Firstly, prepare a דבר תורה in case you would like to tell it to the girl’s father. Also, make sure you have the girl’s address, a place to go (and a backup), a car, and a GPS. Prepare a list of conversation starters. The best idea is to memorize it. As a backup, keep it in your pocket. Some people go to the restroom to check it, but the girl may know this trick and feel deceived. If you take it out in front of her, she may feel awkward, or that the שידוך is not for her, since conversation is not flowing naturally. If you get stuck, use your judgment since every person is different. Make sure you have enough money for parking (which can be in the range of twenty dollars), drinks (sometimes five dollars a bottle), and spare cash. The girl wants to see that you are happy spending money on her, not that she’s not worth the money. In Manhattan, be especially careful when parking on the street. The police there don’t just give tickets to illegally parked cars; they tow them away.
Leave early enough to make sure that you get to her house on time. It’s not right to the girl to keep her waiting in anxious anticipation. When you come in, sit down at the table and let the father lead the conversation. Some say that it’s okay not to eat, while others say not to disappoint the girl’s mother who prepared especially for you.
When you leave, make sure you are not walking too fast for the girl, as wearing high heels may make her clumsy and slow her down. Open the car door for her and excuse yourself for that, if you’d like. Also, excuse yourself for not talking while concentrating on driving. Soft background music is unnecessary but fine as long as it doesn’t disturb the conversation. Try avoiding heavy conversation in the car; it’s sometimes hard to fully concentrate on the conversation while driving. When you get there, ask for her feelings on using the elevator/escalator/stairs. Ask her if she recognizes anyone. She will usually wait for you to start the conversations. When you drop her off, wait until she is safely inside before driving away.
The most important things are תפילה and בטחון.
הצלחה! May Hashem help you find the right one speedily!
