You're definitely on the right track by forcing yourself out of your comfort zone. Don't be too hard on yourself on the girl issue, make sure you're happy and content with yourself beforehand, and don't depend on a girlfriend to make you happy. Those relationships are symbiotic, and when they end, you'll be worse off than when you started.
To be honest on the gaming thing, keep your expectations low for that as a career, but keep your enthusiasm high for it as a hobby. Like someone said, indie developers and YouTube content producers are a dime a dozen, so you'll have to be really unique to stand out in the sea of mediocre stuff. Keep your library job for now for the steady income, and start getting serious about game development just as a hobby, nothing more. Download free trials of Unity, Game Maker, etc. and build up your scripting and coding skills. Post whatever rudimentary games you make on forums, no matter how crappy they are. Listen to feedback and advice, and keep improving. Eventually you'll see tangible evidence of yourself improving, and hopefully that'll give you the drive to keep at it. Yeah, you'll get trolled for making garbage at first, but fuck them. You'll get better, and success is the best revenge.
You can do better than a book keeper at a library, so look for a job that'll lead to a career. Unless you know a professional game developer that can get you in the door in the future, don't have your heart set on becoming a developer. But definitely stay passionate about it.
Sorry I can't give you recommendations on video gear and development books (I'm in the music industry,) but I hope that helps :)
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