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Shy Guy? How To Get Some Guts


Too tongue-tied to approach women? Try these confidence-boosters from a once-timid guy who was determined to turn his love life around—and did.

By Neil Strauss

everal years ago, a friend and I devised a plan to meet women. Since we were too intimidated to start conversations with the array of beautiful, interesting prospects constantly passing by on the street and in the subway, we thought we’d start somewhere less advanced. So we met in the lobby of a youth hostel one Saturday afternoon. We figured the guests there would be more than excited to meet two nice guys who could show them around the city.

We sat there for almost two hours and talked to no one. As all manner of students, backpackers, and leggy Scandinavians went by, we knew everything we wanted to say to start a conversation in our minds. Yet our mouths wouldn’t move. We left with our heads
If you’re not one of those guys who always says the perfect thing on the spot, then prepare a script.
hung in shame, forced to a dreadful conclusion: Once a wallflower, always a wallflower.

But that was then; this is now.

A few years ago, I decided to take a more proactive approach to de-shying myself. I hunted down the so-called greatest “ladies men” in the world and begged for help. (It’s funny how I could be so aggressive with men but so shy around women.) I called them, sent them emails, and signed up for any classes and seminars they offered, wherever those might be. When I found a few who seemed to have something substantial to offer, I began hanging out with them and picking their brains for everything they knew. And I was transformed from shy to socially comfortable. To save you the trouble of traveling the world and hanging out with some of the unsavory (and savory) characters I did, here are some tips on getting some guts.

Act confident (even if you don’t feel that way)
The two words of advice you’ll hear the most: “Be confident.” This is usually delivered as if it’s an easy-to-follow directive, like, “Finish your meal.” But one can’t just be confident on command, right? Well, maybe you can be.

I once wrote a book with Marilyn Manson. And he shared his philosophy for success with me: “If you act like a rock star, people will treat you like a rock star.” The same applies to social interactions: Fake it till you make it. Act as if you were secure, attractive, charismatic, fun to be around, and deserving of people’s attention and time. Imagine yourself to be someone else if you have to—I actually got hypnotized to believe I was fifty feet tall and made of indestructible steel. And I had a piece of paper full of cheesy suggestions for an improved attitude — “I deserve the best the world has to offer” — that I’d look at from time to time. To be honest, saying and repeating these things doesn’t make them true, but after you start to have a few successful interactions, you might just be surprised to find yourself actually starting to believe them.

Prepare a script
If you’re not one of those guys who always says the perfect thing on the spot, then start thinking of the perfect thing in advance. Prepare a script, like a telemarketer making a sales call. Some of the ice-breakers I kept handy — based on the idea that everyone likes to give their opinion — included gathering suggestions for names. I’d say my friend rescued a three-legged cat from a shelter; what name should it be given? Or that a friend was opening a 70s memorabilia shop—what name should it go by? Before I even went out to meet women, I’d practice the conversation-starters with friends, so that I was comfortable saying them.

When you’re talking with your friends and tell a story that makes everyone laugh, write it down and keep it on a list. This way, you’ll never be stuck for something to say after your
When you tell a story that makes everyone laugh, write it down. This way, you’ll never be stuck for something to say.
opener, when that conversation with someone new starts to wane. “Oh my God! Guess what happened to me,” you can interject, and then tell your story.

Push yourself through the pain period
When it comes to unlikely people to turn to for dating advice, Arnold Schwarzenegger would definitely be one of them. But while watching the movie Pumping Iron, I discovered the motivation I needed to get out of my head and into the real world. He said that what separates the competent bodybuilders from the true champions is that the champs are willing to go through what he calls the “pain period.” This means pushing yourself outside of your comfort zone — to a place your body and mind might not necessarily want to go — and putting up with the pain because, in the long run, it will make you great.

So I applied the same technique to my interactions with women. Whenever I was scared to approach one, I tried to push myself through the fear. What helped was having a good friend with me, whom I’d instruct at the beginning of the night to force me to approach strangers. For the first few nights, I actually told him that I’d pay him a dollar every time I wussed out. This motivated him to make it hard for me, and it motivated me to work harder because I was running out of money.

So the next time you find yourself in a conversation with a new person, and things start to get awkward or you feel like you’ve run out of things to say, push yourself into the pain period. Try to keep the conversation going for at least five or ten minutes. You’ll probably surprise yourself. If not, there’s always another person with whom you can practice chatting.

Handle awkward moments with ease
Even if you find yourself stuttering, asking the same question three times or saying something stupid, there’s a solution: Pretend it’s her “fault.” Take a deep breath, and say, with a big smile on your face “Stop it. You’re making me nervous. I can see you undressing me with your eyes. I’m not a piece of meat, you know. I have a brain.” She’ll know you’re joking and appreciate your sense of humor. It’s amazing what a woman’s smile will do for your confidence.

That said, if you feel awkward, if things aren’t going well or if the people you’re talking to are rude, here’s the last piece of advice you need. Say three words: “Pleasure meeting you,” and leave politely. You never know when you may be talking to them again. Occasionally, I found that even when someone was rude, if she later saw me having a fun, animated conversation with other people in the bar, she’d come over and apologize, and I’d have another chance with her.

For me, the interesting thing is that in two years of approaching thousands of women, nothing bad happened. As long as I wasn’t rude, overbearing, or creepy — and as long as I was considerate to the men in the group — not only were there no fistfights, but even the rejections were polite. No one is going to hurt you. Chances are, your only enemy is yourself. So get out there, give it a try, and get social.


Neil Strauss is the author of The Game: Penetrating the Secret Society of Pick-up Artists and other books.
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