First: This deservse a solid response.

You must never give up. Having said that: Give Up, Conor.

How did that make you feel? Pretty damn low I hope. That's because you don't want to give up, and I don't mean what I just said at all. But that poked something deep inside you, because some of us have come to admire, nay, envy, your will-power and drive. I'll stroke you ego latter though ;) I too have a bitching hard time finding my testicles when it comes to asking the girl I've been looking at for the last few months during class, out on a date. Haven't pissed my pants just yet, but you know when you're ready to cream them when you see a really hot girl walk by, well I've come about that close to pissing myself instead in such cases. I have no balls. The ones I grew this year, I was nursing in my basement under a heat lamp since I turned 13. Sometimes I'd take them out into the real world so they'd know what they'd be facing one day. My balls were last seen skyrocketing who the hell knows where as I was confronted with a dire situation exactly one week ago.

There's someone I work with. She's an "older woman" which means "men" who are younger, shouldn't have a prayer at getting a date. I have a theory on that. Women go for older guys because women are more intelligent than men, and lack the crucially mis-leading Mr.Winkie compass. My theory, where if N represents the number of "men" in a room, their intelligence can be calculated thus (ps: I hate math):
-1
---
-N
If you're some 20-year old young "man", would you seriously think you could get a date with a 24-year old woman. Not unless your balls were so big they had to be detached and carried in your backpack so you could walk. What I got last week was a Friday-night date with her, and some of our co-workers. Obviously it isn't anything serious, not by far. It's a friendship date. We don't intend it to be anything more for many good reasons, one of which being that I'm moving, and another being she's recently divorced and neither one of us wants to consider a serious relationship; more like: company. However you look at it, we still went on a "date". However, that starting route is the same; the Y-divider comes later. Let's take a little look at this before I continue (look, I said I was ranting, believe me next time and we'll save a lot of pentup excitement).

Whether I want to be someone's friend, or I'd really really like to get to know them better, it all starts with spending time elsewhere, anywhere BUT where you regularly meet. That shows at least a miniscule amount of effort taken on both sides. Before you get there, talk about things you're both interested in. I know, I've jumped the gun already: How the heck do you find out what she's interested in if you haven't talke to her yet? Well, you don't. So I've ranted my way to the core of your concern. I won't dodge the bullet any more. Try this:

Go up to a total stranger that you don't want to date necessarily... and ask them something innocent: "What conditioner do you use?"
Right off the bat, you're going to know something about her, and I'm not talking about conditioner. You're going to know something about herself no less. You'll know how she reacts to strangers. You'll know how much she's willing to converse with someone. You'll know if she gives a fast answer like it's nothing big, or if she's reaching for her mace. She might be inquisitive and ask you back, why? If she say. How she does, should be noted too. Every word she chooses represents her. If she asks it, short, one-word, or if she's confident enough to get defensive and add explitives, etc. You don't have to, but you can think about it.

What will asking this total stranger a question you aren't really interested in having answered? Experience. If you're going to go in for the kill, train to go in for the kill. You, will have just asked a her a question, and the race is on. Sometimes, the woman is upfront and strong too. Take my last "date". She hadn't seen The Lord of the Rings yet. My jaw dropped. I told her she HAD to see it. She said she didn't have a car. I said I'd drive her. She asked me what I was doing the next night, I had no plans. Then her next "excuse" was that I'd have to pick her up and drop her off. I said it wouldn't be a problem and then asked if it mattered where.

Bing. Let's be stupid and analyse this even though at the time I was playing it by ear with no strategy in mind.

1) You don't know this, but I interrupted her.
You could say I was rude, but I haven't ANY experience in starting a conversation with a girl I wouldn't mind going out with for a date. I listened in to what she was talking about until they hit on something I could talk about. I've been in touch with my feminine side. If they'd talked about their nails or nicks while shaving their legs, I could have jumped in too but ... you know, let's not go there. Onward!

2) She made the first move, but it was subtle, and simple which means even a "man" could dance to that beat.
She gave me a reason why she hadn't gone: didn't have a car. You simply MUST follow up on what ever the reply is. If I take her reply at face value, then if she had a car, she might go see the movie. One simple thing at a time. Here's the big play:

3) I could drive you
Ta-dah, you've asked a girl out on a date. Congratulations. She picked up on this too: remember guys, women are intelligent, something like that comes to them naturally... yes, be afraid, be very afraid, but smile the whole time.

There's no need to analyse further, the games have begun. But what if it isn't so easy like that...

