Well one, time I was at the laundromat, talked to this random girl (it was just us in there), the topic shifted over to games, turns out she was a Dwarf Fortress player, with a bay12 account, no less, though she's a lurker. So yeah, go for it, since you never know.
The problem then becomes "how do I start a conversation with a random person I know nothing about".
I guess I could just ask questions and get to know them but that only works if the person I'm talking to wants to talk to me and is willing to talk to me, a random stranger they don't know, about themselves.
Ah don't worry about it Spehss. Let me tell you, I got a girl's phone number recently... I know, right?... but then she just ignores me when I text her. So I'm like "Ah, snubbed again!" as I trash that number and go about my week, only kinda disappointed. The moral of the story is that this pessimistic second-guessing of yourself is not only deluded egocentric behavior, I would argue it's demeaning towards this hypothetical girl. That is to say, that presuming to know what someone else is thinking or feeling is arrogant and belittling to the other person, because hey, you don't need to talk to them, you have their whole thought pattern already mapped out.
Now, you might think "Naw Josh, I'm just afraid of rejection, and that speaking to her is just inviting that rejection that will finalize the negative beliefs I have about myself!" and I'm saying that that negativism is itself a delusion of grandeur. One can't truly know the future, or what is happening in anyone's head, the loosest presumption of such reveals that you don't know what you're talking about.
I don't like giving advice Spehss, I think the problems of everyone here are too complex for any anonymous stranger to mend in even the slightest way, and that assuming that I can is simply the height of arrogance, but I'm in a rare good mood so here's what I say: Just let her reject you. If you're so certain that she'll find you intrusive, unattractive, creepy, or (and this is the one that kills people) so uninteresting as to be unworthy of conversation, then just let her reject you so you can regain this little bit of agency and certainty in life, cause that WILL make you happy, even if the rejection hurts. That you agonize over talking to this girl, she is inflicting unhappiness on you without her even knowing it, she has so much control over the emotional state of someone she has never spoken to! But by you coming forward, and giving her that chance to reject you, why, both parties involved finally have closure, it's the finality of actually performing the experiment rather than simply allowing the hypothesis to languish in your mind where it can remain uncertain forever. It's that uncertainty and feeling of having no control in your life that is making you unhappy for certain, everything else you think is making you unhappy is in fact illusory, and regaining control and certainty, even through a negative outcome, definitely will improve your outlook on life.
The short version: You don't need a woman to make you happy, you just need your balls back, and you have to go get those yourself.
And if she doesn't reject you? Afraid I can't help you there, if you've read my posts, you know that's unexplored territory for me!