• Walk at her pace.
• ​Notice the ground on which you will be walking. Cobblestones, cracks in the sidewalks, pebbles, sand, etc. are difficult to walk on – especially with heels. Avoid those. Similarly, notice sidewalk grates; those are especially difficult to walk on with heels. And sometimes they let up blowing air which can make for uncomfortable situation. As possible, avoid them, or you walk on those and let her walk on solid sidewalk.

• If there is a possibility of rain, bring 2 umbrellas. Sharing an umbrella generally brings two people in ‘too close for Halacha’ proximity.
• The man should be the one walking on the side closer to the street, so that if a car splashes water, it lands on him, not her.
• Plan accordingly to minimize the time outside in the rain. If it is raining, plan to go someplace where the parking lot is very close to the destination. If when you come to the destination, and you realize it is too noisy or not conducive to good conversation, don’t just say “it’s too noisy here, let’s go somewhere else…’. Ask her what she prefers. Many girls really don’t like to walk in the rain..

• You are talking with a lady. Do not use the same casual words you might use amongst your friends.
• Most girls do not know gemara terms. And most don’t appreciate the gemara tune in everyday discussion.
• Do not curse or swear.
• Always be polite to everyone you come in contact with – parking attendant, doormen, wait staff.
• ​Do not try to impress with high vocabulary. Be comfortable with your words.
• Do not talk about sports. She most likely doesn’t care.

• If she is driving, it is still best to walk to the driver’s seat to open the door for her, and then walk around the back to the passenger seat.

•  

  ​​Don’t feel obligated to open the car door for her when exiting the vehicle. Most people get out of a car as soon as it parks. Successfully opening a car door for a woman so she can exit will probably require you to say, “Hey, don’t get out. I want to open the car door for you.” She’ll then have to sit there and wait as you exit the driver’s side door and circle around to the passenger’s side so you can open it. You’ll just create a spectacle and may make your date feel like she’s being chauffeured instead of courted.

• Don’t force the gesture if it’s just not possible to perform.

•  

  If there’s not much room between your car and the car parked next to you, let her open her own door.

•  

  Before shutting a car door, make sure everything is inside the vehicle – skirt bottoms and purse straps, etc. You don’t want to ruin your date by slamming her foot in the door or tearing a dress. Give a quick check to make sure everything is safely inside. You might even ask, “Everything in?” before shutting the door just to make sure. And definitely make sure that she is in the car before driving off.

•  

  If you are already in the car, should you get out and go around the car to open the door? Proper etiquette says yes. Today, most bochurim do not do that, and most girls do not expect that; there are always some girls who do expect it. Some bochurim lean over from the driver’s seat to open the door. At the very least, make sure the door is unlocked so that she can enter the car. (It is generally understood that most bochurim would not jump out of the car to open the door for her in Crown Heights, but outside of Crown Heights, it is more common.) Walk behind the car to the driver’s seat.

•  

  Always try to open the door for a date when she enters the vehicle. If you don’t have anything obstructing you, always open the door for your date when entering the vehicle. You should have cleaned your car before the date, but if you have any crumbs or other gunk in the passenger seat, sweep it off before she sits down.

To note:

• Not all women like having doors opened for them. Some women are more empowered these days so they may take it the wrong way if you try and open up doors for them. If she tells you that she isn’t comfortable with you holding doors open for her, just respect her choice and do not make a big deal out of it.
• Don’t expect consistency. She might open the door herself in an evening, but then the next time she’ll step aside indicating that she wants you to open the door for her. So watch for that and read her body language. And don’t analyze it, it is just the way she is.

• There are so many things you can compliment a woman about besides what she looks like or is wearing. She most likely did put some time into working out what she will wear and how she will make her hair. But most likely, she will not appreciate that all you notice is the way she looks. Even if you think she does look nice, hold back from saying it. Save those compliments for later in your relationship.

