I preach "go with the flow," "color outside the lines," "break the 'rules'," "loosen up," yada yada yada. And, I wholeheartedly believe it; there is no set way to do this, and none of this will be true across the board. I realize everyone probably likes to do things a little differently, so this is just based on my own observations and experiences. Only if you're looking for ideas of how to do this, this post is for you.
(As a side note, all this comes after a number of years of dating. I probably would have told you that a lot of this is crazy, had you told me this, in my own words, when I first started this parsha.)
Date One:
This is all about first impressions. Generally you're going out with someone that you haven't met before. You may have heard a lot of good things about him/her, and you're hoping that the date will confirm all of it.
If you're the guy, you may get to meet her parents, and this gives you insight into her family life. If you're picking her up from her house, you get to see where she lives, and this may or may not be information you'll tuck away for later should things progress. Perhaps you'll talk with her parents before meeting the girl herself, and how you greet her when she makes an appearance surely makes a difference.
I remember the first time a fellow who came to take me out on a date looked up from his conversation with my parents and gave me a warm smile as I came into the room. It was early on in my dating career, sure, but it's still sort of troubling that I remember this as a thing, because shouldn't everyone acknowledge the girl they've come to date? I remember, too, the guy who winked at me as I entered; that was a bit off putting. (I'd never met the guy in my life, he's sitting there talking to my parents, and we hadn't yet exchanged any conversation. Not the appropriate time for a wink.) Or, the guy who didn't look at me until we walked out the front door, and then he turned to me and said, "So, what's up," as if the whole scene inside with my parents was incredibly boring and a farce. ...Happy medium! Say hello and be respectful.
Generally, the guy runs the date and picks the location. (A setting in which they can have conversation and begin to get to know basics about each other is ideal.) Sometimes he'll choose to share where they are going and even ask her if it's a good place, and sometimes he'll just start driving. I've been on the receiving end of, "I was thinking about going --here--, how does that sound?" many a times. On the one occasion in which I told him I'd prefer to go somewhere else, he got upset, because apparently I was taking over and trying to run the show. I was confused, because I thought he was asking me where I wanted to go. Turns out it was a formality. Who knew?
I've been asked to help navigate on dates, and that's totally fair. If I had to drive, make small talk with a new person, and follow a GPS at the same, I might also get discombobulated. It can make getting to a location a joint effort as well, and one person doesn't have to feel like s/he takes the blame if they end up driving hakafos around a location because they can't find the right turn off. Collaborative navigating can also help a date in terms of conversation for the car ride.
Speaking of which, this date usually is fueled by small talk. It's about getting a general sense of the person, how you feel in their presence, if you are on the same wavelength (at least peripherally).
Regarding the date's length, that's covered in this post.
Walking the girl to her door at the end of the date is a nice practice even if you think it's all show. A simple "Good night/day," "It was nice to meet you," and "Thank you," is quite enough to leave your date with.
If you're using a go-between, getting back to the shadchan right away is the mentchlach thing to do. After a first date there is little agonizing about whether you want to go out again. Either it's a hard no, or it's a yes...it's only a first/second date after all. The other person is likely waiting to hear back regarding whether you want to see her/him again, and they may be nervous about it. Allay their fears by relaying your decision in a timely manner.
Date Two:
This date is still early, and doesn't hold that much significance. Often people will give someone another date even if they're not really feeling it, because they're giving the shidduch another shot in the hopes something new might blossom. (Oftentimes this does happen, but sometimes the second date just confirms what you may have already known to be true.) Of course, seconds dates can be a lot more than just second chances.
In my opinion, this is a date where the couple needs to do something. Not necessarily "do something" do something, but it should be more than just a repeat of date one. You already hit all the small talk, and you still don't really know this person, so you aren't yet having a deep connecting personal conversation. Therefore, having a fun part of the date (like doing something active, see this post for ideas) could work, or really just changing up the scenery, like going somewhere where there are external distractions so you don't have to come up with all the material yourself. Playing a low-key game could be an idea. Sometimes working questions into the conversation from Loaded Questions, The Ungame, or other like games works too. I've done Myers-Briggs type questions/quizzes too on dates. It's an easy way to get to know someone, by trading Myers-Briggs quiz questions and learning about the person's personality preferences. In the age of the smartphone, it's pretty easy to come up with something.
