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...I find if difficult approaching someone when it's outside of my comfort zone. I don't know if I have the mindset or the personality to approach someone. What would be the best way to approach someone when you're a little on the shy side? Any help I can get would be great.
I think you are confident in your comfort zone because you're good at something work-related. However, your unfortunate experiences in dating women at work seem to be affecting your confidence.
At any rate, failure and rejection can and do affect your comfort zones. The best approach I think is to aim small and do it many times in a day.
For instance, when you're at a McDonald's counter and the female service crew is about to say those canned, "What's your drink sir? or "Would you like to add an apple pie [to your order], sir?"
You can say something like, "I want a vodka with some pineapple on it," or "I want an apple barbecue with sweet and sour sauce," or "Those apple pies, do they have worms in it?".
If she says, "Of course, not. Our apple pies are blah, blah, blah."
You can answer back with, "Oh, I want an apple pie with worms in it. I'll go fishing after breakfast."
The key is to write down all of the non-workplace women you meet everyday, write down what they say to you by default or by routine, think up of a fresh answer to those questions, practice saying those to yourself many times, and then say your freshly made up answer to the non-workplace women you meet everyday.
For starters, keep your answers short and say these with a very serious look (this is VERY important) on your face.
If you get a smile in 2 out of 10 interactions, forget the 8 failures and remember the 2 smiles. Next, go to another McDonald's store or place you don't go to everyday and say the routine that you've made in reply to the routine that the female service crew says.
When you get 10 smiles out of 10, then it's time to move up to the next goal. Oh, get one of those free David DeAngelo ebooks if you still don't have one.
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Approach. Open. Escalate. Isolate
Here are my two essential rules on texting that will save you tons of time and money:
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