Death to First Date Questions

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Once upon a time, long long ago, there lived…a great date.  This great date was nothing like the dates of the 20th century.  It was magically engaging; complete with great conversation of substance and quality.  New acquaintances were excited to go on these dates, for they truly wanted to get to know each other!  So they asked questions…questions that mattered…questions that would unveil their many secrets and truths…questions that could one day lead to a promising future.

But one dark and gloomy day, a wicked and terrible disease named “Self-Interest” crept into the dating scene.  It spread like wildflowers; quickly becoming the most horrific and damaging of all dating diseases.  Before anyone could stop it, questions of substance were suddenly replaced with phony filter questions.  Attempts to learn each other were dangerously replaced with attempts to take from one other.  Dating became tragic; a frightening and disheartening disappointment to many remaining singles.  Sex and manipulation were now the name of the game.

Fed up and frustrated, many of these singles just threw in the towel.  It was pointless!  Dating had become nothing more than a ploy for a free meal or a cheap thrill.  But one day, right when all hope seemed to be lost, a beautiful BADA$$ Queen named Nosie Josie swept down on the desperate singles and delivered what could very well be the answer to their lonely prayers!  A dating cheat sheet of:

1st Date Questions to Erase & Replace

Syke!  You guys remember that word?   Seriously though.  One thing I’ve learned this week is that what might come off as a horrible date question to one person, may seem ingenious to another.  So I won’t be making that list – not today at least.  We are all just way too different to share the same sentiment as it relates to our dating preferences.

Me?  I’ve unwillingly come to the conclusion that my way of thinking is a bit…different than most.  Its not on a higher plane per se (although I’m willing to roll with that if you are).  Its just on a more intricate one.  Thinking on a surface level has never been my forte. And trust me, for my own sake I’ve tried.  I just can’t subdue my overthinking in an attempt to find satisfaction in superficiality.  Doing so almost always results in a sort of word vomit volcano eruption for me in the end.  And boy does that get messy…

In all honesty, this superficiality trend is a major reason why I don’t date much anymore.  Its not that I don’t have offers…I’m just pressed to find conversations that don’t annoy me actually stimulate me.  Is it my fault that I’m bored with the usual filter questions?  You know, the typical 6 questions we ask on every first date.  The ones that that turn our new and fun experience into a screening process:

#1 | Do You Have Any Kids?

I feel like this question almost always goes south unless you are both childLESS or childBLESSED.  And we have the audacity to LEAD the date with this question, most times!  If you have kids- chances are, you’re making sure I’m okay with joining your ready-made family.  If you don’t have any kids -chances are, you’re making sure I don’t come with one of my own.  Both points understood…and valid.  But awkward for me nonetheless.  Why?  Because now I feel obligated to follow up my “no I don’t have any kids” with a “do you?” Which (if you have kids) ultimately pressures me to confirm on the spot if I’m okay with you having them.  I’m looking at you…you’re looking at me…


What am I to do?!  If I come back with a followup question, it suggests that I’m on board.  If I don’t, I come off as disinterested and rude.  You’ve put me in quite a pickle, haven’t you?!

#2 | What Do You Do For Work?

The only people who ask this question are those pricks who enjoy what they do for a living.  Or those who don’t and want to gauge if they can sustain off of your income instead.  And before you try to convince me that you’re just curious about how I spend my day…don’t.  I spend my days at work, in turmoil and mourning my freedom like most of America.  I promise you that I won’t subdue my green-eyed giant as you boast about how awesome your career is.


And if this is just your idea of a conversation starter, there are much more creative avenues for you to take.  Try asking me ask me what I do when I get OFF work.  Better yet, what I would be doing with my life if I didn’t have to work.  Ask me if I feel like college was worth the investment.  That way I can at least rant about Sallie Mae owing me a refund for my dormant degree.  That’s what I want to talk about.  You’ll be sure to get to the heart of who I am with that one.

#3 | What Are Your Career Goals?

Not flipping desks over.  Not doodling.  Not stealing someone else’s lunch from the office fridge.  Showing up on time.  Perfecting the art of “2-for-1” with the office vending machine.  Breaking through the office firewall.