On a date, once upon a time, a guy introduced me to "Shidduch Bingo." It's low prep, because all you need for the game is two pieces of paper, two pens, and a scissors. The way the game goes is you cut your paper in half, and make one half your bingo board. Draw five rows by five columns, marking your middle space as free and numbering the rest of the open spaces randomly with the numbers one through twenty four. On the second half of your paper, you and your date each write twelve questions. Don't forget to number them! Examples might be: What's your favorite food? What was the last book you read? Or, you could throw in some more intense questions like, What's something you're working on right now? Since it's a second date, you get to decide how in depth you want your answers to be. You can answer that one about what you're working on with a "I'm working on finishing this paper for school," or you could say "I'm working on being more patient with people when they make me upset." The questions get cut up and folded up into the middle. You and your date take turns picking questions at random (and you both answer every question no matter who picked it). After you answer, you cross off that number from your bingo board. First person to get bingo wins! (You can of course keep playing until you've answered all the questions.)
A second date can be longer than a first date, because you have some feedback that the person isn't completely dying of boredom or that they're feeling like it's completely off base. (S/he agreed to another date with you.)
Again, getting back to the shadchan in a timely manner is the nice thing to do. If you need some time to think about things, at least let the shadchan know that, and the shadchan can decide whether this is important information to convey to the other party. Feedback is so important in a shidduch situation. I know I stress this a lot, but it's wrong to go out with someone and give the impression that it's all good and then discontinue the shidduch through the shadchan.
Date Three:
Third dates don't have to mean anything at all, but when you agree to a third date it normally means that there's something there for you. Perhaps it's all on paper, and you're trying to reconcile the intellectual with the emotional, or it's the opposite, and it's all emotional and not rational at all. There is the option, too, that things are progressing nicely, and you "say yes" to a third date, because you genuinely think the shidduch has potential.
Third dates can be longer and a little less formal. It's a good date to begin to get to know what makes the other person tick. If you didn't do something on the second date, definitely do something on the third date. It can be a date that has multiple parts, starting at one location and continuing somewhere else. For example, you can go somewhere and then go for a walk, share a meal, whatever. Having an active part of the date followed with a more serious one is good dating strategy (for this date, or later, depending on what you're up to).
Also depending on what you're up to, the end of this date may be a good time to have a conversation about where you're holding. (Many people will wait until date four or five, but if you're feeling like it has potential and you're getting the vibe that the other person thinks so too, go for it.) Asking a girl out at the end of this date may be appropriate, but obviously don't put her on the spot if she hems and haws. It probably means she's not that into and she was going to "say no," or she really needs to think things over. The proper response to the "I'm not sure," when you tell/ask her, "I had a nice time, and I would like to see you again. Can I call you to set up another date," or some permutation of that, is "Okay, we'll be in touch through the shadchan." Everyone dates differently, and for some the comfort or ease doesn't kick in until much later, and they will keep the shadchan until a much later time.
Same rules apply about calling the shadchan after this date.
I always find that even if a couple is still using a shadchan after date three (to communicate whether or not they'd like to continue seeing the person), there's at least a certain familiarity there, and it's helpful for them to set up date arrangements themselves. I was once on the phone with a shadchan and things started to get complicated, so she called the boy and had each of us on separate lines conveying what the other was saying to each. It would have been easier to just have conferenced the calls, so we could talk directly.
Relatedly, even if a couple has dropped the shadchan altogether, it can be helpful to check in with the shadchan periodically for feedback purposes. This has helped me get through a handful of shidduchim. Because you're still trying to get to know each other and you may not be comfortable to tell everything to the person himself/herself, talking it over with the shadchan who can then relay the important parts to the other person, or the shadchan can give you some perspective on your doubts, can be helpful.
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