The first thing in life you need to learn:
All women go for the top 20% of men. ALL OF THEM. And since men aren't too fussed about looks of women (as long as they are slim and have passable faces), and women are extremely fussed about a man (ie only want the top 20%), it's very hard for you to compete with so many things going against you.
What defines a man in the top 20%? LOoks. Money. Status.
Work on gaining all three and at that point, you don't even need to go out, just open up a tinder profile and invite girls to your house who'll be all over you.
Don't delude yourself with all that confidence rubbish, a good looking man who's nervous, shy and Unconfident will still get a lot of play as long as he can pick up on basic social cues.
First of all you need to hit the gym and go on a cut. See if that makes a difference to your face, get a good haircut to compliment your face and wear clothes that compliment your body (which you'll acquire through consistent gymming )