The Jewish world is no stranger to the drama of dating. When singles mingle, it can cause a tingle but when they clash, the bash will crash.

As they say, it “takes two to tango” so, without a willing and capable partner, dating can be extremely awkward and unpleasant. The best antidote for saving a dying date is a healthy dose of scintillating conversation, the kind that gently touches nerves without pressing buttons. On a successful first date, the banter should leave you feeling stimulated and entertained as well as challenged and perplexed. Ideally, the date should leave you with more questions than answers. That said, the date likely has gone south if the only burning question you have is directed to the waiter: “May we have the check please?”

Of course, sometimes the conversation on a first date can get a little too interesting. The more people talk, the more they reveal and, sometimes, the revelations can be counterproductive to connectivity. It is a fine line to walk (and talk) because some interaction is required on a first date. Otherwise, it would just be a highly uncomfortable staring contest.

For purposes of illustration, below are fictional examples of first dates gone awry based solely on how the conversation unfortunately unfolded:

Example #1—Common Ground

Gal: “So, tell me something about yourself. Let’s see if we have anything in common.”

Guy: “Sure thing. I grew up in New Jersey but I don’t like to admit it.”

Gal: “Me too. Go on.”

Guy: “I don’t like strawberries but I enjoy strawberry ice cream.”

Gal: “Same here. So far, you’re two for two. Continue.”

Guy: “Let’s see… Oh yeah… I did time.”

Gal: “Excuse me! You were in prison? You’re a criminal? Sorry, but that is an absolute deal-breaker.”

Guy: “No, no, no. You misunderstand. I did ‘Time,’ as in, I did the cover of Time Magazine.”

Gal: “Are you saying that you were actually on the cover of Time Magazine?”

Guy: “Yes, that’s exactly what I’m saying.”

Gal: “Well, that is impressive. “Why, pray tell, were you on the cover of Time Magazine?”

Guy: “They were doing a story on antisemitism.”

Gal: “But why were YOU on the cover?”

Guy: “Because I’m a self-hating Jew.”

Gal: “Well then, hating you is now another thing that we have in common.”

Example #2—Shayna “Pun”im

Gal: “So, what do you do for a living?”

Guy: “I own a barbershop in Brooklyn called ‘Ha-MaCOMB.’ It’s a play on words. Get it?

Gal: “So, before the High Holidays, do you offer a special BRUSH-Hashanah deal?”

Guy: “That is very good! That would fit with our special SHAMPOO-rim deal on the 14th of Adar.”

Gal: “Since you specialize in men’s hair, perhaps you could host newlyweds for their SHAVE-a Brachot.”

Guy: “I’ve been on a lot of dates but, I must say, you are definitely a CUT above the rest.”

Gal: “And I appreciate your RAZOR-sharp wit.”

Guy: “Alright, I’ve heard enough. Will you marry me? I’ll book a venue in Crown Heights.”

Gal: “Yes, I will marry you. I was thinking of a wedding in Borough Park rather than Crown Heights but… let’s not split HAIRS.”

Guy: “Ok, you can stop with the puns now. You’ve already won me over.”

Gal: “But I POMP-adore you.”

Guy: “I said you can stop.”

Gal: “But I have a SIDE-burning love for you.”

Guy: “Okay, now it’s just getting weird.”

Example #3—A Promissory Note

Guy: “Did you make any New Year’s resolutions?”

Gal: “Yes, I promised myself, blee neder, that I would not make any resolutions, blee neder.”

Guy: “But if you ‘blee neder’ your own promise to not make any resolutions, then you technically have not really made a vow to abstain from making a non-blee neder resolution and thus you might wind up actually making such a resolution.”

Gal: “That’s true. It’s quite a conundrum.”

Guy: “You might be better off not making any promises or resolutions.”

Gal: “You are so right. I will not make any promises or resolutions.”

Guy: “Good.”

Gal: “You have my word…”

Guy: “Don’t say it!”

Gal: “Blee neder.”

Guy: “Oy vey.”

Final thought: It is wonderful when you meet someone special and they take your breath away, but not when you are deep sea free-diving. It is splendid when you meet someone and you fall head over heels, but not when you are working a high-wire without a net. Finally, it is fabulous to fall in love at first sight, but not when you’ve been declared legally blind.

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By Jon Kranz