walesmd (reddit.com)

"There are really only two paths here: either you talk to the person and they may like you; or you don't talk to them and it is literally impossible for that person to like you. You are making the decision for that person as to whether they should like you or not; it's you being selfish, thinking only of yourself and not giving another person the opportunity to enjoy being your friend (or whatever it is you are looking for).
When it comes to actually talking to them - it sounds difficult, but don't give a fuck. Really, why should you? You don't care about their opinion, you don't know them! If they kicked you in the nuts and walked off, sure your nuts would be sore for a bit but in a week you wouldn't even be able to remember what they looked like or what made you want to strike up a conversation with them in the first place.
Be confident, be yourself and do not give a fuck. If they don't like you for that, then why would you want to be their friend in the first place?
To be perfectly honest with you, it's difficult. It took separating from my wife for me to realize that I had spent the last 5 years trying to keep someone else happy, to the detriment of my own happiness, and that honestly I don't give a fuck. Don't like me? Don't talk to me. Don't want to see me? Go somewhere else.
Life is too short to mope around like a pussy, scared and all alone.
Here's your homework assignment for tonight:

• Go to a coffee shop - don't like coffee, fuck you, go anyway
• When you approach the counter, genuinely smile at the cashier and ask how their day has been. Don't ask in that "this is what I say when I approach a cashier" way, genuinely ask and genuinely be interested. Their just going to say good or nice anyway, it's not a big deal. You nod your head, smile, and say something like "good - I'm glad your having a good day."
• Now you order your drink, if it's one of those places that writes your name on the cup, come up with something funny. "Robe and wizard hat" or "reddit, that's r-e-d-d-i-t" - it doesn't matter, you are just trying to break your same old lame-ass pattern here.
• As you are waiting for your drink, find someone also waiting that doesn't seem uptight/pretentious/caught up in their own shit. "So, what'd you order? I never know what to get..."
• Take this opportunity to scope out the room, is someone reading a book you've read? Someone have the same shoes as you? Same laptop? A cat sitting on their head? Find someone on your path out the door.
• As you walk past that person, with your drink in hand, make your comment. "You look nice/I like those shoes/My cat does the same thing" then you walk out the front door LIKE A BOSS.

Do shit like this everywhere you go. If someone makes eye contact with you, don't look away - SMILE and say hi to them, ask them how their day is going, whatever. People like human interaction - we crave it and need it.
As you do this more and more, you will naturally become more confident and you will find yourself talking to more people and meeting awesome people without even trying. You'll lose this nervousness and lack of confidence naturally. Start small and continue doing it. Don't let a single day go by without smiling at 10 random people and saying hi to each of them and try and start a legitimate conversation with at least 1 random person (elevators are good for this, anywhere there is that awkward moment where you don't know what to do).
Humor works wonders - even if it's stupid humor. Someone walking past with an iPod, start dancing next to them, then go for the high-five - it just doesn't fucking matter man. 95% of the time you will never see these people again in your life and if you do, they'll remember you, which is what you want!"