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[Tiruin]

...

Anyway. Try to note yourself in the situation which you plan to do. Imagine how would it be if you were instead the recipient of your action rather than the doer-reverse roles and all that and look at it from there, if that would help.

Any update on your part Akura?

[Osmosis Jones]

Maybe a little late here... but whatever you do, don't go all creeper on her. Don't try and meet her at work, don't write letters professing your undying love, and for god sake don't send her a creepy pm on FB asking her to go out. You have to understand that doing all of those things are very fast ways to make her uncomfortable.

Spoiler: Spoilering for length (click to show/hide)

Imagine how you would feel if a 50-year old guy (yes, an older man; it's the closest we can get to replicating the gender dynamic here) started following you around and offering to take you to the movies. Chances are, it would make you rather uncomfortable, yes?

Even leaving aside the awkwardness of being propositioned by a stranger, you have to understand that gender roles play a very large role in our interactions. As a rule, us guys are bigger and stronger than girls; that immediately means that if anything goes wrong, a girl is at a disadvantage, and is sadly something most girls are forced to be aware of their entire lives. Having a strange guy saying how much he loves you is going to be raising a lot of red flags, and honestly, any sensible girl is going to nope the hell out of there.

So... what do you do?

Listen to Shadowgandor and Vector, they've given you some good advice; meet the girl at a party or outing with mutual friends. Ideally, get the mutual friends to directly introduce you. What you have then is a situation where:

a) You have a reason to approach her; you're no longer some random creep, you're so-and-so's friend from high school. It means there's an icebreaker for the conversation (which makes things easier, and you'll look better for it), and your friendship with the mutual friend is implicit support for your moral character.

b) She's not alone/at a power disadvantage; she's going to be with friends, and she knows she'll be able to say no without repercussions. While that sounds bad, it's not; knowing you have an option to do something is not the same as wanting to do it, and knowing that there is a safe out along the way will actually make her more likely to talk to you. Using an analogy to think about this; you wouldn't walk across a 10cm wide beam strung between the 50th floors of 2 buildings... but you'd happily try and balance on the concrete curb at the edge of the street. They're the same width, but if you fall off the curb, you can safely land on your feet.

c) Parties are social lubricant. People are happy, and more outgoing at a party than they would be in day-to-day life. Unlike talking to her at work (where she may be stressed out, under the hammer, and tired), she will be in the mood to have fun and meet new people. Sometimes, there may be liquid assistance as well... while I'm not advocating getting either you or her drunk, one drink may help you and her relax, and chat more freely.

That said, when you do get the chance to meet her in a comfortable setting... don't be afraid. You do have to be able to go up to a girl and chat. Make her laugh, smile, etc. If you keep sitting in the corner trying to catch her eye, you won't be romantic, you'll be creepy. Don't ask for her number straight away, but if you've been talking for a good half hour or so, asking for her FB details is generally okay. I think it's maybe because it's become a bit of a cliche, but asking for a girl's number has a very clear meaning, and doing that early on may make you come across as a bit of a sleaze.
If you've set on the number though, a good way to ask for it is to find some common interest, and talk about making plans later; I've had good luck with something like this "Ohhh, you like hiking too? A few of my friends go every few weeks... tell you what, give me your number and I'll shoot you a text the next time we are thinking of going."

Finally, if all this sounds hard... sorry bucko, thems the breaks. Romance isn't easy. Fun yes, exciting certainly, but never easy. You do have to be willing to put yourself out on a limb, and you do have to be prepared for rejection.

Good luck!

[DJ]

"Accidentally" meeting at a party seems a lot more creepy to me than the direct approach. I don't really see what's creepy about sending her a message on FB along the lines of "I've noticed you around, you're really cute. Wanna get coffee sometimes?". It only gets creepy if you keep pushing it in case of negative reply or no reply.

[Osmosis Jones]

I'm not saying "accidentally" meet, I'm saying just regularly meet. Ideally, he gets his friend to introduce them, but at the very least, be in a situation where he has a legitimate reason to talk to her.

Ask a pretty girl sometime how many messages like that she gets. From the few friends that I have asked (yes, anecdotes are not data, but still), it's a lot, and they generally respond with a block. Sometimes they tell them to piss off first.
Either way, I don't think it sets a good tone for starting a relationship with a girl Akura says he loves. Asking a girl out for coffee over facebook pretty much purely says you only know her by physical appearance, and from that, there's only one assumed motive.

Meeting someone at a party/on a road trip/at the movies/whatever it is you do with your friends means there is some other reason than just physical attraction driving the interaction, and if Akura truly wants a real relationship with a girl, it's better to let things develop over a few days than starting things straight up with a coffee shop date, and all that entails.

EDIT: Basically, he should aim to make her his friend first, and then try and become her boyfriend if he still likes her once he knows her. The "friendzone" is a bullshit phrase used by people who don't understand how relationships work, and becoming someone's friend is not some terrible fate.

[DJ]

Well he *doesn't* know her, so pretending that he approached her because of her personality is just dishonest.

[weenog]

I wouldn't go so far as to say that.  He knows a little of her, which is not sufficient to start a relationship, but certainly enough to legitimately pique someone's interest.  Dick waving on facebook isn't brutal honesty, it's abject stupidity.

He could always -- once he's worked out a sane context in which to start a conversation -- point out the facets that interest him, and ask her about those.  It would help fill in the blanks in what little he knows of her personality, and demonstrate his interest at the same time.