Another scenario

There's another girl I used to know, Sharon. Hadn't seen her in 6 years. I heard she's single and still cute as could be. How the heck could I find out where she was in town and what she's up too? Research. I call friends I know, talk the talk with them, and ask if they'd be interested in having a reuinion from high school, so to speak. And if they've kept in touch with Sharon, or have her number, or email, or pictures of her house so I can go driving around and find out where she lives. Seriously though. Take the ALL-or-NOTHING attitude. Give it all you've got. I talked to my friend Grace, who did have Sharon's number. So I gave her a call and started by saying she probably wouldn't remember me, but it was Morgan Wildman from high school. Chatted about where she'd been these last several years, and let her know why I was calling. You have to call her later to finish off some details. Whether you really do have some finishing details or not. This means you get to talk to her again, like it wasn't a fluke. It wasn't, you planned it. Find out what she does, if she's got a day or night job. Suggest you go out for coffee before the get together and have a catch-up then too. Actually, she suggested that. See, that's all it takes. SOMEONE making the suggestion. However, let's look at your boat.

The Finale: because this Rant has avoided the real issue for far too long already!

You've said boo to her. Which in Winnipeg terms means: nothing. I say this because you haven't been able to continue a conversation with her on a regular basis. This is no insult to you, do not take hurt to what I've just said or I'll beat your ass down! I mean... OKay, here's my take:

The two of you take up the majority of the row you sit in. Start a conversation in any one of these ways: with a probing question. You learn about these silly terms in tech-land. Open, Closed and Probing questions. I won't talk about them. Ask her this, I mean it, ASK HER THIS, as you have said yourself that you've been busy with work:

Have you had enough free time from school to see any movies recently (or over the holidays)?

This, starts the conversation. You've started a topic and left it open for her to answer you. The chances that she's gone and seen 1 lonely movie, are quite high, so let's pretend she saw one movie with her brother and she didn't like, Spy Games for lack of a better choice. If you've seen it, listen to her answer, do not have one prepared. Don't interrupt her despite the fact that I did that before. Not being interrupted means you are listening to what they have to say. I think I've talked about that briefly in another article. If she liked it, ask her why. If she didn't, same thing. Once you have an answer to that, it's your turn to divulge some info. If you keep on asking questions, it's a one-sided conversation. If you've seen it, be honest on whether or not you liked it. The WORST thing you could POSSIBLY do, in my personal opinion, is pretend to be something you're not for a "good" first impression. It's so totally phony, I want you to burn it out of your head as an option. Same thing with lying, becuase that's phony too, burn those thoughts. See if she asks any questions, but be ready to keep on talking about the movie. She'll jump in if she's going to ask. Copy her type of reply to your questions. If she talked about what was funny, tell her what you thought was funny, sad: sad, stupid: stupid, awesome: duh. Ask her if she's seen, The Lord of the Rings. No soul should be without such an experience. This... this my friend is where you have to hold on to those two "friends" of yours (not too tightly of course), and keep them with you! Now that you've opened the topic of movies, talked about one (or maybe a few if you are able to have a good conversation!), ask her if she would go see it. Like this:

Conor: "I thought it was stupid in Spy Games when blah."
Goddess: "I didn't think it too bad."
Conor: "Have you seen, The Lord of the Rings?"
(reponse1a NO)
Goddess: "No, I haven't."
Conor: "Are you interested in seeing it?"
(MISSION: COMPLETE)

(reponse1b NO)
Goddess: "No, I haven't but I've heard so much about it."
Conor: "You have to see it, it's amazing, it's beautiful, it's a great movie."
Goddess: "Is it?"
Conor: "It is. You've got to see it, I'll take you to see it, because you've got to see it."
(MISSION: COMPLETE)

(response2 YES)
Goddess: "Yes, I want to see it again." (she HAS to have liked it)
Conor: "Are you able to see it Friday night?"
(MISSION: COMPLETE)

You might think those are lame victories, but they are not. You've taken step #1. The ball is in her court.

Don't... give up if this does not work. Be strong. Keep those testicles where you can see them and don't let them budge. Because she might want to know that you really DO like her enough to ask her out to a movie, and that you're not a wuss, because Conor, you ain't. Don't hold back. Keep on trying for something, you've seen how easy it can be. The only thing that might get in your way beside the faint possibility that she doesn't like the way you look (and if you didn't know already, every single last one of my female friends, find you to be a hottie,with a sexy voice!), show her you are interested in her. How'd you like to be pursued? I bet you'd love it. So... follow that Golden Rule, and do unto others as you would have done unto you. Now when age plays a role, like an older, or younger but highly, intelligent woman, figure out where they stand on the age barrier. How many years this way or that way is too many, and whatever you do, don't date them for their body or wicked ways. Date them for who they are, otherwise it won't work because one of you will feel uncertain I bet. But don't let age play that big a role... when you're 20-something... that phrase came into being because you can't tell a 20-year old from a 29-year old, honest.

Peace brother, and best of luck. Post Qs and reply to this too, unless you feel a rant coming on.