Solely In Black and White: Top Ten Interesting, Conversation Starting, and possibly fun Dating Questions:

Friday, July 30, 2010

Top Ten Interesting, Conversation Starting, and possibly fun Dating Questions:

As a means of providing a few ideas for Gila’s dating question collection (and also in place of commenting on Bad4’s post) I made my own Top Ten List. This list of questions should foster a formidable discussion on a date. I have tried most of the questions with varying levels of success, but for the most part, they can provide some food for thought. If you’re feeling extra comfortable with your date you can even “respectfully and in good taste” have a full-fledged debate! That is unless you both choose to answer these queries solely as “yes” or “no.” Then they might not work so well. If all else fails, you can always ask your date what their favorite blog is, but thankfully that question never yielded the answer I was looking for…. :-P ;-) 

1. Is it easier to be a “good boy” or a “good girl?”
2. Do you believe in the Shidduch Crisis?
3. Do you believe that aliens exist?
4. If you could be any superhero (or as a variation of this question, character from a book or movie) who would it be?
5. What is the craziest/oddest/strangest food you have ever eaten?
6. If you won the lottery, what would you do with your winnings?
7. What are you looking for in a spouse? (For those who prefer to avoid referencing marriage on a first date use the variation: what attributes do you value in a friend?)
8. If you could go anywhere, where would you have your ideal vacation and what would you do there?
9. What is your favorite childhood movie?
10. The last one involves asking a hashkofically inclined question which can lend itself into a discussion. I don’t know if this idea is prime first date material, but depending on the situation it might work. There are many examples, some better than others, but I am actually curious what you think about this particular, albeit random, peculiar, and quite morbid, question: Rachamana litzlan, if one is presented with a situation where they have a closely related family member in front of them who is slowly dying, wherein the end is imminent, can said person daven and request that Hashem hasten their relatives death in order to alleviate their relative’s pain and suffering? 


  1. woo hoo! first comment! ::does first comment dance:: I like all of the questions listed..though some are a tad more risky than got guts Mr. SIBW...that's for sure. I especially like the aliens and superheroes ones...yay! :-)

  2. my fave besides the obvious one that was my idea to begin with is the one abt believing in the shidduch crisis or not..and thats another good idea to post abt..wether it exists or not..

  3. @mmmmchocolate :-) :
    I may have guts, but would you answer all of the above questions on a date? :-)

    Agreed. Those seem to have worked well.

    Yes, that does make for a good discussion topic on a date and maybe even for a post. Although it has been blogged about quite a lot….

  4. hmmmm- i think i actually have answered 90% of those questions at one point or another in my dating career.....

  5. @mmmmchocolate :-) :

    And in your dating experiences, do you think these questions are worthwhile?

  6. I'd rather not feel like I'm in a psychiatric interrogation on a date. Why can't it just flow? I don't think I have answers for most of these questions (although I am firm in my belief that there is no shidduch crisis, and my favorite superhero is Batman, but I wouldn't want to be him or any other spandex-clad hero because there's too much responsibility and I probably couldn't handle the guilt).

  7. Data, what if you didnt have to wear the spandex, would you feel less guilt?:p

  8. Sorry I don't like any of your top 10 questions reason being is that you seem to conduct dates like interviews. Hellooooo...until you get the idea that dating is not conducting an interview GOOD LUCK. Your date is going to be plain and simply boring AND it's going to be so rigid and formal. Forget the fanfare and pretend you're meeting up with a friend. Just be on your best behavior (aka manners).

  9. @Data:
    I know what you mean; these questions are slightly psycho-analytic based, but then again that’s an interest of mine and possibly why they worked for me. The questions don’t have be asked in an integration style, they can also be used as conversation starters, because there isn’t an absolute right answer to most of those questions and it’s fun to see how people deal with them… such as your response to the shidduch crisis question and such…. :-)

    So what topics do you recommend someone should broach in order to have a free flowing and natural conversation?

    Why, who or what would you choose? ;-)

    @(not) The Girl Next Door :
    Okay, to each their own I guess… Not even question one and two? :-(

    Aha, but the difference is that I know what interests my friends and what topics they enjoy talking about. But when you meet a complete stranger conversation doesn’t always flow so nicely for a few reasons obvious reasons. There is a known phenomenon called awkward silences for a reason. ;-) What I enjoy most about those questions is that they can be approached from many aspects and view points, humor included. :-) It’s not about giving a correct answer to the interviewer but fostering a discussion.

    As I asked data above: So what topics do you recommend someone should broach on a date in order to have a non-rigid and informal conversation?

  10. I like silences. I find them companionable, not awkward. Also, if the guy is not being chatty out of sullenness, my going silent makes him suddenly open his mouth.

    Would I feel less guilty in sweats rather than spandex? Not likely. And according to Edna of the Incredibles, "NO CAPES!" Plus a superhero died in Watchmen like that. What's the fun if I can't have a cape?

  11. data-the cape isnt made of spandex, u cud fly and eat your cake too (without the guilt if ur wearing sweats:p)
    SIBW-i fancy myself wonderwomen so thats my obvious choice tho im not so into the superheros myself..besides the costumes dont exactly follow the the halachic guidlines for tznius..:p


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