[Caz]

Let me tell you a story.

Once upon a time there was a beautiful girl, who grew up in a society where it was expected that she be feminine, and let guys approach her. There was a boy she liked, but she'd spent an entire lifetime being told not to talk to strangers, not to go out alone after dark, and to stand around and wait for boys to ask her to dances and that it was improper for her to be the one to approach boys.

But she liked this one particular boy. So, she smiled at him in an attempt to get his attention and clearly communicate that she definitely had noticed him, and that she'd be receptive to him approaching her.

Unfortunately, the boy was too concerned about how she might react if he approached her, so he sat around and stressed about it, asked a bunch of people online who all said to talk to her. But he never overcame his fear, so he grew up to be lonely, alone and miserable, all while watching from the shadows, running and hiding every time a girl smiled at him, complaining constantly about how girls like guys who treat them badly, and how well he'd treat them if only they'd give him the chance. She grew up also lonely and alone until one day one of those "bad guys" actually had the balls to talk to her. Relieved to FINALLY have somebody approach her, she became his girlfriend, promptly got pregnant, then was abandoned. Overcome with grief, she gave her child up for adoption and threw herself off a bridge where she landed on a bunch of jagged rocks, shattering her legs and slowly died an agonizing death over several days, all while wishing that one boy she'd smiled at had simply spoken up.

The end.

Wow. You really do paint a picture.

[Parsely]

Go say hi you silly. Everyone's trying to turn this into a philosophical thing.

[Akura]

Talk to her.

Biggest problem isn't working up the willpower to talk to her. It's actually finding her, in situation where I can strike up a conversation with her. Hell, I'm not even seeing her just in passing anymore, though I've been assured she's still around.

I wouldn't go so far as to say that.  He knows a little of her, which is not sufficient to start a relationship, but certainly enough to legitimately pique someone's interest.  Dick waving on facebook isn't brutal honesty, it's abject stupidity.

I also hate Facebook and will never use it. I wouldn't call any relationship maintained through Facebook an actual relationship. Plus, I don't think she has a FB page.

[DarkArtemisFowl]

Take your time then. Just wait and see if you can have an opportunity to say "hello".
And of course, be a gentleman and all that jazz. Manners count a lot in my opinion.

[QuakeIV]

Gentlemanlyness can make you look way better than you might think, especially in the heat of the moment.

[gman8181]

What everyone else said. Worse case scenario you get rejected and move on. LordBucket's post is a rather extreme example but it also helps get across something an of an important part.

That said, I know it can be hard. Even rationalizing things, you still feel nervous and worried because that's what your mind and the chemicals in your body are making you feel. It might help to try and change your perspective on things, so I'm going to try and put in my own little bit of advice / analogy.

Everything is sort of relative. What you find attractive and what another guy finds attractive can vary dramatically. Does that mean any one of you have an opinion of less worth? No. Maybe most people find certain features to be attractive and thus those types of features are deemed by the majority to be "attractive" but technically that's not any more true than saying just because a large amount of people like pizza, it's a superior food compared to peanuts.

So what if she doesn't want to go out? It's not a huge deal if you get turned down. It's okay because someone else out there will like peanuts you and that person is out there somewhere. If you don't ask you'll never get your pizza chance with her and if you do, you'll either get what you want or find that you need to move on and keep looking for better foods that mix well with you.

Well that analogy got a little out of hand but I hope the point got across.

Edit: Oh and how could I have forgotten the importance of personality and humor. Those things are like the yummy spices on top of food. Or maybe they're the food and the looks are the spices. Or maybe one's the food and the other's the drink going alongside it...

Er the point is that make sure you actually like her personality not just her other... "features". That stuff is really important otherwise your relationship is much more likely doomed to a short term sexual affair. Anyway humor and personality can really make a big difference. I've found often that people who may not have been drawn to me by my looks alone can often be tipped over by some funny jokes and shared interests.

Edit2: Whoops, how could I have missed this,
"Biggest problem isn't working up the willpower to talk to her. It's actually finding her, in situation where I can strike up a conversation with her. Hell, I'm not even seeing her just in passing anymore, though I've been assured she's still around."

Uh... Yeah I don't know. If that's the biggest problem just ask someone who she's friends with where you might find her.

[Akura]

Goddamn it, I'm pathetic. I actually had an oppurtunity to ask to have lunch with her, but I couldn't say anything. In my own admittedly weak defense, I was having a pretty crappy day week up to that point and wasn't in the mood to talk to anyone, especially on the spot like that.

The good news is, I have been seeing her order lunch in the cafeteria lately, so it's not like that was the last chance or anything(I hope). The bad news is, I've also seen her leave before my lunch break, so either I'd have to ask her to wait a bit, or try to swing an early break.

[Vector]

Don't worry about it.  If you were in a bad mood, it was definitely the right thing not to try then.  You'll have other chances!

[Akura]

Bad news, good news. Bad news, no encounters this week, and I really wanted to see her(see below).

Good news, I've been assured by a friend of hers that if I were to ask her, she would "almost certainly not say 'no'" and that I should definitely go for it, and the fox's grin they had when they said it might as well have been saying "she likes you too". At the least, it gave me the drive to get through a few difficult days at work.

On a somewhat seperate note, I found one or two desserty recipies I'd like to try. Would it seem wierd if I were to give her something I bake(assuming it turns out well)? It's not something big, something like homeade candy bars. I've bought her cookies before, though I had to give them to her through a third party, she apparently took them well.