The whole point is that even when you have confidence issues, you gotta put them aside and work through it SOMEHOW.
People with balls get what they want in life. Nobody ever got anywhere just talking about something, it's about doing it.
With the way I am, I'd sooner suggest finding her on FaceBook and if she has mutual friends with you, you're already ahead of the game. You can bull**** your way in and be like.. "Hey, aren't you the girl in my _______ class? You came up on my suggested contacts based on who we both know mutually." Ask some sort of question following that, whether it be asking "What's up", "how's it going", or "I'm nervous about this assignment at hand" and it'll open the door for conversation. It won't seem awkward to her which is key and (if she's a decent human being who can talk to anyone without issue) it'll get your foot in the door, period.
Being a big guy and having confidence issues myself, I can tell you it's much easier to hide behind a screen and get the ball rolling. I will tell you a lot of the females I've met have been through online dating. I don't think it's any different than going somewhere and talking to someone, because in the end you're still talking to them. They can't see the nervous looks on your face or that you're jittery or this or that. They just see typed out words and it's much easier to make conversation. From there, you can talk, learn their interests, and skip that whole awkward first meeting thing and then when you do meet for the first time in person, you're that much further ahead in the game with her. In their head, they see that you're talking, you aren't nervous and when they meet up with you, it'll also be much more comfortable with them. The name of the game is comfort. Women will do a lot when they are comfortable around you.
When I'm giving advice to friends who don't have any real experience because they're scared, I just explain it this way. Your three C's you need.
Comfort. Confidence. Common grounds.
If you have these, you can get anywhere with 98% of the females out there.
And if it's just a female in general he's after then he can just skip this bull**** and go straight to online dating with that said.. Honestly, I won't hesitate to admit that between my ex (July 13) and this girl (October 6ish) , I met up / banged 8 different girls in that time frame and did much more with others. While they might not have been the one I ended up with, it kept me busy and without that lonely feeling. I don't know his situation , but the computer might be a better alternative.. thus my "sack up and do it"
Doesn't matter how you do it, long as it gets done. That's my take.
Keeping in mind that this is coming from a guy who looks like this and can get what he wants. ^
That's how you know the game plan works.
edit:
there's no other real advice to be given. swim or sink time.