Not sure if this qualifies as a 'life hack', but I used to have absolutely zero confidence with girls. In my desperation I turned to the 'pick up artist' phenomenon to see if I could learn anything to help.
Honestly, if you read just a few of the books out there, like Mystery Method or The Game, you should pick up everything you need. Dont spend $$$$ on seminars or 'coaches'. I got pretty good at talking to girls, but I still had the terrible phobia of opening, or initiating contact. Once the first 'Hi' was uttered, everything was easy but it was getting that first 'hi' that killed me because I always feared rejection.
A few years went by and I discovered online dating. POF, Myyearbook, okcupid...etc. All free and casual sites where you can message girls (or guys) and if they reply, that 'hi' was out of the way and jackpot.
A few tips though:
Always make girls skype with you before you go on a date. Best way to find out if shes super fat or hairyor has a unibrow or is secretly a dude...etc.
Get used to phone calls. Lots of guys dont enjoy long conversations with girls because gossip inevitably comes up. Develop a taste for it (but keep it classy) or you will come off as boring.
Dont pretend to like stuff you dont just to win points. It backfires horribly (if youre just in it for a one night stand this isnt an issue but for real relationships, just be honest). If you pretend youre too cool to game and she finds your bedroom is covered in D&D posters, you start to look dishonest. Its 2014, lots of people are way more... understanding of geek/nerd culture than you know.
First few dates should be
super casual. My first two dates ever were movie nights where we met at the movies. Terrible idea. In a movie you are stuck in a chair with nothing to do but sit quietly and that can get awkward if you aren't already comfortable and somewhat intimate with your date. Instead, window shopping at the mall while joking around in shops like hot topic and spencers can be very fun. It also is very public so everybody feels safe. Its free to walk around. And you can gauge their interest as they see things. More than once I had what looked like uptight preppy girls drag me into Victorias Secret and offer to try things on.

Im sure most of the people on the forum dont need this advice, but Im sure there are a few guys that are in my old, lonely shoes. I hope you guys use this and find some happiness.
Im now happily married to a smokin hot Texas girl who makes more money than I do and we have a beautiful little girl (and more on the way). Life is good. Dont settle for less.