•  

  Instead, compliment her on something she does well or that she has an interesting perspective. And use descriptive words to show that you really do appreciate that particular attribute. Don’t only praise the person, praise the action.

• Sometimes the best compliment is actually taking on her perspective, ‘I never thought of it that way. I like that. I will do that from hereon.’ Or during a later date, mention something that you are doing differently because of something she said. It is not so much the words of the compliment as the words reflecting your mode of being authentically complimentary.

•  

  Only once she knows that you appreciate her as a whole person, might you also compliment the ways she looks.

• Opening doors for women requires their cooperation. If you get to the door before a woman, opening the door is simple. Just open the door and hold it for her. Things get awkward when you and she arrive at the door at the same time or she gets there before you. In these types of situations, opening doors becomes much like a dance. Each person has a role they need to fill for the operation to successfully work. If she arrives at the door before you or at the same time as you, she should step slightly to one side so that you can open the door without knocking her. If she opens the door for herself, that’s not a problem. See below.

•  

  Do not be too eager to help her open doors. Do not push her aside just so you can open the door for her. Do not run towards the door just to get there before she does so you can open it for her. You can take longer strides just before the door so you are there a second before her.

•  

  If she has already started opening the door, just assist her. If she already has her hand on the doorknob and has already opened the door, don’t swat her hand away and then say “allow me” or “I insist”, that is just plain insulting. Just put your hand on the edge of the door and help her open it further. Basically, don’t make a big deal about it.

•  

  If the door swings in, go through the door first and hold it for her. Doors that open inwards can prove tricky for any gentleman. The best way to go about them is to go through the door before she does in order to hold the door open for her. If she arrives at the door first and begins pushing the door open, stand on the side where the door hinges are and simply extend your arm over her head to take the door’s weight from her as she passes through.

•  

  Try to avoid the situation where you’re standing in the doorway holding the door open with your back. You don’t want your date tripping over your feet or having to squeeze herself between you and the doorframe. Also avoid the position where you’re standing at the door sill, on the side opposite the door’s hinges, holding the door open with your hand. This will force her to duck under your arm as she goes through the door.

•  

  With double doors, open the first, but not the second. When there is a door, and then an entryway airlock area, and then another door, open the outside door, allow her to step inside the airlock, and then for the second door, do as indicated above and simply help her open the door as she goes through. She may wait inside the airlock for you to open the second door entirely, and that is fine, of course.

•  

  With revolving doors, reach out and slow it down so that she can step in. This rule is especially true for older revolving doors that lack the auto-revolving feature that many modern revolving doors have. Unless the revolving door has large spaces, do not share a cubicle. And never just stop pushing so that she has to push it herself. Many entrances that have revolving doors also have a standard door nearby. If possible, use that one.

• Remember, you should only hold the door open for the woman you are with, and not for everyone else. You should not open the door for your date and then hold it open for many other people to walk through. After your date has walked through the door you should immediately follow her through, but as a sign of courtesy to the people behind you, do not close the door behind you as you go inside. Just let the door swing on its hinges so that the other people can catch it before it completely closes.

To note:  

• Don’t expect consistency. She might open several doors for herself in an evening, but then out of the blue she’ll step aside indicating that she wants you to open the door for her. So watch for that and read her body language. And don’t analyze it, it is just the way she is.
• ​Not all women like having doors opened for them. Some women are more empowered these days so they may take it the wrong way if you try and open up doors for them. If she tells you that she isn’t comfortable with you holding doors open for her, just respect her choice and do not make a big deal out of it.

• If possible, go side by side.

• If that is not possible, there are different opinions. Some say that that proper etiquette dictates that he should always allow her to go first. Others say that he goes down first (using the reasoning that if she falls, she falls on him, rather than down the stairs. And if he falls, he would not fall on her.) For tznius reasons, most girls feel uncomfortable with a man walking behind them looking at her back. In conclusion…

  (But do not say anything about it, like, “Some girls do not like when they walk in front, so I will walk ahead.”)