Want to make a good impression on the women you’re with? 

Here are some suggestions to help your date realize that you're a genuine mensch:

Let her know the venue for your date 

That way, she can feel that she’s dressed appropriately.  Since men’s wardrobes are often much simpler than women’s, some men may not realize that she won’t enjoy your plan to walk through the Botanical Gardens if she’s not wearing comfortable shoes,  and a date in a hotel lobby requires a different wardrobe than an afternoon at an amusement park.  If your date is too overdressed, underdressed, or inappropriately dressed for what you’ve got planed, her level of discomfort may derail even the most promising shidduch.

Food is important!

Frankly, we’d prefer that couples not go out for a three-course meal on a first date.  Two people who barely know each other are better off concentrating on their conversation rather than figuring out how neatly they can eat without getting sauce on their face or lettuce stuck between their teeth.  However, it’s important to include some kind of refreshment on every date.  Either plan to meet for coffee, dessert, or drinks, or in the middle of your date stop for something.  It’s not enough to casually ask your date if she’s hungry or thirsty, since she may be embarrassed to say yes.  Instead, we suggest saying, “I think it’s a good idea to get something to drink/eat. 

What can I order for you?

If you’re planning to go out to dinner, say so when you arrange the date, so she won’t eat beforehand.  If you’re budget conscious, pick a moderately priced place, rather than telling your date what price category she can choose from (yes, there are men who do this, virtually insuring they won’t ever have a second date).  And what if you’ve arranged to meet for drinks after work, or for coffee, and the conversation is so interesting that your planned 90-minute meeting stretches past the 2 ½  hour mark?  Your date is probably hungry, and if she came straight from her job she’s famished. Be a gentleman and say, “I can’t believe how the time has flown.  It’s a lot of conversation for one drink, and you may be hungry by now. There’s a nice kosher café a few blocks from here – why don’t we get something to eat?”

Not chasing a man doesn’t only mean not expressing, “I really, really like you” before he’s ready to hear it. It also means not telephoning him to see if he wants to go out again, making it clear during a date that you expect him to want to continue to go out, or calling him up if you haven’t heard from him in a few days.

Your grooming’s important, too

After a long day at work or on motzei Shabbos, shower, shave, wear fresh clothes, and use a little cologne.  Your date will notice when you don’t.

Do advance planning

You’ll make a good impression if you appear to have covered all of your bases before your date.  Know where you’re going and how to get there.  Carry enough money and credit cards, so you don’t have to stop at an ATM.  Daven mincha before you meet her, so that she doesn’t have to wait in your car or on the street outside a shul so you can chap a minyan. Have an alternate plan in case the restaurant, museum, or program you’ve selected has an unexpected closure.   And if you’re planning to pick up your date and you don’t have a car, don’t ask her to call you a taxi; have the driver wait at the curb while you go inside to meet her. 

Don’t leave the plans to her

You’re right, she won’t like someone who’s too controlling.  But she’ll also feel uncomfortable if you ask her out and then put her in charge of deciding what to do.  Instead of, “What do you  feel like doing?” consider “I thought we might do X or Y.  Which do you prefer?”  If she can’t make a choice, don’t unfairly conclude that she’s indecisive.  Many women are uncomfortable about making a choice the first few times they’re out with someone.   

Always be a gentleman

Okay, her looks are not what you expected, or whatever you’ve been told about her is totally off.  Neither circumstance is her fault, and it’s not fair for you to take out your disappointment by being mean or rude.  Be courteous and polite, because another human being should always be treated this way.  In addition, your date, or the person who set you up, might decide that even though this idea didn’t work out, you’re a good man who’s perfect for someone else.  They won’t offer to set you up if you’ve made a bad impression.

Make sure she gets home safetly

If you’ve picked her up, you’re responsible to take her home, or at the very least to get her a taxi and pay for the fare.  If you’ve arranged to meet, ask her how she’s getting home; in many circumstances, especially if it is late or public transportation is infrequent or isn’t close by, it’s appropriate for you to drive her home or get her a cab. We suggest that even if she plans on going home on her own, you take her to the bus or train stop and wait with her until it arrives.

Watch what you say if you already know that you’re not going to ask your date out again

Don’t tell her what a wonderful time you had, or how great a person she is.  That sends a mixed message that confuses her and leads her to believe you’re still interested.  Its better to politely end a date with, “Thank you for meeting me tonight.”  

If you want to ask her out again, call within 24 hours

That means either calling her, or if a third party is making the arrangements, calling the third party.  If you have to delay for some reason, don’t wait more than 48 hours.  She’s as anxious about the call as you are, and if you wait longer she’ll begin to think you’re not really interested and will lose interest herself.  Follow this timetable no matter whether you’re enthusiastic about asking her out again, have to be persuaded to ask her out again, want another date but can’t schedule it just yet  because you have a business trip next week, or had second thoughts after you told her you would call. 

If you said you’d call, call within that same 24 hour time-frame

Make the call even if you decide that you don’t want to see her again.  In that case, you can say, “I enjoyed meeting you last night.  I told you I’d call, but since then I’ve done some thinking and I don’t think that we are moving in the same direction. I wanted to let you know this and to wish you the best.”

Consider whether a woman who may not be right for you may be a good match for one of your friends, co-workers, or roommates

You can telephone her a short while after you’ve stopped dating to say, “Even though it didn’t work out for us, I think that you might be a good person for my friend, Yussie, to meet.  I described you to him and he thinks it sounds like a good idea.  I called to see if you’d like to talk about my suggestion.”