The Preparation:Usually I start to get ready about an hour before pick-up time. I've probably planned out in my head what I want to wear much earlier in the day, so I take it out of my closet and lay it on my bed. I look at it, consider it, try a few different variations which turn into totally new outfits, and, after much playing around with options, end up putting on the outfit I originally thought of. Then I try to do something with my hair - usually putting it in a half pony or pulling some of it to the side in a clip, and also usually ending up unhappy with my hair in general. I put on a little bit of make up, but not too much because I'm not super comfortable in make up and I don't think it's very pretty when girls look like they're wearing too much of it.
The Wait For Pick-Up:
I'm usually ready a while before I'm supposed to leave (except for one time when the guy came 15 minutes early). Then I just wait around, usually hang out online nervously doing nothing. This is when I start to wish I wasn't going out because I get kind of anxious and would much rather curl up and watch a movie or something instead.
I often do not know what we are doing on the date. This is somewhat of an inconvenience because I don't know A. whether I should stay dairy and B. if I should eat dinner at all. I usually eat a snack in case we are not going out to eat, because I've ended up pretty hungry on dates sometimes.
Except for once, I've never been picked up at home. The guy usually calls either on the dot or about a minute after the allotted time and I go down from my dorm/apartment. If the guy is noticeably late - I don't mind, but I start to worry that maybe he forgot. Most girls probably wouldn't worry - but I tend to worry about these things. :) Especially if we have not spoken in a week.
The one time a guy came to my house, I had no idea what I was supposed to do. Do I invite him in? Do I just leave with him? Do I ask him if he's hungry, or is that weird because he's not coming to hang out? I ended up asking if he wants a drink, he declined because he said we're going out to eat, and we left. (I'm so glad I don't usually go on first dates out of my house.)
One thing I never know how to navigate is the "Are you hungry?" question. If he wasn't planning on going out to eat, and/or if he's not hungry, then he'd have to change his plans on the spot (and become hungry) if I said yes. If I say no and he was planning on going out to eat, he'd have to change plans the other way (and be hungry the whole date. I might also be hungry the whole date, which is just silly). I usually answer something noncommittal, but once I said yes. We ended up going to a bagel store where the guy told me he wasn't hungry but I could get something if I wanted. That was just AWKWARD.
I think date activities really ought to be discussed before actually going on them so you can both be prepared for whatever it is you are doing.
Car: I follow the guy to his car and stand there awkwardly as he opens the door for me. It's not that I'm this super feminist who gets offended if a guy feels he needs to do things for me. It's just that people don't usually open car doors for me, and I feel a little silly when a guy who, in all honesty, is a complete stranger does so for me.
Subway: Walking to the subway is actually not as awkward as getting into a car. For one thing, the guy can't open the subway door for me. It's also a good little walk to start the date on. We can start talking to each other without him also having to deal with driving anywhere. The wait for the subway can sometimes get a little awkward because you're just standing there. When the subway finally comes, you have to decide what you're going to do - stand? Sit next to the guy? Would he feel weird about that? If he offers you the only seat, do you take it? Or do you offer it to him back? Do you just stand with him and neither of you take the seat? What if you don't like sitting in between two strangers on the subway but he offers you the seat?
By car: The problem with me and cars is that I tend to stare out the window and lapse into silence during car rides (ask anyone who's been on a car ride with me). I have to tear myself out of that element on a date and make sure I talk. I don't really mind the car ride, though, as long as the guy's not a crazy driver. I've been in car rides where I was silently praying we would make it to the date and back in one piece. Those kinds of car rides are NOT pleasant.
By subway: I feel very conscious of the fact that there are a lot of people around us. There is usually not too much conversation on the subway, but if too much time goes by without conversation, that can get awkward. Usually we talk a little bit on the subway. If there are other Jews on the subway, I'm also very conscious of how much we look like we're on a first date. I especially hope not to see anyone I know.
The entrance in this case most often refers to entering Starbucks. That is where I have been on probably 75% of my dates. (Bo-ring. But understandable from the guy's perspective.) The guy often asks me where I'd like to sit, or if a particular spot is okay with me. I prefer sitting somewhere away from any window where we won't be super obvious to passer-by. I like to sit somewhere a bit apart from other people, since I find first dates awkward enough without other people being able to see and hear us being awkward.