Mastering the ‘Alt-Tab’ method.  Securing a work-husband.  Looking awake in my cube after a home visit with my work-husband.  Not becoming the subject of office gossip when Chatty Chelsie realizes I spent the night with my work husband.  Seriously though…sometimes I feel like we forget there’s more to a person than what they do for a living or how many degrees they have.  I’m more than my career (for the sake of humanity, I pray that I am).  In fact, I have 31 years of awesomeness that I can share with you if you ask the right questions.  Focusing on my career forces you to miss out on all of the good stuff that truly make me…ME.  I would much rather you ask me what my PERSONAL goals are.  For the love of God, let this date uplift me!

#4 | What Happened With Your Last Relationship?

Because that’s exactly what I want to talk about with the untainted, new man sitting across from me – what scared the last one away. Seriously though, I don’t know too many people who enjoy rehashing their past while making efforts to move on from it.  Can we talk about something more pleasant and relevant?  Like how great this wine is!  Or who’s next to die on The Walking Dead.  Because if we start talking about my ex, my mood might very well drop from hero to zero – and then we’ll both need a drink.


Truthfully,  no one wants to hear someone talk bad about their ex.  Even if you have valid reason to gripe.  They want a cookie cutter response; one which shows that you can own up to your part in the relationship failing.  And not everyone is ready or capable of doing that just yet.  There’s also a strong possibility that my last relationship didn’t end on bad terms.


Yes…I may still consider my ex a great fit for me – just with bad timing.  I would hate for you to spend the remainder of the date questioning the possibility of us getting back together.

#5 | Do You Smoke or Drink?

If this is your way of finding out what I do to unwind or relax, I would suggest you just ask.  Because just asking this question leaves me wondering whether you’re a lush or a pothead.  Or if you’re anti both – which opens up an entirely different can of worms.  Will your idea of a fun date consist of Madden smoke sessions?  Or will you instead be giving me the side-eye whenever I pull out my wine bottle?  Because if either is the case, just kill me now.


#6 | Why Are You Still Single?

The most horrid of all interview date questions.  If for no other reason, it burdens me with trying to figure out a justifiable answer that’s not a total lie.

What could possibly be a good answer to this?  Because if I tell you that I enjoy being single or that I am not pressed for a relationship, you’ll question why I’m even on the date.  If I tell you that I suck at dating or relationships, I might as well decorate the table in red flags.  If I tell you that every man I meet is crap, I’ll sound difficult and full of myself.  The only good answer is probably a lie and will most likely sound like I’m dodging.  Or there’s always the possibility that my answer will turn into a rant about my past experiences…and who really wants that?


You’re in awe at how wonderful I appear to be – I get it!  You’re looking at me from across the table thinking “wow…how could anyone let this great girl out of their grasp?”  But lets be real here.  Anyone over 25 has been through enough experiences to know that there’s way more to a person than what meets the eye.  I have flaws like everyone else.  Obviously my flaws didn’t work well with the last guy’s.          

Not to mention, it carries the undertone that a relationship is a necessity rather than a bonus.  It falls right in line with “why don’t you have any kids yet?”, “why are you wearing those shoes with that dress?” or in my case “why do you stay in this neighborhood?”  People rarely ask questions like these in admiration.  And depending on the woman you’re out with, she may see it as somewhat rude or offensive.  You would do best to just file this question under the ‘caution’ folder along with “whats your age and weight.”    

What are YOUR least favorite 1st date questions?

  Nosy Josie

About nosy josie (88 Articles)
Josie is an aspiring writer living in Chicago Illinois, inspiring self-love through her own tragicomic life journey. Follow Josie as she details her collection of dating fails, life lessons and heart-to-heart confessions with her nosy readers.

