Browse > Home / Dating and Mating / Blog article: Best Questions To Ask A Date

| Subcribe via RSS

Best Questions To Ask A Date

August 4th, 2006 Posted in Dating and Mating

Yesterday. I’m at my temp job. And, I’m talking to my coworker & friend Asia about my upcoming date with Sven Johånn Låårssøn . (No, she’s not Asian but her name is indeed Asia.) Asia’s worried that I’ve been out on several dates with Sven and I haven’t asked certain key questions. “So, what’s this guys’ story?” she asks. But, I don’t know what she’s getting at, so I answer her question with another question: “What do you mean?” She seems surprised. “I meeeean,” she says for emphasis,” “Is he married? Does he have a girlfriend? Kids? A job? … You know, what’s his story?”

Call me a Midwesterner, but I ignorantly assume that the guys that I date are not married. So, I’m kind of embarrassed when I tell Asia that I haven’t actually asked Sven if he’s married. “Girl,” she says, “you gotta ask them if they’re married. Otherwise, they can always say, ‘you never asked.’” One of my friends in Chicago vehemently subscribes to the same philosophy: assume they’re married unless they specifically tell you otherwise. But, she got burned once. And, it was bad. So, now she not only asks men if they’re married, she also asks, “Is there any woman anywhere who has any reason to believe that she is (or could possibly be) your wife?”

Hmmm … I guess there are certain questions that you should ask every date. But, it’s not like I’m husband-hunting or anything; so, I figure the first few dates are just supposed to be about having fun. Sure, we’ll eventually get down to business and talk about the heavier stuff like “what’s the longest relationship you’ve ever had” and “why do you think your last relationship failed”— but that comes later. And, now that I think about it, “later” is “now”; it’s probably time to start asking Sven the heavy questions. Hmmm … What about you? Do you have any specific questions that you’re always sure to ask a date before you decide to get more seriously / romantically involved?

16 Responses to “Best Questions To Ask A Date”

  1. AWE Says:

    Can’t think of any questions right off hand.

    I finally found out what that sign meant. I saw it one day driving around town and had no idea what it meant, now I do.


  2. Howard Says:

    Yes, I do have a couple of deal-breaking questions that I usually ask upfront so we both don’t waste our time. Stolie, apologizes up front for making this heavier than I usually am:

    Are you comfortable dating someone who is HIV+?

    You wouldn’t believe the fear, ignorance & prejudice that is STILL out there within the gay community.


  3. hotdrwife Says:

    When I was single, I got burned pretty good – the guy was still married, somewhat not-together, blah, blah. In fact, that guy had a LOT of things hidden, and questions I didn’t even THINK to ask. The more I think about it, the more I’d like to stomp on his face for good merit.

    So, needless to say, I stopped dating for a while after that.

    That would be my question if ever in the ring again.


  4. Pegs Says:

    I have two mandatory first date questions, delivered with just a hint of humor, except that I couldn’t be more serious.
    1) Have you ever been married?
    2) Do you have any children?
    This is not to say that if he answered “yes,” all bets would be off. It’s just that there’s never a good time to bring those yeses up, so I give (gave) him the opportunity right away.


  5. Mitch Says:

    Hey Stolie,

    Best questions to ask a date?

    I never really specifically set out to find out the information – but my job as a meeting facilitor almost brings it out naturally.

    Usually by the end of three dates I have the basic information that I already know or need to know.

    namely associated with baggage (kids, married etc) nasty exes, their ability to trust, career drive etc.

    It all comes out of the conversation over the first few dates to me… but I don’t seek the questions outright.


  6. Laurie Says:

    These questions are not up there with are you married/got kids/a serial killer, but some things I ask most people I really want to get to know:

    What makes you happy and when are you the happiest? (the answers can be shocking at times)

    What makes you angriest?

    Do you like animals and if so, what kinds? (I’m an animal person so I’m always very interested in the response. I don’t trust people who don’t like animals at all.)


  7. Nics Says:

    You’re not from Armagh, are you? I jest. Can’t think of any to be honest. I think that if I were going to date someone older than me I would ask about prior relationships and children etc.


