It gets easier over time, trust me. There are two things that will compound the anxiety and further your stress over approaching:
1. Trying to be perfect
2. Not try and make a fool of yourself
Most people dread feeling embarrassed and try to put on a "perfection" act in order to try and hide what they feel on the inside. In social situations they will cross their fingers hoping that they don't mess it up.
A way to get around this and get very very comfortable approaching random people is to go out with the intention of embarrassing yourself. Talk to a guy normally for a minute and then pick your nose. Go out with the most ridiculous outfit you can think of that will cause you to get red in your face.
Do this until you no longer care about how you look in the eyes of others. One lesson you will learn is that there are no consequences to "screwing" things up. Our minds create worst case scenarios in situations like this. "If I screw this up or make a fool of myself then this will happen" "or that will happen". Going through your fears will put your mind on the sidelines for a while and help you realize two things:
1. There are no consequences
2. You CAN handle anything. You could get laughed at in front of an entire group of people and it won't bother you. You could accidentally fall down while talking to the guy and it won't matter.
We are born as social creatures. Our species thrived because of our ability to come together and help one another out in packs. Fear of embarrassing yourself and running the risk of getting kicked out of the pack in ingrained in all of us. The key is work on ridding yourself of this instinctual drive and learn that there are no consequences.
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