38 Comments on Death to First Date Questions

  1. This was interesting…. 1,2 and 5 are a must ask on first dates…. Kids are a major consideration so I need to know… What you do for a living is a huge part of who you are..and drinking and smoking is another major consideration.. Career goals are not as pertinent on the first date and the others will reveal themselves in due time.. Great article

    Liked by 1 person

    • Thank you! I definitely love the idea of waiting for certain things to reveal themselves over time. Sometimes we rush answers that we should just wait for. Now -which end of the smoking and drinking spectrum are you on? The one where smoking and drinking is a MUST or a bust? lol.


  2. You were right, this post is indeed one of your best :D …I haven’t been on a date in a LOOOOOOOONG time, but I agree…all this probing biz needs to stop…relationships are really starting to feel like ACTUAL work, too many actors outchea! lol :)

    Liked by 3 people

    • Haha! I’m glad you enjoyed it. I literally had a blast while writing it – laughed most of the way through it. Dating has definitely turned into an interview process – and although I understand that in a way it is, I don’t want to FEEL that way while on one. You’ve gotta get out there before dating becomes a foreign process to you entirely lol

      Liked by 1 person

      • Lol I don’t think the dating scene is for me Jo…all i’ll do is scare people away…this other time a girl said i’m intimidating, borderline rude for the insecure hahaha….who knows, maybe one of these days :)

        Liked by 1 person

        • lmao borderline rude for the insecure?! That’s a heavy claim she made there. I can’t imagine you scaring anyone way – seriously. I think I need to shadow you on a date. Intimidating – I can see that. Any man who speaks as you do can be intimidating to a woman who isn’t comfortable with her own level of depth. #true story (yeah I crept a hashtag in there lol).


  3. Ugh first date questions. Hate them so much. I really hate the “What do you like to do for fun?” one. It always is so hard to answer for some reason.

    Liked by 1 person

  4. I just recently started dating a new man, and after a handful of outings, he has yet to ask ANY of these questions! Thankyajeezus!

    All these questions suck. They just make things awkward. They remind me why I have been single for awhile. They make me lose my appetite. They make me want to end the date early and go home to my sketch pad, books and laptop. Alone.

    Liked by 1 person

    • I LITERALLY laughed out loud when I read the word “alone” at the end. Yessss I feel you on this so much. The fact that you and your new guy have been on more than 2 dates and found OTHER things to talk about is amazing! I don’t think its that hard to do! Get to know me before you worry about my stats – that’s all I want. And don’t get me wrong – I understand that the stats are important too…but (IMO) we prioritize wrong. We’re more focused on filtering people out and THEN seeing if we like who they are afterwards. When in all actuality, some of those filter preferences may change depending on the individual’s personality. In my opinion, we should be focused first on seeing if we like their person and THEN seeing which stats we can make an exception for with this particular person.

      Liked by 1 person

      • Yes! I completeeeeeely agree! And people are quick to cut you off if they don’t like your answers……………. But, you don’t even know me.

        Dating shouldn’t be so sucky.

        Liked by 1 person

  5. And yes, yes you are a badass!

    Liked by 1 person

  6. Question #6, Why are you single? Well, I’ve got one better. You’re Still single?! That’s my favorite. No. My least favorite! Lol Those “Tell me about yourself ” Q&A will come. I like to ask conversational questions. For example, “If you had to describe yourself in one word, what would it be? And why?” I even answer the question myself! My answer is “Bright. I’m bright in the brains, I have a bright personality and I I have a bright smile. So, I shine!” LMAO How now brown cow! Lol It opens the door and before you/I know it, I know the answers to those 6 questions AND MORE!!!

    Liked by 1 person

    • Amen! I LOVE conversational questions; especially the one you suggested “describe yourself in one word.” How much fun is that?! And think of how much you can learn about me with that question. If we really stop worrying about filtering people out – we would be surprised to learn than some people are worth making certain exceptions for. IE – maybe I don’t mind you having any career goals just yet because I see that you are XYZ… we focus on employing partners rather than enjoying them. Not just in dating but even in relationships. -singing Michael Jackson- “time to make a chhhannnge”

      Liked by 1 person

  7. Great post… I think we really truly think the same. I usually hit a date, like ummm, damn, same questions all over again… It’s like, dang, how fast can we get through these question quickly? Most the time, it’s the dislike of starting over and over hearing the same questions if you choose to go on a date. I guess that’s why first dates may be like one of those things I try to avoid. It’s like can I get to know the out of the blue, lifestyle, fun, what makes and break you questions and answers, than the typical, blah blah, oh yea, me too, oh really wow, that’s interesting uninteresting same thing I just heard a few days ago trying to make face.

