The Dating Playbook

Why activity, dinner, dessert

The plan is set up this way for a reason. An activity gives you natural pauses in the conversation. When you are both focused on something, it breaks up long silences without either of you feeling awkward. Dinner and the activity are interchangeable. If you are taking her out at 6 PM, dinner will usually come first. If you are planning a later date, say 9 PM, the activity will most likely come first.

You do not need all three stops

This is a plan and a guideline, not a rule. If you are going out late, you can tell her on the first date that you are going to a shuffleboard club, that she should eat at home but save room for dessert, and that the dessert place is dairy so she knows what to eat beforehand. That is a great date with only two of the three stops. Sometimes the activity and dinner already ran two or three hours and you need to skip dessert. Never force the full schedule. Every plan comes with a nearby backup for each stop in case a place is closed for an event or the reservation falls through.

Keep some things for later

Do not reveal everything about yourself on the first date. Keep some things to yourself and let them come out over time. Say you are talking about your brother. You can conveniently leave out that he is famous, because it is not relevant on date one. When it comes up on the fourth date, she sees there are more interesting things beneath the surface that have not come out yet.

What she will ask you

In the Jewish world there is a standard set of first date questions, and they come in three parts. These questions are her building a profile of you, so be ready for them.

• Who you know. It starts with the basics: your family. Your parents, brothers and sisters, and what they do for work. Then your friends and their circles. If she is inquisitive she may ask about cousins and extended family, especially if she knows the people you are talking about.
• About you. She wants to know about you, but as the man, ask the questions and listen more than you talk. When she answers, tie your answer into hers. If she says she loves to travel, share the places you have traveled. If she loves sushi, go deeper: what kinds, which places, what was her favorite spot. She learns about you through her own interests, which makes her feel more comfortable and more connected to you.
• What you do. Your work matters. So do your connections to community organizations, the things you are working on and who you are working with.

Questions you can ask her

Keep it light. Ask questions you can also answer yourself once she is done, so the conversation goes both ways.

• What is something most people do not know about you?
• Tell me about your family. Who are you closest with?
• Who are your closest friends, and how did you meet them?
• What do you do, and who do you work with?
• What do you love doing when you have a free night?
• Where is the best place you have ever traveled?

Where this playbook comes from

Before I met my wife I went on around 250 first dates, and more if you count second and third dates with the same person. One month I went on 34 dates, sometimes two in one night. By the end I had seen just about everything. This playbook is what I learned along the way. It is written mostly from the Syrian and Sephardic dating scene, for people roughly 18 to 30, and it fits a lot of the Modern Orthodox world too. If your community moves faster, like the yeshivish world where families handle most of the details and many couples are engaged within about ten dates, take what fits.

The three mistakes I see most

• Taking out your phone. This is by far the most important. Pulling out your phone on a date is a no go. If you really need it, excuse yourself to the bathroom.
• Not giving a second chance. People are nervous meeting someone for the first time. I once went out with a girl where I carried the entire conversation, so for fun I tested how long we could go in silence. It was five minutes before I cracked. We were at an activity, so it just looked like I was focused on it. My friend went out with her after me and married her. She is extremely talkative. She was just nervous. Twenty seconds of silence feels long. Five minutes is torture. That is one reason every plan has an activity.
• Manners. Feet up on the table while you eat, spaghetti with your hands, dropping her off four blocks from her house, rolling your eyes when she walks out of her house smiling. Depending on the person, any one of these can end it, even when you are a great fit, because nobody ever told you what is right and what is wrong.

Always check with your rav

A rabbi is reviewing this playbook, and on anything halachic (Jewish law), from negiah (physical contact before marriage) to taharas hamishpacha (the laws of family purity), you should always ask your own rav or teacher. I give my two cents anyway because most rabbis and teachers never dated the way people date today. Here is one example. A couple was dating but not official yet, so she kept going to summer parties without him. Then he went to a party on his own. Everyone at both parties assumed they were each single. Girls at his party thought he was available, and one of them was her friend. He had no idea any of it was happening. That mess was avoidable, but it is the kind of thing a teacher cannot warn you about, because they never lived it.

The small details she will notice

• Clean the car inside and out. Empty the cup holders and the back seat.
• Set the heat or air before she gets in, and keep the music low.
• Have water, tissues and a phone charger in the car. You may never need them, but if she does, you look prepared.
• Know the parking at every stop so you are not circling the block while she waits.
• If the plan has a walk between stops, check the weather and have an umbrella.

Reading the night

Pay attention to her energy more than to the plan. If she is laughing and asking questions, you are in good shape. If her answers get shorter, she checks the time, or she mentions an early morning, wrap up gracefully. Ending on a high note is always better than stretching a good night into a tired one.