This guy is a freakin' Dungeon Master.
Striking up a conversation
So, you walk into a bar a Neutral Grounds, and you scope out this not-so-weird-looking guy with a stack of Magic: The Gathering cards in one hand and a Coke in the other. You think to yourself "I need to talk to that slightly overweight man." The obvious approach here is to talk about MTG, and that wouldn't be a bad idea, but the dude's already in there, playing the game. The dumbest thing to say would be "Hey, you like Magic, too, huh?" No shit, Sherlock. You're on the right track, though.
Take a protip: Notice other things about him. Geeks can be very expressive about their geekeries, one way or another. Maybe he's got a Captain America shirt on, or a Gunblade keychain on his bag? Use those to strike up a conversation. Shows you really know your stuff and that you notice the little things. It's important you start with a topic that they're comfortable with. Otherwise, especially if you're halfway attractive, all you'll hear is "ffffpppttt gggrrrraaabbbuuu wwwaaahhh?"
Section II: Snagging
The First Date
A common misconception is that when you wanna date a geek, you have to do geeky things all the time. "Oh, I'm going to date a geek! We have to watch Tron or The Hobbit!" While it would be fantastic if you were really into it, that's not necessarily true. They're human beings, too. Sure, they may be a little weird, but that doesn't mean they don't enjoy doing normal human being things. Have coffee, go bowling or watch Twilight or something equally inane.
Letting them know you're interested
Many of the geeky are remarkably socially inept. I'd say about 95% of them seem like they suffer from some sort of learning disability when confronted with pretty girl. More often than not, they will NOT understand any hints you drop so you should just forget about subtlety. Just tell them straight up.
If you still insist on doing hints, though, you have to speak their language. Here are a few examples.
- Did you know that Excelsior means "even higher?" Let's see what else we can get Excelsior.
- I have a triforce I really want you to see.
- CGC says 9.3 but you're a 10 to me.
- Would you please check if I'm super-articulated? or I want to show you all my points of articulation. (Say this to toy geeks. They'll get it, trust me.)
- I'm like Reddit. I always go down.
- We need to check if our ports are compatible.
- Wanna come back to my 127.0.0.1? I'll give you full access.
I know other things we can do co-op.
You get the idea.
Dating
For conversation, just speak as if you would on a normal date - with ridiculous amounts of awkwardness and extended periods of silence. Geeky topics are appreciated but are not necessary. In fact, pop culture references, when overdone, just become plain insulting. Saying "May the Force be with you" every time you hang up or say goodbye may be cute at first but will get old really fast.
It is very, very appreciated if you make some effort to learn the things your little geek obsesses over. You don't have to have encyclopedic knowledge of it, just the fact that you took five minutes to read a Wiki article about it is enough. However, when they do make a reference and you don't get it, please, please, never pretend to understand, smile wryly and then giggle. They can see through that. Just say you didn't get it and they'll explain it to, lengthily.
Section III: Keeping
Respect the rules
Geeks are rabid when it comes to their rules about their possessions. This is stereotypical of someone who may be considered a geek, but this is as close to the truth as a stereotype can get.
If your geek has a bunch of comic books boxed, bagged and boarded, it is automatically understood that you are to stay at least 10 feet away from them at all times. Under no circumstance is it okay to "sneak a peek" or "check it out." A crease on a comic book seriously feels like a stroke. Only with his explicit written permission can you touch his stash, and that's provided you handle the comics with the proper care they deserve; rest the comic book directly on its spine upon your palm and turn the page at the center and not the corner. Never the corner.
The rule above applies to toys in glass cases, movies stacked upon a book case, games arranged upon cabinet, any kind of electronics that look like they shouldn't get wet or dirty, and especially for pieces that are actually displayed on the walls. Do not touch them.
Seriously, this means Off Limits, Keep Away.
Refrain from telling them how to spend their money
Geekery isn't cheap, and it is almost always materialistic and driven purely by commercialism. This is what makes them who they are, though. Unless it's getting way out of hand, friendly advice may be better than outright telling them to "stop buying that kiddie crap." If they're decent human beings, they'll understand. It's just hard for them to see it the way you do, so you're gonna have to guide them there a little.
Here's a conversation you want to avoid.
Girl: You already have 350 freaking Pokémon cards! Do you really NEED to buy a dozen more?!
Boy: It's over. Sorry, but Pikachu, I choose you.
I mean, who wouldn't? Am I right?
Don't demean their interests
To you, they're toys; to him, they're collectibles. To you, they're video games; to him, they're interactive multimedia experiences. To you, they're comic books; to him, they're... well, comic books. Point is, these things mean a lot to him and it wouldn't do anyone any favors if you trivialize that. You could at least pretend to care about them.
Small gestures
Another big misconception about geeks is that the only way to make them really happy is to get them the top of the line stuff, like an Alienware laptop or a Bowen statue. Like any other person, grand gestures make them ridiculously happy and very grateful but what they really appreciate are the small ones. I can personally attest to this. Give him a pair of Iron Man cufflinks, or Green Lantern boxers. Those are more than enough. If he really wants something, not even the wrath of a woman scorn can stop him from buying it.
Section IV: In Conclusion
So, it seems like getting yourself your very own geek is a ton of work. Yeah, it is. It's like caring for a mildly retarded monkey that smells a little worse or a cat fixated on a laser pointer but not as cute. In return, though, you'll have someone who will treat your relationship like a great adventure or epic campaign. He will see your parents as the final boss to be conquered to win your hand. He will be fiercely loyal and protect you like everyday was an escort mission. You will be the Princess Peach to his Mario, the Zelda to his Link, the Jean Grey to his Cyclops, the Rinoa to his Squall, the Robin to his Batman.