Before you read all these unspoken rules, the #1 Rule is Don't Sweat Over the Rules!
The worst dates are when you're so nervous about breaking a "rule" or saying the wrong thing, that the entire date becomes stiff and unnatural. If you say or do the "wrong" thing, you'll be fine. If you're building a real relationship, it should be able to handle some natural missteps.
Super helpful audio for new daters - Driver's Ed by the Nasi Project
The First Date:
The first date is generally 2-3 hours long. The clock starts when you knock on the door. Not when you get to the lounge. Make sure you have a watch so you can keep track of time. Be smooth about it.
Know your own personality. If you’re not the type to do well in a lounge, i.e. your personality doesn't shine when talking to a brand new stranger for two hours while also cheshboning how much lightning chemistry you have, then go somewhere else. You don’t get points for doing “what everyone else does” if it doesn't work for you.
Stock your car with 2 bottles of water, straws, and tissues.
Bring a fully charged phone, multiple credit cards and some cash.
Arriving up to 5-10 minutes late is understandable. If you are running later than that, let the Shadchan know.
When you come into the girl's house, you can expect the father to ask you how the drive was, what you’re learning in yeshiva, etc. You may want to have a little dvar Torah prepared if that’s the kind of circles you’re dating in.
Sometimes the parents will call the girl downstairs when they decide you're ready to leave. Other times, the girl will be sitting with her parents when you come in.
When you leave the house, your first words can be something along the lines of, "Your parents were so nice," or "How are you?", "How was your day?" etc. or something about finding parking right outside.
Open the car door for her.
Once you’re both seated, tell her where you plan on taking her. Ask her if she is okay going there.
At some point on the date, excuse yourself to go to the restroom. This way the girl will feel comfortable taking the opportunity to use the restroom as well.
When you drop her off at her home, wish her a good night and it was nice meeting her. Don’t ask her how the date went. Don’t tell her, looking forward to next time.
You can walk the girl to the door as a kind gesture.
General Advice:
Give your date a heads up if you are going for food so she knows not to eat beforehand
Give your date a heads up if you are NOT going for food so she knows to eat beforehand
Getting a snack and then sitting somewhere is the way to go (Ice Cream, Dessert etc)
Find out if the girl has any allergies prior to going for food.
Take note of her favorite drink or snack and bring it on the next date.
When sitting down to eat, offer to pour her water before pouring for yourself.
When getting food, clarify with the girl if you plan on just getting desserts or a full meal.
It's recommended to let the other party know the nature of the date. (i.e. activity, lobby, dinner etc)
Have an idea of where you are going before picking up the girl - saying, “whatever you want” isn't flexible, it's lazy
If you ask the girl for her preference on something and she doesn't care, you go ahead and make the call. For example, if you ask her what table she wants to sit at, or what side of the table, and she says she doesn't care - just choose. Don't stand there waiting.
Always have a backup plan if the hotel has no place to sit or an activity is not working out.
Dress for success. Regardless of whether you aim for a formal or casual vibe - clean, neat, tucked in and pressed is the ONLY way to go.
When you are picking up and dropping off - please attempt to park in the closest spot to the front door, even if that doesn’t end up being so close. If there’s a spot in front of the house, just K turn.
Try not to drive away before you can confirm she successfully got into her home.
Don't say names of people you previously dated.
Don't bring up engagements, vorts, or proposals as a topic on an early date. The girl may freak out.
If you need to re-tuck yourself in, don’t do it in front of your date
Check if she is wearing heels before you decide to go walking on the boardwalk.
Keep your car clean. Do not to have anything on the front seat or garbage floating around the passenger side.
She is a girl, not your Chavrusa. Please don't date as if you're arguing with a Chavrusa.
Don't comment on her outfit, hair, etc, at least for the beginning dates.
Don't talk negatively about yourself or your family. Present yourself and your family in the best light.
Don't bring up on early dates how hard Shidduchim is for you.
As a reminder when planning, if your date is from the area, it might be distracting to go out locally. This isn't a "rule". It's being considerate.
Face the Waze/Google Maps/GPS in a way that the girl can see it.
Put your phone on Do Not Disturb mode.
Don't check the time more than once or twice. It gives off the impression that you are desperate to get home.
If you're sitting in a popular dating spot, try not to compare your date to other couples that seem to be having more fun. Focus on the person you are with, unless you're both spying together:)
After the Date:
It's expected to give a response to the Shadchan by the next morning. If you need more time to think about it, express that to the Shadchan so they know what's going on.
Even if the shidduch idea doesn't work out, it is appropriate to send a token of appreciation to the Shadchan. That can be a check, gift card, a chocolate platter, etc.
Some ideas include: Yossi's Sweet House (they ship throughout the US), Cookie Corner (Brooklyn and Lakewood).
Dropping the Shadchan:
When dating progresses to the stage where direct and uncomfortable conversation can be communicated directly between the two of you, it's acceptable to "drop the shadchan." That includes planning the dates without a Shadchan, Erev Shabbos phone calls/FaceTimes, etc.
As the guy, it is expected of you to make the first move. Find an agreed upon time for you to call her to plan the next date.
Call her before Shabbos, or at the very least, a Good Shabbos text.
If there's a fast day, wish her an easy fast and ask her how it went after the fast.