You will only ever live once. That means you should take risks. YOLO doesn't mean: "you only live once so let's go do something life threatening and stupid that will probably end our life! Hey look a cliff! Let's see who can hang off of it the longest without falling!" YOLO means: "i am never, ever going to be back in this moment at this second, this day, in this frame of mind, with the knowledge and experiences and emotions I have right now, so I'm going to take an emotional risk right now because it won't **** me, and my chance for a new experience is NOW."
What you could do, is go someplace public where you rarely go so that chances are you won't see the people who are there ever again, where you know people your age will be (example: starbucks or something) and find a girl who is sitting alone and who just looks like an interesting person. Not just pretty, but truly interesting. Sit down next to her or across from her and just literally say: Hi. wait until she looks up and makes eye contact with you. Be confident and friendly. You have done nothing wrong, there is nothing embarrassing or weird about basic human interaction. Just say something like: "You got a name?" when she answers, introduce yourself and shake her hand. (It is very charming when a guy actually shakes your hand, because it's unusual.) Start a small talk conversation. Be like: So what school do you go to? or if she happens to be doing something like sketching or writing or reading or listening to music, ask her what she's drawing/writing/reading/listening to. Showing an interest in what she's doing makes a big difference. Insist she let's you see it/listen to it. Ask her about it. Go further into the topic of whatever she's doing. Make sure you compliment her on whatever she's doing if it's something like drawing or whatever. Use her name when you speak to her because it adds a degree of personalness to the conversation. If she asks why you're talking to her, don't let it get awkward. Be very confident and comfortable with the fact that you came over to talk to her. Just tell her she looked like a really interesting person. If you want to mention that she's pretty too, that doesn't hurt, but make sure you mainly focus on something other than looks that drew you to her, because most girls want to be worth more (and be noticed for more) than just a pretty face. When you finish the conversation, just come right out and ask: So, you wanna give me your number?
If she has a boyfriend or something or if she just says no, then you just shrug it off, and tell her it was really cool meeting her, and leave on a pleasant note. Just walk away. the bright side being: you never have to see her again, so it doesn't matter.
(another idea could be if you were in line at a starbucks or something and you see an interesting looking girl in front of you, wait until she orders and (as long as she hasn't ordered the entire menu, after all, if it IS starbucks, then if she buys one drink and you pay for it, you're about seven thousand dollars in debt already. seriously, the prices there... yeesh) step up and say: "I'll cover it." To the cashier. Insist on paying then ask if she would mind if you joined her at her table for a couple minutes. It might sound cliché, but it almost never actually happen now, and it really is thoughtful. It's a very charming thing for a guy to do.)
anyway, those are just some ideas if you're looking for a girl to date. Start with her number, text her for like, a week and a half being flirty, then call her (call, don't text, it's so much more personal. but text her first to ask if you can call her for a moment.) and ask her out over the phone. :)
if any guy has advice on how to get a boyfriend, I'd love to hear it, because I am really need a distraction, and I kind of want that distraction to be around my age, male, preferably a Homosapien, and have a cellphone and no girlfriend.