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First Date Questions

January 18, 2012

Looks like he likes her and she's laughing. I'd say someone just asked or answered a good first date question.

So I’m going on a date tonight and I’m actually excited about it. And it’s been a long time since a guy asking me out was someone I was actually interested in getting to know better. In fact, over the past few months (maybe years even) the biggest reason most of the guys got a shot is because I didn’t want to accidentally turn down someone who could be the guy just because he didn’t seem very interesting initially.

At least looking back that’s how it seems. I mean, to be fair I was excited about the professor for most of our first date. Until I found out that he wasn’t interested in a “monogamous, long-term relationship.” Great.

That’s right, he told me on like our first date that his plan was actually to date me (and have sex with me) and date several other women — one whom he had already chosen — and sleep with them as well. Now, I’m not a guy, but if dating a girl (and sleeping with her) makes you want to sleep with other women she’s probably not the one — and she probably isn’t very good at sex either. I’m just saying.

And the funniest — and perhaps most tragic — part: I still went on like four more dates with him. I don’t know what I was thinking. Although, upon retrospect, if I had stuck it out one more date maybe he would have fixed the overhead light in my living room like he promised. I wonder if it would have been worth it.

Well, at any rate, I have a first date coming up. That’s my point and I’m excited about and I guess that made me feel like sharing. So, I thought I would commemorate the event with a little participation from the audience. I’d like to know what you all think are good questions to ask someone on a first date. Male or female, but maybe if it’s a gender-specific question let us know.

And I don’t want all of the silly little pedantic things that will come up naturally. I mean good questions that could possibly reveal important things about this guy. (You know, like how many women he plans on sleeping with at any given time.)

For example, I used to always ask, “What do you want to be when you grow up?” And that was usually fun and informative — even once we all became grown-ups (sort of). But with this fella something makes me think it will be out of place.

I also used to ask fellas a two-fold super-hero question, “If you were a superhero, which super hero would you be and why?” And, “If you could be any super hero which super hero would you be, and why?” It seems like the same question for some people, but the nuance is important. The first identifies which superhero the fella is most like currently and  the second identifies who he would want to be. It can be a great conversation starter and also reveal interesting things about a guy.

For example, a fell who is most like Batman might have issues with the amount of money he spends on big-boy toys like cars. Not that that’s always true, but it has some relevance.

Again, I’m not sure if those questions will work on the fella I’m going on the date with tonight. But I might try them anyway. (Folks, I’d say the super hero questions are probably better to ask a guy unless the particular lady you are on a date with is clearly into that sort of thing.)

Also, last night while I was getting into my pajamas it struck me that the moment I take off my bra is almost always one of my favorite moments of the day (damn you under wire!) and I think it might be a good idea to ask a date (male or female) what their favorite part of the day is and why.

But…really, that’s all I’ve got for now. So I need some more questions if I’m going to conduct a worthwhile interview over dinner tonight. HELP ME OUT!

(I wonder if her would be weirded out if I take notes? Yeah…probably. Drat!)

14 Comments leave one →
  1. January 18, 2012 3:06 pm

    Well I always like to say if you can’t dazzle them with brillance, then baffle them with bullshit!


  2. Tanya permalink
    January 18, 2012 3:40 pm

    I don’t think I have any shards of brilliance to share to make your date better. But I did think the paragraph starting with this line was, to use your words, funny and tragic. Love it! “And the funniest — and perhaps most tragic — part: I still went on like four more dates with him.”

    Anyway, have fun tonight.


  3. dave c permalink
    January 18, 2012 8:25 pm


  4. Just Saying permalink
    January 18, 2012 8:34 pm

    hahahah I take my bra off the minute I get home! The puppies say “aaahhhhhh”.

    Good luck on your date! Let us know how the questions go!


  5. January 21, 2012 11:39 am

    I really enjoy reading your blog! Looking forward to hearing how the date went…..oh, and taking off my bra is my favorite part of the day too…well, one of them anyway 😉


  6. February 6, 2012 11:31 am

    As a married man, I always appreciate the bra removal by my wife too, a daily highlight. 🙂

    However, on topic:

    Mountains or sea,
    Books or films,
    BBQ or Kitchen,

    Any choice tells something, just depends on what you want to know in advance.



