Everytime I plan on telling the girl I like that I like her, I end up chickening out. This isn't the first time either. I got nervous asking out my crush to prom in high school and almost didn't go through with it. When I asked her out, I couldn't do it in person so I did it over text and she said no. Could that be why I can't do it now?
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First, don't tell girls that you like them. It's kind of a selfish act, and it's a high-risk move. It's even worse if you do it through text, since you can't measure her feeling (it's easier to do it when she's kissing you and snuggling up with you, e. g.). Only way that usually works is if the girl already really liked you, otherwise she might try to shut the door in your face.
Just ask them out, spend time together, and let those feelings grow for each other (or not, it may fizzle out, no biggie, move on to next girl).
Second, the reason people get afraid here is because they've developed too strong of an emotion and hope of success, become too tied to outcomes. It's like if you married the woman in your dreams, your dreams are completely misaligned from reality. That's too much pressure to try to make your dreams real with some girl you barely know.
In those cases, people always want to look for signs that the other person likes him/her, because they're trying to get a better idea of the odds to work up the courage to do anything. People turn into cowards when they perceive a low success rate and are terrified of negative outcomes. They become braver if they think they have a high success rate but are still terrified of the negative outcomes.
The secret: people who don't get spineless and can just casually talk to a supermodel *don't care* that much about outcomes. If they ask her out and she says she's busy, no big deal. They didn't marry her in their head, they like her a little bit, but whatever -- on to the next girl. Embrace this attitude and you'll no longer be all awkward around the opposite gender, and you'll even be able to have a number of female friends who think you're a great guy without some kind of odd tension there.1