Dating Questions?

Gila is collecting dating questions. Not the “tell me about your siblings/job” type of questions, but something more interesting that will help you get to know your partner better.

Now, I’m guessing she doesn’t want “If you were dumped on a desert island what five books would you want to have along?” type of question. They sound horribly awkward when they’re trotted out on dates (I know from experience) and anyway, I don’t think they’re as telling as they’re supposed to be. If I was going to be abandoned on a desert island I’d probably want “Desert Island Survival for Dummies,” “Home Desalination Made Easy,” “101 Recipes from a Palm Tree,” “The Boy Scout’s Guide to Being Rescued at Sea,” and “1001 Games You Can Play Alone.”

Now, if I had to choose five books to take on a boring vacation with me, the list would be rather different. And I can’t tell you what would be on it because I’d want books I haven’t read yet and I don’t know what I won’t have read by the time the vacation happens.

But anyway, every time one of my dates has used one of those questions (“So, if you could live anywhere, where would you want to live?” Dunno, that’s not an option I’ve ever thought about, seeing as it isn’t very relevant.) it has positively jarred the conversation. Probably because they’re always thrown in when things are slowing, have zero relevance to anything else in the conversation, and just don’t sound natural.

So please send Gila your questions, and post them below as well. And do us all a favor and make them natural sounding, the kind you can slip into a conversation without sounding like you’re trying too hard.


25 thoughts on “Dating Questions?

  1. Actually the answer you posted to the books question is very telling. Some of what it says about is not really that important from a shiduch perspective, I think, but others are. In fact, it sounds to me like you have one of the crucial traits for a good spouse πŸ™‚ – The ability to deal with what life hands you. You sound quite practical minded, even though you are also clearly a reader. I know that anyone who reads this blog would know that already, but remember, your dates officially haven’t read your blog.

  2. Both of those links go to the same place. Should “Gila” link to somewhere else?

    Your question really applies to any kind of meeting between two virtual strangers. The goal is the same – you’re trying to get to know them better.
    In that vein I like to ask something along the lines of “What interests you? What are you passionate about?”

    Usually people find it quite easy to talk about what they’re really interested in, it tells you a lot about them, and you can usually keep up a good conversation
    with a few choice questions.

    As far as being too obvious, well the point is to get to know them. You don’t have to do it in secret.

  3. any one of these types of questions will sound awkward bec they don’t come from a flowing conversation. even if the conversation is going this would just break it up.

  4. β€œWhat interests you? What are you passionate about?” I think this one is great. You should be able to tell if the person is faking it with just a few qualifying questions.

    it doesn’t have to be “awkward” you can make a game out of it. Just say, hay let’s play 20 questions. I did it with all of my dates… including my current wife. I don’t think I ever got to the full twenty before I made a decision one way or another. With my wife I made it to like 12, at which point I decided that I would move heaven and earth if necessary to marry this woman. With one date it ended at the first question so fantastically that I put down $200, and said, “I am so sorry, but this is just not going to work, have a great evening.” Then I left.

    I will have to dig up what my core questions were… I probably still have them in a file somewhere.

  5. “If you were on a date and there was an awkward silence, would you be uncomfortable with it?”

    “If you were on a date and there was a lul in the conversation, would you ask a trite question to pick things up again?”

    “When you are on a date, do you worry what the other person thinks about you, or are you so genuinely interested in your date and who they are as a person, that you naturally have no space to worry about yourself?”

    Bad4’s Wise Older Brother

  6. At the risk of sounding shallow, I think the type of music a person listens to says a lot. There’s a difference between Carlbach lovers and Gad Elbaz/Chaim Yisrael types. But usually I can guess the music type without even asking.

    On a related note (to your blog post), the best question to ask would be “Where would you send your kids to school?”

    This can be asked when gathering information pre-date, or saved for a more serious date. Either way, it says a lot about the direction a person is heading in life and where they see themselves in a few years.

  7. I’ve never tried one of these (thank G-d I’ve never had to), but I can’t help feeling like good4nothing – if it’s so obviously one of those questions, I can’t see it helping.

    mekubal: $200!! On a first date?!

    Best4: Those are awesome.

    MCP: I had to google that. I guess I’m not a keeper.

  8. Aminspiration- Right answer =)
    Male- Considering that i assume “male” identifies you by gender and not as some girl who’s parents have a horribly mean sense of humor, it’s safe to say that you wouldnt be a keeper in my book anyways

  9. I think my response to a lot of those questions would be “It depends.”

    “Where would you send your kids to school?” – I don’t think hypothetical kids should be mentioned on a date. While of course it’s about marriage, it doesn’t have to obviously be about marriage.

    I’m actually interested in another’s background and siblings – you can tell a lot about a person in terms of where they’re from, their location in a family, how many brothers and sisters, and so on. I even like it when they chat about grandparents – I go by the premise “If you don’t know where you come from, you don’t know where you’re going.”

  10. When you take the dumb hypothetical questions to a level of utter absurdity, they can be fun, as opposed to stilting.

    Like –
    “If you were auditioning for ‘The Princess Bride Goes to Yeshiva’, would you be Inigo? Westley? Fezzik? Buttercup? And why?”
    (ps – if the dude says he’d be Buttercup, he better dang have a good reason)

  11. aminspiration- definitely! I wouldn’t hold it against her if she didn’t have the right answer, but she would get mad points if she did lol
    Male- true that, must have been the inner chauvinist in me putting guys first πŸ˜‰

  12. Put 200 bucks on the table and leave?

    I am sure you are joking!

    That’s really, really insulting. I would feel like a prostitute if a guy did this to me.

    At least you could have had the decency of discretely paying the bill and leaving.

  13. How about “what was the most interesting job interview question you were ever asked?” Tee hee.

    Or depending upon what you know about their work background the question could be more like “Have you ever had a job you had to interview for?” or “What’s a good job interview question that you like to ask?”

    Of course I could see getting hit back with a very technical topic just to spite me…..

  14. Wouldn’t be so sure that the question “So, if you could live anywhere, where would you want to live?” is just a dumb throwaway one. Might be a bid to find out if you are “married” to Brooklyn or perhaps NYC or if you would be amenable to moving elsewhere. When I was redting shidduchim I had plenty of men and women who turned down a further date because it was clear that the other person had no intention ever of leaving NY or it was clear that the other person had every intention of leaving NY.

  15. β€œYou are male, right?”

    Of course. Everyone knows that women are analphabeths and would not need to take any books to a desert island…

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