Everyone is afraid of rejection - no matter what they say and everyone at one point in their life has been rejected. The only way its going to get easier is to go for it. If you get rejected, well I wouldn't worry too much about it and move on, since females out number males in the world :) Yes it's going to suck but you'll learn to overcome it. With the shyness. Have you tried a new outfit? Pampering yourself with something that you wouldn't normally get for yourself and then showing it off - great confidence builder!
Treat all women as if you don't care to be in a relationship with them. This is to trick your own brain into not being so intimidated. I find it is much easier to talk with women I have no chance with (married, taken, etc), because I am not worried what they will think of me or do to me.
The best thing to do is NOT ask them out when you first meet them, or think that you have to. Women like to date someone they have known for a while, or get to know them as much as possible in the first meeting. If you like her, just be friendly and greet her when you see her, ask her about herself when you are talking. Once you are comfortable with interacting without feeling the need to go for the end-game right away, then dating will happen for you. Also, the more women you are friends with, the more options you have. They all have female friends that want a good guy you know ;)
Welcome to my world. I think there are some general ideas that might help though.
1) Force yourself to do something you wouldn't normally do. Baby steps, though.
2) Play to your strengths. Me, I'm a performer. I love being on stage, and feel completely natural. Yet to look at me in life, I'm terribly shy. I think that's why I'm more comfortable on stage. If I have to introduce myself each time to 50 different people, that's 50 times I have to start the ball rolling and talk with completer strangers. On stage, you do it once, and you go on from there. Many performers can be shy in real life, for many reasons.
3) The question should probably be: "How do I get comfortable around a QUALITY woman? " See, I try to avoid the "I must have a girlfriend by tonight" desperation tactic or I'm going to get seriously depressed about any failure. Instead, I'm just trying to figure out ho to talk to women or get comfortable around them. That's hard enough without setting up that high a goal so soon.
I wish I could help you better, but I admit, I'm scared to death talking to women. I do it when I have to, but asking them out is something that I hate doing with a passion; I have every right to be terrified.
But that doesn't help my situation any, just as if I were bitter and angry at everyone. With my rough childhood, I have every right to be as nasty as I want toward people. But I'm not. While I may have the right, that doesn't mean I SHOULD do it. I've had so many mean cruel rejections and really damaging immasculating breakups, it doesn't help my situation any to be withdrawn. Sometimes I have to make an effort to go out. But I still try it once in a while.
I wish there was better advice that I could give you. But, maybe something I wrote will make everything click. Good luck to you.
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Describe your ideal first date; Where do you go? What do you wear? How does the date end?
Not a so fancy resturaunt, where we can talk deeply. After wards a nice time-taken walk on the beach.Wearing a skirt that is knee high and a shirt that low cut but not too low cut and when it becomes a little chilly my date would put his jacket around me.It begins to rain and out of no where my date kisses me,both our faces turn red,he drives me home and with a simple kiss goodnight, I go inside.
Afterwards..what will your date know about you?
That I am loving, a good listener, someone he can trust, someone he willknow will always be there for him.