I think go ugly early is a little advanced for a guy lacking confidence.
Honestly, go ugly and stay ugly.
I'm talking fatties.
Go for the surest of sure things. You'll find out that even those don't always work out, but after a few you'll settle into your groove and get used to the routine of going out and hitting on girls and not overly caring or letting it wreck your night depending on the outcome.
Then start to work your way up. You won't realize it, but you are more confident now and it comes across that way to girls. Gradually work your way up until you're actually talking to girls you like. Boom. Married.
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