I don't really have a set way of getting ready for a first date, especially since as time goes on I get more and more lax about trying to look amazing (for better or worse, I guess).
Anyway, here's how I do it:
The dates that I've been on have ranged from pretty casual to yeshivish lounge dates (ugh hated those), but no matter what the venue, I wear work clothes - nice skirt, sweater, definitely no Shabbos clothes or dresses. I haven't worn denim to a first date (except once, which is a different story because we went somewhere after he and I met in a casual setting). I iron my hair to make it less frizzy and always hope that it will magically become shiny and bouncy so I can wear it down, but 99% of the time I end up just putting it back in a ponytail. Then comes the contacts vs. glasses debate - I don't find contacts very comfortable, but I look better in them, so I will opt for contacts unless I'm feeling particularly lazy or tired. If I put on makeup without remembering to put in contacts first I'll usually just leave my glasses on. Makeup-wise, I try not to wear too much (also, I've been told that guys don't like it when girls wear too much makeup. But I find that hard to believe. Or, maybe we just don't have a mutual idea of what "too much makeup" actually means). The whole process can take about an hour and a half or so because it takes me a while to choose what to wear.
Getting picked up:
This is always awkward. I like for the guy to call and tell me when he's downstairs (I do not date from home). When I was living in a dorm I sometimes liked to have a friend come down with me for moral support on her way to the library or something; when I lived in an apartment building the doorman would pretend not to look. As I head downstairs, I hope hope hope that the guy is relatively cute and nice to look at. Haven't had too much luck in that department unfortunately. At the very least, I hope the guy is at least five or six inches taller than me. It's been like 50-50 with that.
When I do see him, I say his name just to make sure it's the right date and I identify myself. I try to smile, and hope he does as well, because otherwise he comes across as bored and cold. The first few minutes are super awkward -- do you a) ask what he has planned, b) ask how his day went (quite frankly at that point I could give a rat's butt about how his day went), or c) yammer about nothing? I pick a) and c) usually, not necessarily in that order. I like to ask what we're doing because it segues into the next question, which is transportation.
The car (or the cab) (or the subway):
If a guy is driving his own car, I always get very nervous because I'm an anxious backseat driver and guys tend to drive too fast and tailgate. I don't really care what kind of car he has or even if it's all that clean, as long as I'm not sitting in crumbs. Points if the car is cute. I don't like to have the door opened and closed for me. It's just silly, in my opinion. That's a matter of personal preference and I'll usually say so before we get to the car. If he opens the door before I have a chance to say anything, I'll try to gently say so the next time we get in/out of the car. Also, the bad thing about driving on a date is finding a parking space. Annoying as hell in the city. If it's cold out, don't park too far from where you're taking me just because it's cheaper. If I'm cold I'm gonna be pissed and you don't want that.
If we take a cab, it's a HUGE turnoff if the guy doesn't know how to hail one. When we do take a cab, PLEASE DEAR G-D LET ME GET IN AFTER THE GUY. It's really awkward to get in a cab first, because all I think about how the guy is probably staring at my butt. If it's a cute guy, I don't mind as much (yes, I'm shallow). If I am turned off by his looks, thinking about how he's looking at me makes me jittery.
If we take the subway, I prefer for the guy to let me swipe his Metrocard instead of my own. It's not that much; don't be cheap about it, unless I have a monthly pass and it won't cost me extra. I don't particularly like waiting for the subway, because the lighting in subway stations is really unflattering and it's hard to have a conversation with trains roaring past. Also, when we get on the subway, if there are empty seats, I like to sit. For some reason, guys always stand. I understand that he might not want to sit next to me, but particularly if there is an empty bench, just SIT DOWN! Do you think it looks more manly to lean against a germy pole?
I'm not a fan of Starbucks as a first date place: the chairs aren't that comfortable, you don't really have any privacy and I don't like coffee or tea all that much. Past that I'm really okay with anything as long as I don't have to walk too long in the cold. I have been to some lounge dates and they aren't that bad -- provided that the company is good. Honestly, going to a lounge isn't that different from going to Starbucks except that the lounge tends to be more pricey. Don't go somewhere where you can't talk, i.e. to a concert or lecture. And when I order water, it's because I honestly hate soda. Not because I'm on a diet.
In terms of the guy getting an alcoholic drink: if you're driving, DON'T! It looks really irresponsible (even if you can supposedly hold your liquor). If you aren't driving, go ahead, but one is enough. Don't get more than one, even if it's just lite beer.
UGHHHHHH. When I get nervous I talk a lot. This means that I usually spend the first five minutes of the date rambling. Or, you know, the entire date. It's really embarrassing and I WISH I could turn it off. Alas. I also tend to talk about me, which isn't so attractive. Whatever. I'm working on it.
Needing to go to the bathroom:
This gets its own entry because it's an issue I have. I really really try not to have to use the bathroom more than once on a date (especially if it's under three hours) but sometimes it's just not in your control. I don't think about it if the other person needs to use the bathroom frequently so I would hope my date would reciprocate. Also, like Bored Jewish Guy, I always work up the nerve to say I have to use the bathroom just as the other person excuses themselves.
Always the awkward part. I've had first dates that were two hours and first dates that were six hours. It's hard for me to remember who indicates that the date should wind down. Probably 50-50. If I have to be at work the next day, I'll ask to go back before midnight because I do need to get sleep. If not, if the date is going well, I'll let the guy make the first move. I do like for the guy to walk me to the door of my building (not to my apartment), unless he can't find a parking space nearby.
Usually a guy will indicate to me if he wants to go out again, mostly by asking, "Do you want to go out again?" If he doesn't, I generally assume that that means he doesn't want to, but I have been wrong about that. If I feel attracted to the guy I mourn the lack of first-date kiss; if I don't feel attracted I am very happy to be shomer. I go inside, he leaves, joy to the world.