That is key.

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