I'm a socially awkward loser, who has basically no friends and can't talk to girls. I've heard the best way to change is to push yourself to your limits, so what should I do that'd force me to be more sociable/outgoing? Preferably an easy to land job of some kind
Bump
You need to make a rule, if there's something you think would help you socially but you're scared to do it, you must do it. Make sure you're not going to party's and events for anyone but yourself, if you keep trying to please everyone then you come across as pandering and needy. The important thing is that you at least try something before writing it off completely, knowing that is the only way I can life with all my past failures.
You have to push yourself. It can be very hard when going out alone. Think about what would you like to do. Maybe do volunteer work or join an event that sounds interesting to you. Volunteer work can help you with job interviews. It helps when you have an answer for those dreaded "tell me about yourself" or "what have you been doing while unemployed" questions.