How to Conquer Your Shyness with Women In 5 Easy Steps
1. Start Talking and Flirting with Women Who Are Working
Waitresses, cashiers, clerks, etc. These women deal with humanity all day long (just like most of us) and will take a shine to any flattery, attention or casual conversation you can provide.
If they treat you like crap they're liable to come under fire from their bosses and if they're trying to sell you something they'll usually use flirting as a sales technique (clothing stores are great for this).
Women in the workplace are my A-#1 pick for starting to build your self-esteem and rapport with girls.
I was at the mall on Tuesday and the woman at Banana Republic was so pleased by my bright smile and amiable banter that she "accidentally" put her register keys into my bag. When I went to return them after discovering this at the gift-wrap station I felt good enough to ask her to coffee. She accepted and I left with her number afterwards.
Smile and chat with every girl you meet in a service situation. It's a great start.
2. Test Your Approaches with Personal Ads
Respond to some personal ads with a phone call. These women have already let the flag fly that they're interested in meeting someone for a romantic relationship.
Call and leave messages testing out different approaches you're preparing for your real-world arsenal. Measure your success by the phone calls you get in return. Be polite if they return the call and take the time to explain what you were doing.
You'll have some pissed off ladies but more will think it's sweet and forgive easily or offer advice. Some will even pine for you because of this.
3. Perfect Your Conversation Skills with Online Chat
Online chat is the boon of every cowardly lion with a modem. Chat will help you brush up on your conversation skills.
Asking for advice from the girls on a dating channel or girl-talk spot will come off as creepy at first. But once you become a friend (through politeness and sincerity) you'll have a gaggle of 'sisters' who are dying to have you hook up with someone and care deeply about your romantic success.
You become the Ken doll. It's a short but frozen-palmed step from there to real life.
4. Read and Study Cosmo Magazine
I'm not kidding. Buy Cosmo. Read Cosmo. Send a subscription to your house in your mom's name if you have to but this magazine is the single most pernicious influence on women in America. Learn what women are berating themselves over and what they want in love/dating.
You will feel better about yourself simply because you don't face 1/10th of the relationship worries that girls do. You will also find that women absolutely *adore* men and think about sex constantly.
Better descriptions of oral sex than Penthouse forum, too.
5. Practice with Homely Girls
You can work on your self-esteem and the ease with which you approach girls by going after the ...uhm... not-so-attractive ones. These girls are starved for flattery and attention. You can approach them sincerely and openly and not have your raging hormones getting in the way.
This is still almost as frightening as going after random attractive girls on the street but you asked for small steps. Also (according to Cosmo) 59% of girls meet their boyfriends through friends. An ugly girl will have two or three attractive or *hot* friends. If you're an object of their affection, they'll play matchmaker.
There, start small with that. You're not going to go from Charlie Brown to Casanova overnight so no, Just Do It is not that simple. What you have to overcome is this pattern of getting bogged down in minutiae and little procrastinations that keep you shy and keep you lonely.
Nobody's going to write a script for you and nobody's going to hold your hand. You have to act now and until you come back with a positive status report I'm done with my advice.