Yes, I does happen. It did to me and it did to others. I think you are right as well: A lot of things in life need planning and good execution. But there's another very important ingredient: opportunities.
You go to a bar to meet new people. That's a good plan to create opportunities.[1] But there are a lot of opportunities when you are not looking for them. And when you are not expecting these they can be very hard to notice. I think that's the point of not planning: Not a anarchistic approach to life but going into the world with open eyes.
I leave you with a bit of science: A bunch of poeple are asked to rate themselfes how 'lucky' they are.
"I gave both lucky and unlucky people a newspaper, and asked them to look through it and tell me how many photographs were inside. On average, the unlucky people took about two minutes to count the photographs, whereas the lucky people took just seconds. Why? Because the second page of the newspaper contained the message: "Stop counting. There are 43 photographs in this newspaper." This message took up half of the page and was written in type that was more than 2in high. It was staring everyone straight in the face, but the unlucky people tended to miss it and the lucky people tended to spot it."
[1] That may be something you'd want to fix about yourself. Just like anything else, you can learn to be socially skilled. The basics are not seeming miserable (who wants to talk to a miserable person?), engaging people, making people feel good about themselves, not complaining, and reflecting all this in body language.
Just like anything else, practice is all it takes. If I were you, I might read some stuff about pickup - because the best way to pick up a girl is to be socially skilled. Those guys have definitely done a lot of research in that arena. Unfortunately it can be a very seedy industry. There was this great article I was going to show you about social vibing, something that was kind of an epiphany for me, but the site (bristollair) seems to have sold its soul.
Basically, the point is you want to be an upper, not a downer.
Also, forgot the biggest shortcut for social skills: smiling! Try to trick yourself into thinking of something that makes you happy/something really funny that makes you laugh inside instead of just moving your muscles. People want to be around happy people!
You go to a bar to meet new people. That's a good plan to create opportunities.[1] But there are a lot of opportunities when you are not looking for them. And when you are not expecting these they can be very hard to notice. I think that's the point of not planning: Not a anarchistic approach to life but going into the world with open eyes.
I leave you with a bit of science: A bunch of poeple are asked to rate themselfes how 'lucky' they are.
"I gave both lucky and unlucky people a newspaper, and asked them to look through it and tell me how many photographs were inside. On average, the unlucky people took about two minutes to count the photographs, whereas the lucky people took just seconds. Why? Because the second page of the newspaper contained the message: "Stop counting. There are 43 photographs in this newspaper." This message took up half of the page and was written in type that was more than 2in high. It was staring everyone straight in the face, but the unlucky people tended to miss it and the lucky people tended to spot it."
http://www.telegraph.co.uk/technology/3304496/Be-lucky-its-a...
[1] Well, that's the clichée at least. For me, this is not such a great plan, as I'm too socially awkward... :/