As you get older, asking someone out gets easier. Knowing whether or not they'll say yes, however, stays just as difficult until you die or get married.
I can walk into a room, take a quick glance around, and know who is into whom immediately. But when it comes to whether or not a girl likes me, I am as clueless as a PC user looking at a Mac. And my use of analogies like that doesn't help me with the whole dating thing.
One of the reasons I have such a hard time knowing what someone really thinks of me is the distraction of what I want them to think of me. In high school, I'd make sure to say hi to this one girl as we passed each other in the hall. Usually, she'd smile and keep walking. But one time, she stopped to talk to me, even saying hello first. That had to mean she wanted me, right?
But a bigger reason that I have difficulty grasping whether or not a girl is in to me is because people lie. Many do not lie on purpose; it's a subconscious thing. I have seen many girls flirt with guys simply to get a confidence boost and a few free drinks. These girls have no intention of ever seeing the guy again, but they want to be able to say that they were the ones who turned someone down. Guys occasionally do this, but less often since we'll usually go home with any girl if she says yes.
The reason that asking someone out is so difficult is because we cannot predict their response. There's a comedian named Dustin Chafin who has a bit about how we handled this in elementary school. You'd simply pass a note "I think you're foxy. If you dig me, check the boxy." If we could still do this, life would be much easier. Lamer, sure, but easier.
I once had a long conversation with a female friend to whom I was quite attracted. The subject turned to how a guy could tell if a girl likes him or not. Okay, I outright asked her how a guy could tell if a girl likes him or not. She told me about a few signs laughing a little extra at his jokes, touching him whenever possible, and steering the conversation towards dating or sex. She'd been doing all three of these things all night, so I took a chance and called her on it. She laughed, touched my arm, and told me that I was being ridiculous. After all, these signs didn't count when they happened between friends. And then she asked me about my first sexual experience. In a friendly nature, of course.
We all know how difficult it is to get out of the friend zone, but the "I barely know you zone" doesn't work either. Meeting someone at a bar can be fun, but the possibility that it turns into anything substantial is more uncommon than an English major getting an A in a physics class. Wow I have really got to quit using those analogies.
The easiest way to meet someone is through a friend. But the third party introduction can lead to problems of its own. If you hit it off, you may step on your friend's toes because they might have been after the person they introduced you to. And if it does work out, you better get married. Because if that relationship fails, you'll have to argue for custody over your mutual friend since the three of you can never co-exist again. Don't bother trying there's nothing worse than going out to a bar with an ex. "I'd like to buy a shot of awkward for my friend here. Make it a double."
In the quest to couple off, we are left, then, with one way out being completely inadvertent. Meeting someone accidentally is a wonderful thing, since you have no way of learning most of each other's flaws until a few dates in. And the older you get, the more someone is likely to give at least one date a chance. If they turn you down when you ask them out, that's okay too they weren't in your life before, so what's so much worse about them not being in your life now? As long as you don't ask anyone out over a loudspeaker, rejection is not humiliating because no one has to know it happened. Unless she writes a memo to your friends.
"I thought Steve was gay, so I said no way."
Maybe it's better that we're beyond the whole note thing.