  7. December 12, 2012 8:22 am

    When life matures and you’re ready to ask the questions that will land you a man of quality, let me know.


    • December 12, 2012 11:15 am

      Chris, do you see how that is a rather back handed insult? It implies that I am immature and unaware of it. And I certainly want to know what questions might lead me to a “man of quality.” Otherwise I wouldn’t have bothered writing about it or asking about it.

      So, please, if you are so much more mature than all of us (or at least me) can you share and help us get to that next level instead of just telling us how below you we are? Please?


      • December 12, 2012 11:50 am

        I’m sorry, wanting to know what is their favorite color, book, movie… is, then that’s the quality of relationship you’ll get. However, if your ready to dive deep and explore a more meaningful relationship, it’s time to ask different questions.
        On my site I have 3 pages that addresses this issue: Boundaries and Personal Power, Manifesting Ones World, and Relationships. However to answer your question more directly.
        When you meet him and before you decide to go on your first date, ask him one question, ask him how he ended his last relationship, and you will know just what kind of relationship he is capable of giving. So if he was insensitive in his last break-up, he will be insensitive with you. And therefore he is not for you, it’s really just that simple, and no, he’s not going to change. He may change what color socks he wears, or what kind of car he drives. However personality traits take a long. long… long time to change. If he says he will change for you, it’s faults and he will change back.


        • December 17, 2012 8:31 am

          Chris, I think you are being a bit myopic here. It may be useful to know how a person’s last relationship ended, however I don’t think such information is ever truly available prior to a first date. Setting aside the fact that it is rude to ask about such things before a certain point, you also need to consider the fact that most people who are deeply flawed are not aware of thier flaws. Even those who are are unlikely to be either willing or able to express those flaws — especially to someone who is a prospective romantic interest.


  8. December 17, 2012 9:11 am

    If you want a relationship that’s deeper than a puddle, you’ll need the courage to venture into those dark corners and challenge those old ways of thinking… you’ll need to challenge the way you see the world. If you want to play it safe, then you will continue to have the quality relationships you’ve been having.
    When you say “it’s rude to ask such things before a certain point”, who’s rules are you referring to, are you referring to those who are deeply flawed? Are you looking to have a relationship with those kind of people!? Or are you ready to think outside of the box? To change the quality you want, you will have to believe that you deserve. And once you create such trust within yourself, you will not only have courage you will have the integrity to ask any question of any person at any time.


    • December 17, 2012 12:16 pm

      If someone I did not know well, or whom I was on a first date with (and generally on a first date people are virtually strangers in my culture) asked me how my last relationship ended I would say he broke up with me and I’m not completely sure why. I tried to find out, but it I didn’t find out much.

      I really think that if you don’t know someone rather well already you won’t get much of an answer to that question and any answer you get will be put in a way that makes the person you are asking feel good about themselves.

      Now, as I said I was putting aside the fact that I find that question rude and I believe a lot of people would — especially before a first date.

      Aside from that you didn’t really provide much insight about what a person might learn form the answer to that question. Also, I find your comments to be generally snarky with me and I’m on the verge of blocking you from commenting on my threads at all.

      Your last comment suggested that I am “playing it safe,” have low-quality relationships, can’t “think outside the box” and that I lack courage and integrity. Can you see how cruel that seems? Can you further understand that no matter how good your advice may be, insulting someone as you try to give it negates any power you may have to make your point?

      You do not know me, except perhaps through the posts on this blog. And I assure you I am not my blog. This silly collection of my thoughts is not all of who I am nor the sum of who I will become. Please do not judge me based on it’s contents. In fact, I’d appreciate you not judging me at all.

      I do appreciate you offering a suggestion for a question to ask someone I may date or be dating. But in the future, please do not speak (write) to me — or any of the other people who comment on my blog — as though I am below you in any way.


      • December 17, 2012 6:50 pm

        I’m sorry if I offended you, it appears the circumstances that surround me are very unique and blessed indeed. My intention was not to put you or anyone down, some people need to be shaken a little to be wakened. I will let you go now.


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