What a Woman Should Never Ask on a First Date (Unless She Wants to Die Alone)

I recently contributed to “Advice Uncensored,” a section of SavvyMiss.Com, for No Holds Barred advice for women. The question this week is “What Should You Never Ask on a First Date and Why?” You can read my response below. I felt the readers deserved some “less than traditional advice”:

When getting to know your date, it is important to utilize open-ended queries that allow him to reveal his personality. Avoid close-ended questions or those that have a forced choice. Better, “Tell me about the last stripper you dated,” than “Are looks important to you?” With the former, you are creating a format for an open dialogue with description and insight into your date’s preferences and dislikes. With the latter, you are pinning him down to a simple “yes/no” response with little to no room for expansion.

Of course, the content is as equally important as the style. As we all know, there are certain taboo questions on first dates: “How much money do you make?” or “Can you meet my parents tomorrow?” and “Don’t you hope I’m ovulating the first time we have sex? You know, about 11 months from now?” are all deal-breakers. These questions demonstrate shallowness, poor boundaries and prudishness, respectively.

Additionally, asking questions about topics that are unfamiliar or undesirable to the average man is ill-advised. “What brand of tampon did your last girlfriend use?” and “Which episode of The View last week was your favorite?” are examples of poor questioning.

They say never to discuss religion or politics in polite company. Beyond that and keeping in mind both style and content, I would avoid questions such as these, as they violate all the laws of good conversation:

“I don’t enjoy sex or sports, so would you rather spend today knitting a blanket or simply crocheting a shawl?”

“You don’t like beer do you? Because in our family we are only going to drink water.”

“How much are you going to spend on my engagement ring?”

“I have an excessively long menstrual cycle and refuse to take Motrin. Is this a problem?”

See how easy it is to make a good first impression?

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8 Responses to “What a Woman Should Never Ask on a First Date (Unless She Wants to Die Alone)”

  1. Blank says:

    Lmao, how did you come up with some of these questions? I hope to god you don’t say through experience, eheh.

  2. Liz says:

    interesting, though I note you don’t put in a difference in conservative beliefs and prudishness….

  3. missmephy says:

    AHAHAHA. crocheting isn’t simple, though. far from it. otherwise that beanie i started making last year would be finished now.

  4. Jake says:

    Oddly enough, I find that I myself am able to expand upon questions that are even a bit narrow. Perhaps I just like to hear myself talk, or something like that, but it annoys me when people will take questions and give short “yes” or “no” answers no matter how simple it would be to go in depth about the question, or at least briefly explain your answer.

  5. christina says:

    Well I read your article on what not to say on the first date. First it was absolutely brilliant! Second I went on a date with someone about a week ago and it wasent going well so I asked him “How much money do you plan on spending on my engagement ring?” Hoping like all hell that he would back away and I wouldn’t have to be the one to end the date. He actually responded “Well I make about $2000 a month and they say you are supposed to save up three months worth so I guess $6000.” Holy hell! I told him that I didn’t think it was going to work out between us and backed out of the restaurant slowly and left.
    So essentially your plan backfired! Thanks Dr. Rob. Your a super friend!

  6. Shady says:

    You don’t look like a felon in the picture, you’re actually pretty hot…especially for a 35 year old.
    You look like you’re in your early-too-mid twenties.

  7. David says:

    Dude, you’ve gotta learn to smile for the camera. It’ll cut down on your felon vibe.

  8. Lidia says:

    I TOTALLY agree with Shady!!!
    It’s a big bummer you’re not early-too-mid twenties…
    You’re breaking your young fan hearts..

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