Dear Rabbi,

I went on a first date with a successful man. He asked me out by saying, “I have a birthday coupon somebody gave me, and I might as well use it.”

I was particularly taken aback when the man asked the waiter if there were any exclusions to the expiration date. I offered to pay my share, as I always do. He graciously accepted, I then gave him $20 and he said that was fine.

Am I crazy? Is it really acceptable to use a coupon on the first date, and then go on to grill the waitress about its exceptions?!

-Coupon Questioner


Dear Coupon Questioner,

The first thing that struck me in your question was the way this “successful” man asked you out on the date: “I have a birthday coupon somebody gave me, and I might as well use it.” If he was trying to be witty, he picked a poor time to do it.

When a man is genuinely interested in a woman, he doesn’t ask in such a “jerky” manner. He tries to make it sound a bit more sincere, even romantic. So right off the bat I’m wondering just how interested or motivated this man was about taking you out. Or maybe he’s just really socially awkward? Just because he’s financially successful doesn’t mean he knows how to act in social situations.

Interrogating the server about the details of his coupon was definitely what most people would consider to be in bad taste. I’d say it was simply really bad social etiquette. The fact that this “successful” man took your 20 bucks is also a big sign that he’s either socially clueless or, more likely, that he’s not interested. Either way, not someone you want to be dating.

There’s nothing wrong with a man using a coupon on a date, as long as he does it with class. He has graciously offered to treat you to an evening out in exchange for the pleasure of your company. It’s really irrelevant to you how he pays for that honor, whether it’s by cash, credit, coupon, or gift certificate. All you need to be concerned about is how respectfully he treats you, and how interested he is in getting to know you. In your case, it seems like he failed on both accounts.

You aren’t crazy. Now move on and try to find a man who is successful in areas that count: manners, respect, and generosity.

Best of luck!



Rabbi Arnie Singer dated for 15 years before meeting his Beshert. He offers dating and relationship advice on and on
  1. Dear Rabbi Singer.

    With all due respect I disagree with your assessment.

    I don’t see how one can have a clue about the complete picture of this man from the few details that we know about him.

    This man could be all that a woman is looking for, just a bit nervous
    when taking a date out, this happens to everyone. Additionally his actions do not tell us anything about his level of interest and it can even be the reverse of what you thought. His interest in her may be causing him to be nervous because he’s afraid of messing it all up.

    Taking the $20 is indeed a social blunder but we all make different mistakes depending on our upbringing, but whose to say what that means?
    If he is a good person with a giving heart does it really matter if he needs to learn a bit about “social norms”?

    I am aware of many men who adhere to politeness standards etc. outside their office, but will be awefully inconsiderate to their employees behind closed doors and disnonest in their business dealings.

    How much are these exterior behaviors really worth?

    This woman needs to date him some more and find out about his tendencies that matter most for the long term.

    Thank you,

  2. Rabbi Arnie, you’re so right! A man who is successful at manners, respect and generosity is good husband material and this guy definitely is not that, plus, he does not have courting you as a high priority. If he’s like this now, imagine what he’ll be like after you’re married (feh!). He is doing you a favor by telling you exactly who he is on the first date so you don’t have to waste any more of your time on him.

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