I find first dates difficult - and this part is the most difficult. In my dating experience, I've never been hooked in a conversation by this point. Usually, I'm floundering around in my head trying to come up with interesting things to talk about, while simultaneously not being super interested in what the guy is saying. I try very hard to be interested, but I often find myself becoming bored, and, unfortunately, my mind starts to wander. I'm not always aware of my mind wandering until I snap back into the conversation and can't remember what the guy was just saying. This is bad. Every time I go out, I work on not doing this. Sometimes I feel like this is why first dates at Starbucks are a bad idea. When I become friends with someone, it's usually because I first met that person while doing something fun and we both had a good time together. I know people who feel differently, but in my opinion, first dates should probably be more activity oriented instead of putting yourselves in a position where all there is to do is talk. If you both have fun doing whatever activity, then you'll be more interested in finding out more about the person. Or I will, anyway. Of course, there should be some talking on a first date. But there should also be something fun to do. Some experience to share. Something that engages both parties in the date itself so that there isn't such heavy focus (and pressure) on pure conversation. An activity also gives daters something shared to talk about. Then they are not two random, separate people trying to be interested in each other but they are two people participating in the same activity and sharing an experience. Shared experience is usually what brings people together more than forced conversation. And it leads to more natural conversation.
I'm usually ready to go home waaaaay too early. That makes this part of the date even harder. I tend to become a bit more withdrawn and reserved when I've really had enough, hoping that will kill the conversation sooner. I also have no desire to share more of anything personal (or as personal as you get on a first date) with the guy if I'm really finished dating him. I do make an effort to keep the conversation going if I feel a pathetic amount of time has passed, though. I definitely try to give us a chance to interest each other in conversation in various ways, but at a certain point, I just feel bored-out. Once a nice amount of time has passed, I kind of try to steer the date toward its end without being too obvious about it. I always let the guy decide when he wants to end the date.
The end of the date is slightly awkward because eventually, when conversation really sort of dies, the guy says, "So...should we go?" I have to make sure not to sound too eager when I say, "Sure."
The Drop Off:
In my experience, I've never really felt like I wanted to go out again with the guys I've dated. Still, even though I have to make new forced conversation on the way back, I'm happy and usually much less tense because we're going back. I find awkward date conversations tiring though, and I don't usually want to talk anymore, but I do anyway. The one time I really felt annoyed at a guy at this part of the date was when he made me come meet him near his work, and then just dropped me off at the subway instead of taking me back. As much as I wanted the date to be over, I thought that was very rude of him.
I never know what to say once we get to the front of my building. I always thank the guy and say I had a nice time. The guy also usually doesn't really know what to say here and we both fumble around for some acceptable way to leave each other that isn't too awkward or abrupt or dragged out. Only once did a guy tell me right there that he wanted to go out again. I felt very put on the spot because I was pretty sure I did not want to go out again, but I didn't feel ready to say so just yet. I said, as noncommittally as possible, "We'll talk." But I really did not know how to respond. I needed time to decompress from the date before really deciding.
I usually agonize over my decision to go out again or not. I never feel like I had a good time on a first date (seeing as I don't find sitting in Starbucks having forced conversation particularly fun) so I'm not too keen on repeating it (hence the suggestion of actually doing something on a first date, so that even if you're not crazy about the guy or don't feel like it will really go anywhere, you still feel like you did something fun with him and are more willing to repeat that fun experience and give him (and yourself) another chance). Unless I feel very strongly like the guy I went out with is weird or a creep or completely not for me (has happened a few times), my policy is usually - I'll go out again if he wants to, and if he doesn't, that's fine, too. Usually we mutually do not want to go out again and that's that.
Other thing I recommend: don't stalk the girl to set you up with her friends after you both decide not to go out again. It'll probably ruin any chances of her doing so.
This is shallow (and everyone is more shallow than they admit to being. I don't believe you if you say otherwise), but if I found the guy really attractive, I'll probably actually want to go out again, even if our conversation was forced that first date. Unfortunately, this has not yet happened. :-/ If I find the guy extremely unattractive, it'll actually feel a little icky to sense him looking at me in certain ways. This has happened. :-/
I always have this desire to say to a guy, "I hate how awkward shidduch dating gets. Let's pretend we're not on a shidduch date and just do something fun." I never have the nerve, though.
I think guys should refrain from talking about wanting to find a girl to fall in love with until a bit later in the dating experience (as in, not on the first date).
Guys on a first date should also refrain from talking about times they got drunk and ended up in the hospital.
Guys should also not completely abandon a girl after a first date.
Don't express wonder at people actually stopping at Stop Signs.
I wonder where all the really quality guys are and why I never go out with them. :-/