So, there is this girl I like in school, but I barley know her, just talked to her once.

And I want to invite her on a date.

I'm normally shy about that, but I guess I have to try it.
Do you guys have any plans like that, a first-encounter on this evil day?

This is coming from someone who was a shy guy in high school, so I totally understand that the advice I'm going to give can sometimes be easier said than done...

But really, the best approach is the direct approach.

Don't under-do it. If you just walk up to her and say "Wanna go out?" she'll be confused (especially if you guys don't know each other that well)

But don't over-do it either. I've seen guys (and hell, I've done it a few times myself) who basically start blubbering about how gorgeous the girl is and how they think it could be love and...eh, you can guess why that can blow up on you.

A while back, there was this cute girl who worked at Borders Bookstore who I'd see whenever I went shopping there. I only knew a few things about her: her name and that we both liked The Dresden Files. When the store was closing and I was shopping there for the final time, I walked up to her and basically told her straight "I know we don't really know each other, but the store is closing, I may never see you again. Do you wanna grab coffee sometime?"

...That story ends with the ever so awkward "I'm actually seeing someone right now." line, and hey, that happens. You move on.

TL;DR version: Just find a good chance to talk to her (preferably isolated from her friends) and just be like "I know we haven't talked much, but you seem cool, I'd like to get to know you better. Would you like to maybe go out sometime?"

Women appreciate the direct approach, and it's entirely possible she'll say No (for whatever reason) but by just taking the leap and asking her out, she'll respect that, you'll feel better no matter what, and you won't have any regrets.

Good luck, man.

Uh... I have plans, but it's not a first encounter.

I'm calling up the geeee-efff and singing some love songs she likes into her answering machine. Then I'm gonna go down and surprise her, bringing chocolates and all that jazz. Then taking her out dancing.

As has been said, be direct. Also, do so as soon as possible; time is short before this holiday I've been hearing about.

RAKtheUndead:
Here's what you do: You sidle up to her awkwardly and start talking loudly about computers or cars or a subject like that. Bonus points for additional obscurity. She'll be so overawed at your knowledge that she'll jump into bed with you at the soonest opportunity.

Worked for me, thanks RAKtheUndead your the greatest!

Maybe don't place so much faith in having this done on Valentines Day, who cares if you don't manage to get it done for this holiday. Don't set arbitrary deadlines for yourself, it is a good way to get worked up and psyche yourself out. By all means, go for it but if it doesn't pan out, hold off till the weekend or something, good luck!

Well first you need to watch them from afar
then when the time is right, you make your move
Chloroform will normally be right

Hold a handkerchief to her face saying: does this smell like chloroform? Applying chloroform to the handkerchief beforehand is optional.

Eh, how much did you talk on your first introduction to her, and how long ago was it? If you had a lengthy sort of chat, like 5-10 minutes at least and it was fairly recent, within the past week, I think you've got a good enough basis to ask her out.

Anyway, just talk to her some more, find an excuse to have a conversation with her. At the tail end of the conversation with something casual like, "So what are you doing for Valentine's?", it's passive but it lets her know exactly what's coming. She can answer whichever way she wants, if she doesn't want to go out with you, she will make something up such as, "Oh I'm going with my friends to X", basically something to imply she's booked for the day. If she is at least partially interested she should leave herself open such as , "oh I dunno".

Anyway, sense for the moment, if you feel she's left an opening for you, go ahead and pop the question. Except you NEVER ask for a date, girl's want a man who is dominant. The invitation for a date should be phrased in a manner such as, "we should go do X together". This is a great way to do it since it's also very passive, though it's clearly a date implied, it's passive enough that she's not being put on the spot, she can freely answer in whichever way she wants.

Also try and avoid talking to her when friends are nearby, girls HATE being put on the spot like that with others watching. If you have to, get her number and do it via text. Or you could have a conversation with friends present, and leave it at that, then try and snipe in the proposal later in the day when she's unattended.

They key thing is you need to feel the moment, girls are incredibly expressive, talk to her and keep your eyes split for positive reactions. Be dominant and yet try to phrase everything as passively as you can. A passive mood implies a non-urgent situation, and a lack of desperation, you're indifferent towards the outcome.

The most important thing though, is confidence, girls hate feeble men, and if you sound scared or nervous when approaching her, your chances are going to be much lower. Pump yourself up before approaching her, you are the fucking man, tell yourself that over and over, you're a beast, a god damn stud, and every pretty lady would be blessed to have a shag with you.

Confidence and dominance are the main reason why it's commonly insinuated that nice guys never get the girl, and that it's always the douchebag who gets her. This is because douchebags typically act dominant and confident while nice guys typically act submissive and perhaps with a lack of confidence. This doesn't mean you need to act like a dickhole, but to get the girl you need to show some balls.

EDIT:

Also try and get some info on her beforehand, try and find her Facebook page or something, look for things such as relationship status. Or just be straight with it and ask somebody who knows her better if she has a boyfriend. With Facebook you could also possibly find some potential conversation points to help things flow a little more smoothly while building up to the proposal. Though don't do something stupid like notice her favourite movie is Casablanca, "Hey do you like Casablanca? I love Casablanca, best movie ever." Makes it kind of obvious what you've been doing.

I'm not sure a first date on Valentine's Day is a good idea, it is too emotionally charged of a holiday and she might think it is cheesy.

My thoughts on V-day:

RAKtheUndead:
Here's what you do: You sidle up to her awkwardly and start talking loudly about computers or cars or a subject like that. Bonus points for additional obscurity. She'll be so overawed at your knowledge that she'll jump into bed with you at the soonest opportunity.

You should really start up an advice blog, or at least run a "Dear Abbey" type of column on the Escapist

Just do it man, that's what valentines day is for right?

Good luck!
I don't have too much else to say really.
You seem to have a plan already so just...
Good Luck!

You ask her out for the 15th! That way, you have the romantic 14th crap lingering in her mind, but it isnt actually Valentines.
Plus, that throws her off her guard, and might make her more open.

TrilbyWill:
You ask her out for the 15th! That way, you have the romantic 14th crap lingering in her mind, but it isnt actually Valentines.
Plus, that throws her off her guard, and might make her more open.

And if she shoots you out of the saddle, half-price candy at the supermart to drown your sorrows in.

Lionsfan:

RAKtheUndead:
Here's what you do: You sidle up to her awkwardly and start talking loudly about computers or cars or a subject like that. Bonus points for additional obscurity. She'll be so overawed at your knowledge that she'll jump into bed with you at the soonest opportunity.

You should really start up an advice blog, or at least run a "Dear Abbey" type of column on the Escapist

I second this.

OT: i have very little experience in this field, but from what little i do know (read: what great volumes i read on the internet), i'd say just go for it, act normal. If she declines, fuck it, move on.