The Other Side

In my estimitation, there are over eleventy million blogs out there written by single girls about dating. In fact, studies show that blogging about dates (or lack thereof) has overtaken tzedaka-based square dancing to become the number one pre-marriage activity for frum single girls. But while they’re writing (complaining) about how hard it is to know how to act around boys, people don’t get to see a date from a boys perspective.

Where does she want to go?

You can’t just ask her. The onus is on you to make sure it’s interesting, not too showy, not too boring and leads to a good first impression of the type of person you are. And this is when you know very little about her. You can end up trying too hard. If she’s described as “outdoorsy” that doesn’t mean a five mile nature hike was a good idea. She might be described as “quirky” but taking her for a walk through the markolet just makes her think you have an unusual attachment to the smell of fish, rather than the intended impression that you want to look at interesting things while talking. She might be a reader, but used bookstores don’t smell very nice, not to mention they don’t facilitate much conversation when other people are trying to read their vintage copies of ‘Simple Truths’. You could take her to a hotel lobby, but then you’re just boring and conventional. I know someone who tried a boat ride for a first date. The lesson he learned was, boats can capsize and so can relationships. Can you take her bowling, or will she think you just want to see her from behind? If you offer to go for a walk around a mall does that mean she thinks you’ll spend money on her, or will she appreciate having an air-conditioned place to walk through with a food court?

What should you wear?

This is an easy one if you’re yeshivish or chareidi. Black, white, black, black. (Yarmulka, shirt, pants, shoes). But what if you’re frum yet not yeshivish? What if you want her to understand that you don’t dress a certain way, yet are a certain type? Wearing a white shirt on the first date might lead to a surprise if you wear a colored shirt on the second. Do you wear a bright shirt on the first date to make it clear you like having choice in your wardrobe or will that scare her off by making her think you’re a loud hippy type? Is a suit too formal? Is just a shirt and pants too casual? Will a polo make you look underdressed or will it make you look neat, confident and relaxed? Tzitzis out or in? What if you planned on taking her on a picnic? Do you wear older pants that can get dirty, or will you shock her by looking sloppy? What if it’s the summer? Black wool in the Israeli sun in July? White pants after labor day?

How much can you spend?

Do you spend a lot to show you’re a good provider or will she take that as you being a show-off? Do you spend a little to show you’re thoughtful with money or does that make you look cheap? Do you take out cash to show you can spend money on her, or do you use a card to show you’re careful and possibly have a good line of credit? Do you take her to a nice restaurant or are you trying too hard? Do you take her out to pizza because it’s just a first date or does that make you seem like an inconsiderate schmuck? Can you offer to split the bill so that she doesn’t feel she owes you anything or is that ungentlemanly of you? If it is a nice place do you surprise her and run the risk she already ate, or do you spoil the surprise by telling her what’s happening? What if you do tell her and you get the impression you made the wrong choice? Is it then alright to switch on her to something you think she’d like better, or does that make you appear indecisive? What if you don’t tell her and she feels bad that she either overdressed for pizza or underdressed for steak? Should you ask about food allergies on the first phone call just in case? What if she’s vegan? (Happened to me once at a shabbos table when the brisket was served. Awk-ward.)

Where to look?

You know what I mean. Can you let her know you find her attractive? Will she be flattered and more likely to warm to you, or will she take you as a creep because it’s too early for you to be looking at her like that? (Pro-tip for girls: we’re looking at you like that from the first second. We’re visual creatures and attractiveness is important. We just have to pretend like it isn’t.) When can you compliment her on her appearance? End of the first date? Beginning of the third? (Tip: Compliment the shoes. She’ll think you’re gay and let down her guard.) Is it a faux-pas to have your silk heart boxers peeking out? What if they’re cotton? (Polyester is a no-no. Poly-blend is only okay if the ratio is 30-70 or less.)

Music in the car?

This obviously only applies if you’re driving. Will playing Jewish music while you drive give her the impression that you only listen to that or are a certain “type”? Will she be turned off if you play secular music, thereby not even giving you a chance on the rest of the date? Is speed metal a bad idea in any circumstance (Answer: yes). Will talk radio bring out her strange political views or reveal her as a simpleton who has no idea what’s going on in the world? Which is better? Will no radio create an awkward silence? Should you play Weird Al on the chance that she likes him and therefore solidifies her in your mind as the woman you better marry, pronto?

What do you talk about?

If you give a devar torah are you being preachy? If you talk about college are you being a show-off? (If you attend anything at Landers or any other Touro affiliate, don’t worry about the last one. Knock yourselves out.) What if you get so nervous you forget the ending to the devar torah? Do you flub it and hope she doesn’t notice? (Really? That pasuk is referring to how we should try to be like the chocolate chip and not like the cookie?) Do you try to have topics written beforehand or is that trying too hard? I know someone who went with a whole list in his pocket of conversational topics that people had recommended. Do you want to be the guy who during a moment of silence fishes a crumpled up piece of paper from his pocket and asks “so tell me about your fascism. I mean, famine? Sorry, family!”

This was a long post, wasn’t it? And you know what? We’ve barely covered half the things to think about when planning a date. So next time you’re fussing about what shoes to wear based on how tall he’s expected to be, please, spare a thought for the boys. It’s no picnic either. Do you want to go on a picnic? Can we sit on the same blanket or will you take that the wrong way?

6 Responses to “The Other Side”

  1. […] a Good First ImpressionFree Stock Photography Guide to Help Sell Your Photographs Online …The Other Side « A Frum PunkMaking Eye Contact | Attuworld.comBuild your Flash Intro | Online PublishingBuild your Flash Intro | […]

  2. Great post! There is a lot going through your mind!

  3. My daughter likes Weird Al, but she’s only in 11th grade so she’s not available, sorry.

  4. i don’t think you should think at all before going on a date. just go as you are and be what you are. don’t say much about yourself just let her speak. the rest will follow.

  5. Where does she want to go?
    Probably to the kitchen where she can cook.

    What should you wear?
    A wife-beater and shorts.

    How much can you spend?
    You’re giving her the honor of going with you, she should pay.

    Where to look?
    Like Peter Griffin said, “Why do women have boobs? So you got something to look at while you’re talking to them.”

    Music in the car?
    A porno soundtrack so she gets the right idea.

    What do you talk about?
    Don’t talk while you’re eating, bad for digestion.

  6. Never wear white pants. Ever.

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