  8. MamaChristy Says:

    Well, it’s been a while, but I always got around to the idea of marriage and children within the first three to five dates. That was something that I wanted and I wasn’t going to waste my time with a guy who didn’t want that. I was also looking for a man who was Christian (demonimation didn’t matter to me) but wasn’t a complete prude.

    Awe – what does that sign mean?


  9. goldennib Says:

    I think the, Are you married or in any form of committed relationship?, a question that needs an answer before going on a first date.

    I prefer not to associate with someone who can not honor such a basic agreement.

    A date is not the same thing as a simple social get together.

    All other questions can be answered based on how the relationship goes.


  10. stolie Says:

    AWE: Yeah, I can’t be 100% sure, but I think the sign really does mean something about “dating questions”. ;)

    Howard: Wow, thanks for sharing and for being so honest!! And, about that fear / ignorance / prejudice in the gay community … I would venture to say that it’s probably the same in the straight community as well. Random sidenote … Boy#2 was the first guy to ever ask me, “So, when is the last time you were tested?” I was so naive that I honestly asked, “Tested for what?” We had a serious discussion about how anyone who is sexually active should probably get tested. In the end, we never slept together but I think it’s great that we got tested. (And, not that it matters, but “negative” in case anyone was curious.)

    hotdrwife: Yeah, my friend got burned too. She asked the guy if he was married and he said no. Later, she found out that the whole time she dated him, he was seperated and in an on-again-off-again thing with his wife. Hence, she now asks: “Is there any woman anywhere who has any reason to believe that she is (or could possibly be) your wife?”

    Pegs: GOOD questions!! :)

    Mitch: I’m naturally a very curious person. So, I usually get around to asking the tough questions — just later rather than sooner. :) … By the way kid, I have something that I’ve been meaning to stick in the mailbox for you for quite a while now. I’ll do it today or Monday. Sorry for the delay.

    Laurie: I *LOVE* your questions. Very light & happy.

    Nics: It’s true, the older the date, the more likely it is that there may be prior marriage(s) and/or kids. Every situation is different, but I would *prefer* to date a guy who hasn’t been married previously and does not have children. But, you never know because … ya know … Paul Walker has a kid (kids?), and I certainly wouldn’t ever bar him from entering my vagina.

    MamaChristy: That’s really cool that you knew what was important to you and you were unwilling to compromise.

    goldennib: Good advice. And, I think I do kind of see dates as social get togethers in the beginning. If things heat up and I decide that I like the guy, then the date questions come. Good news is that I often become “friends” with the guys who things don’t heat up with, and we never have that awkward “I used to date him” feeling. The bad news is that some guys (like, for example, Le Canadien) freaked out when I switched gears and got more serious. ‘What’s with this serious stuff now? I thought we were just, you know, having fun.”


  11. stolie Says:

    Oh yeah, by the way, I had another great date with Sven (and I asked the hard questions). So, yeah, so far we’re on a winning streak. :)


  12. Howard Says:

    Hooray! I’m glad I came back here and read your good news!


  13. Pegs Says:

    Yippee!


  14. Darwin Says:

    I guess the married/kids question. I suppose I’m quite naiive but I expect that to come up during the course of the conversation really! Also, again I naively don’t expect married guys to date other people!


  15. momok Says:

    Hmm… I wouldn’t directly ask anything, but I really want to know if I can have an intelligent conversation with her (besides other things, ofcourse).
    Instead of asking “on a scale of 1 to 10, how smart are you..”? I’d ask about things which gives me an estimate.

    And whats with “/*”????? What does that mean?


  16. stolie Says:

    Howard: Yeah, so far, it’s been really nice. It’s still fairly new, so who knows what (if anything) will develop. But, for now, it’s really nice & I’m happy.

    Pegs: THANKS! :)

    Darwin: Same here. I never really think to ask it, because I assume: hey, if this guy was married with kids, wouldn’t he tell me that?!?!. Sad, but it’s not really an assumption to be made these days.

    momok: You’re right: it’s odd, but things do seem to come up fairly naturally … And, by the way, what do you mean by the “/*”. Did I say “/*” somewhere? :)


Leave a Reply