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
Generally, in the Yeshiva circles, wear Shabbos outfits and heels for first and second dates.
Wear something you feel confident in. If you're not comfortable in heels, and will feel they'll be a hindrance to you, don't drive yourself crazy.
The first date is generally 3 hours. If you feel that a lounge will not bring out your personality, you can relate that to the shadchan and maybe get light dessert/coffee with the guy instead.
Let him open the door for you.
Have an opinion, try not to say "I don't care, it doesn't matter" every time he offers two options. Even if you don't have a preference, just choose something.
If he offers something, accept it graciously.
When a boy asks you what you'd like to drink the acceptable answer is to get something. He's asking because he'd like a drink himself and will not get one if you won't.
Make an effort to smile and look happy. It puts him at ease and makes the date flow.
Ask follow-up questions. Don't let the conversation be one-sided.
If you feel unsafe about his driving, speak up!
If you want something specific, ask. The guy cannot read your mind, and more often than not, would love to be of service.
Communication!! Don't expect the guy to be able to read your body language the same way your friends can. You're putting unfair expectations on the guys. They're guys, not mind readers.
Not every guy knows how to talk to a girl. Cut them some slack.
Don't get hung up on the details. Try not to zero in on the "flaws."
Be present on the date. Don't think, "Does he like me?" Think, "Do I like him?"
Don't discuss names of other guys you dated.
Don't talk negatively about yourself or your family. Present yourself and your family in the best light.
Put your phone on Do Not Disturb mode.
Bring a fully charged phone, credit card and some cash, in case of emergencies.
At the end of the date, always say "thank you", "nice to meet you", "I had a great time tonight", "have a safe drive back" etc.
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).
Use the Post Date Eight to tune into if you like how you feel around them:
What side of me did they bring out?
How did my body feel during the date? Stiff, relaxed, or somewhere in between?
Do I feel more energized or de-energized than I did before the date?
Is there something about them that I’m curious about?
Did they make me laugh?
Did I feel heard?
Did I feel attractive in their presence?
Did I feel captivated, bored, or something in between?