“THE FEAR OF JUST APPROACHING A WOMAN IS INSURMOUNTABLE”
New book gives tips for shy men
// Leah Scheitel

I’m sure every guy, shy or not, feels nervous when approaching a woman, but when you’re love-shy the feeling of just approaching a women is insurmountable,” said Christopher Gray on Global Toronto’s Morning Show, “You see a woman you’re attracted to and you feel like there is nothing you can do about it. You feel helpless.” It’s these feelings of helplessness that Gray addresses in his book, From Shy to Social: A Shy Man’s Guide to Personal and Dating Success. The author based the book on his own experiences of being extremely “love shy”, to the point where it was crippling his social life.


“I wrote it after I had such a rough time socially, such a rough dating life, and I went looking for answers on how to fix it,” he explained. “Basically, I detailed my journey on how I fixed my social life. Once I reached this level of normalcy, I thought it might be good to detail my journey and some of the methods I used to help some of the other guys that might be suffering from the same problem.” Gray thought that if he had such success in revitalizing his social life and conquering shyness, maybe his experiences could help other shy men do the same.

Book Tips

The book covers various topics including how to gain confidence, improving personal presentation, various methods of meeting women, and exercising social skills and tips from expert pickup artists. The first chapters of the book are dedicated to pinpointing the roots of shyness, what causes it, and how to overcome it. Understanding the problem is the first step to fixing it, and these chapters give some real insight into social awkwardness. Although the book is designed for the male reader, it does provide some perspective to females as well.

The author’s inspiration for the book was his old social life, which he describes as lonely and mundane: “My social life was so dismal. I found that after I started working full time, I was not making any new friends, I was not dating, and I was just coming home after work and watching TV or surfing the web. It was due to my shyness. I was resisting invitations to go out because I was so uncomfortable in social situations, especially with women I was attracted to.” Currently, he describes his social life as “pretty much normal.” He goes on dates, has friends, and interacts with others in cafes or bookstores. Gray embarked on an 18-month research period, over which time he talked to five different dating coaches and various psychologists about ways to ease social awkwardness. “A lot of the research was my own trial and error, figuring out what works and what doesn’t.” He also cites different authors and experts throughout the 200 pages.

Amongst the book is a list of assignments, each one slightly more difficult than the first. The assignments were designed to help the reader become more comfortable around women: “They do become more difficult. You have to get yourself out of your comfort zone in order to improve,” says Gray. “The most difficult part for me was actually approaching a woman and starting a conversation. It’s almost like a wall that you have to scale. Once you do it, and you do it a few times, it gets easier and easier.” The first assignment is to get yourself on the Internet more, where you are in the comforts of your own home, but still reaching out to people online. This is easy in comparison to assignment seven, where he challenges the reader to approach 50 women in ten days. It also features tips on grooming and appearance, gaining confidence, improving your walk, party etiquette, and how to approach women at bars, versus book stores, versus coffee shops.

Today, there is an abundance of ways to meet people: online dating, speed dating, and singles clubs, among others. According to Gray, one method is not better than any of the others, but the trick is to try them all to find what works for the individual. “Internet dating is popular and can be successful if you present yourself well in your profile,” he says, “but my favorite way is to approach a woman directly in bookstores, or other common places.” Gray prefers this method because if he sees a girl at a place that he enjoys, like a bookstore, he already knows that they share a common interest, and he can see how she carries herself in real life. The book shares many insights into what women want. Gray talks about many relationship myths, like how women are only attracted to the “bad-boy” type. “Women want bold men,” he writes, “or if that word is too far away from where you are right now, they want decisive men. This doesn’t mean that they want a tyrant that always wants his way, but someone that is not wishy-washy.”

Gray does generalize about women throughout the book, and while he is correct in some cases, not all women want “bad-boy” types, or want to be pursued in non-social situations, like at a bookstore. This generalization may lead some men astray, and the book would benefit from a direct female view of what she wants, instead of a male view of what all women want. Although some of the tips may apply elsewhere, the book is focused on helping men interact with women. It’s not designed to help a gay man or a straight woman with their social lives: “You can be a shy woman, and guys will still approach you. But if you’re a shy guy, you’re still expected to make the first move,” Gray explains.

Self Help

“I never thought I would write one. It was only after I had success that I considered it,” Gray explains about writing a self-help book. “I’ve read self-help books before on dating and I didn’t find them to be that helpful because most of them don’t target the problems that shy men face, so I thought that this book would break new ground, and help out the shy guys.”

Gray was never planning to write a self-help book. He was working as a professional freelance writer, mostly in the business sector. It was only after he revived his own social life did he think that his experiences could help others. The book was released in November of 2011, and is a self-published project, which is becoming more popular medium amongst writers. “It was a trial by fire experience,” Gray says of self-publishing. “Every writer needs an editor.” He says that hiring the right people, such as an editor and cover designer, is the key to a successful self-published book. A self-help book designed to rejuvenate a man’s dating life has a market, but like other books in the self-help genre, people can question how effective it actually is. There are an abundance of self-help books on the shelves, all claiming to be the key missing tool to improving lives. Because there are books to improve virtually every aspect of our lives, it is easy to get intimidated and overwhelmed when looking in that section. Besides reviews and testimonials, there is little to convince the readers that it will actually help improve their lives. What assurance is there that we’re not just going to spend $20 to stay in the exact same situation that we’re trying to get out of?

Testing the Tips

To test the theories in From Shy to Social, I invited my friend Andy out on a Thursday night. Andy is a relatively shy 23-year-old guy who rides his bike everywhere. We work together at a snowboard shop, and one day a cute girl came in with her bike. Andy was very intimidated and too nervous to talk to her, so he went and folded sweatshirts in the men’s section instead of approaching her. Over dinner, I briefed him on the book, and gave him a crash course on the assignments. Wanting to start off slow, my main point to him was to smile at every girl he thought was attractive and to say, “Hello.” This was based on assignment four from the book. My goal that night was to get Andy a phone number.

At the Backstage Lounge on Granville Island, they were serving Bowen Island Lager for $1.60, and had live funk music. Andy noticed a girl sitting at a nearby table. There were different guys around her, but she didn’t look particularly interested in any of them. “I want to talk with her,” he said, pointing her out. I patted down his cowlick, fluffed his collar (there is a whole chapter dedicated to presentation and grooming tips), and sent him off. As he walked past her on his way to the bathroom, he made solid eye contact and smiled, and on his way back to the bar, he smiled at her again. Although other guys were swarming around her, it looked like she was eager to see Andy, and they continued making eye contact from across the room while we sipped beers. Excited that he was eye flirting with a cute girl, he wanted to move on to the next step. I told him to initiate a conversation with her, but quoted the book in saying to keep the focus on her, not to ask what she does, and to keep the conversation flowing. After he went to talk to her, it was 20 minutes before he returned, and there was a large smile on his face afterwards. There was one on mine too, but that was probably because he left me at a bar that was serving $2 beers. Andy continued to have various conversations with her throughout the night, and whenever they saw each other on the dance floor, they would flirt. When we left at the end of the night, Andy had her number in his phone. He was convinced, and I will be getting him this book for his birthday.

From Shy to Social hopes to help guys get over the fear of talking to women they find appealing, which is a fear that even the most confident of guys can understand. “You’re afraid that you’re going to come off looking like a jerk,” says Gray on talking to women. The dating world is intimidating for guys and girls alike. This book can help guys put more numbers into their little black books, and also make it easier for girls, so they don’t have to hear pick-up lines like, “My name is Doug. That’s GOD backwards with a little U in it.”


//Leah Scheitel, writer
//Graphics by Katie So

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