WrongSprite said:
Movies are suicide, you want to actually be able to talk to her.
Seconded, at a date you are meant to be able to show your personality. At a movie, you are essentially sitting silently next to each other, all attention put on an outside source, no eye contact or interaction. No real opertunities for escalation (because the whole puttting your arm round her thing is stupid). Recipe for awkwardness.
Whatever your date is, make sure that its easy to touch her. Not in a creepy way obviously. If you are going out for a coffee, sit beside her not opposite, maybe avoid dinner. Go to the park or something.
The reason for this is that you want to escalate to build attraction, or else you will be left in the friend zone. Escalation just means taking it to the next level, but this can be on a very small scale. Touch them on the arm frequently (but not for a creepy length of time), if you are crossing a road, hold their hand. As the date progresses, just keep building up. Touch their face, hair, stomach, lower back, hug them, high five them, tickle them, whatever seems appropriate.
This will work if AND ONLY IF you don't come off as creepy, and the best way to do this is have a playful vibe about yourself. Alternatively, make the touches very brief and have no "value", ie. if you are going to touch them on the arm, don't look at your hand, don't let it linger, make it seem natural etc.
THE REASON FOR THIS: When you finally want to "seal the deal" (ie. go in for a kiss), you want her to be comfortable with you touching her. If going in for the kiss is the first time you are really getting close, then it will come off as being wierd. The whole point of escalation is that it gives a natural progression.
Digi7 said:
Okay, MASTACHIEFPWN...
Just by your username and the fact you are participating in a Left for Dead 2 tournament are enough for me to assume you're a bit of a dork.
However, cuteness ALWAYS wins over being a confident badass in any girl's books whos worth being with. Don't get me wrong, be confident, but not a jerk. Be romantic, kind, funny and sensitive. If you have wanted her for this long just tell her that, it will make her feel special. Make sure you look good on the day you ask her. Shave, cut and wash your hair, wear nice clothes and smell nice. Don't stutter or fidget. Just relax.
Take it easy, don't seem to eager, it will put her off. Just ask softly, preferably just as you part. It's easier on the both of you. If she wants to say no, or wants to think about it, she has time to come up with an answer. It is NEVER fair to put someone on the spot, and she may say something she doesn't really want, which will make it harder for both of you.
Which brings me to my next point: There is NO point in having a relationship that one of you does not want. Don't labour the point.
If you have liked this girl for this long you are obviously very emotionally attached to her. Don't let yourself be crushed if she says no. Accept it, learn to let it pass, and move on.
And my most IMPORTANT TIP:
ALWAYS BECOME EMOTIONALLY ATTACHED TO A GIRL BEFORE YOU ASK HER OUT.
Girls are very emotionally driven beings. First off, are you even friends with this girl? If not, forget about it, or at least hang out for a while first and get to know each other. If you are, what's the tone of your relationship? Can you identify that?
Good luck anyway, mate.
Some of this is ok advice but one thing I would say would be: How often (rom coms not witstanding) do you see the girl dating the confident badass while the "cute" guy sits on the sidelines pining about why this girl only dates douchebags when he would be so much better for her?
This is not to say "be a douchebag", but douchebags do often possess certain qualities that are attractive to women: confidence, spontaneity, humor, social proof (ie. large circle of friends). Similarly, guys attempting to be "cute" often mistake bad qualities (awkwardness, a submissive attritude, fear of escalation) for good ones. They will essentially make themselves, at best, the gay best friend, or anything from the best-friend-that-fancies-you to the lapdog. However, some of the qualites are positive, girls do like nice guys. However, its a very particularl kind of nice. The nice that you would be to your best friend, not the nice that you would be if you met the Queen/President.
The answer is to have the best of both worlds. Be confident, spontaneous and funny, but also have the good kind of nice, try and build an emotional connection.