    Should these questions be asked, I guess sure… I feel like you can simply hand a person a paper, and say check off what applies and I read and we go from there… lol

    Liked by 1 person

    • lmao I wouldn’t mind bringing a form that has all of those questions and more. Then, when my date starts to ask them, I’ll say “I figured you would ask all this. So I took the liberty of filling out a form for you. Would you like to review it before or after the date?” lmao he would hate me.

      I agree with you – the not so typical questions are the one’s I’m interested in because they are what make you who you really are. I don’t want to be crossed off someone’s list because of some filter question. Maybe if you were to get to know the awesomeness that I possess, some of those other things wouldn’t be such a big deal anymore. Its like we enter the date asking questions that will quite possibly turn us off for the entire date. Why do that to yourself?!

      Liked by 1 person

      • Very true…. I think the bigger issue or straight forward thing is in three categories…. (1) What are you looking for, and give me a scenarios of this? qualities, aspiration, possible day to day week to week motions (2) What are your honest to god deal breakers? pet peeves, dislikes, no fly zones… (3) What are your top qualities do you see that will work for you in a relationship or potential partner, are you willing to invest time in developing together? I think is there are honest answers in these straight forward questions, it will cut out all the fluff that may wait your times.

        Liked by 1 person

  8. YOU. ARE. AMAZING. Lolol, I love it! :D


  9. Interesting and hilarious LOL…. my takeaway is that you think too much! hahaha.. but I already knew that… I don’t have a problem with any of these questions! and I’m one of those pricks form number 2 LOL! Good write though :)

    Liked by 1 person

    • lol! You know me well. Challenge yourself to remove number 2 from your dates just ONCE – for ME. See where the date goes without it. I bet you’ll come back with roses and a go-fund me account for promoting this article. haha! Just kidding. Thanks for the love, as always :) PS – I finally deactivated FB for an extended period. It feels amaze-balls!

      Liked by 1 person

  10. Great piece! I have been off the “market” a long time, and have forgotten what it was like to be single. I sorta feel bad for people who are single and looking for a committed relationship – because the “game” has changed in many respects.

    While some people might advise against this, I would personally like to know a little bit (just a little bit) about her political orientation. I would quickly ask a question about a hot-topic current event like the election: so, how do you feel about Trump getting elected? And I would not expect a long-winded answer, and I would try to keep this conversation kinda lighthearted. But if she is a Trump supporter or sympathizer, she has to go. No debating. Doesn’t matter how cute she is …it will never, ever work out. That is something to screen out on the first date – especially because I am a very “political” person.

    Liked by 1 person

    • lololol! WHY am I not surprised to hear this from you?! Now that I’ve gotten to know you a bit better through your posts, I am totally in agreement with you. This question is a MUST! You should introduce yourself when you meet a woman as “Darryl, non-Trump supporter.” Just get it out of the way before a conversation ensues hahaha. Question for you – what does a woman’s political orientation tell you about the future you could(n’t) have with her? FYI – you should write about this topic…it would be SO good!

      Liked by 1 person

      • My friend! How are you?! I hope you are having a good holiday season!

        You know what … that is a great question and prompt to respond to! I am going to get on that and link to this piece of yours. Thanks for the idea 😀 I look forward to your feedback!!!


  11. So, I cringe when I hear the question: Last relationship jazz? Ummm, obviously it’s over an I would never tell you everything because you’re still a stranger. And, the kids questions simply flies out of my mouth every time. I think it’s a way of preparing the conversation if it gets to awkward refer back to the kid or work. Lol. I’d like to think I’m a god conversationalist.. as long as you can hang. Add a little sarcasm, wit, humor. . .and you’ve got me ;’)

    Liked by 1 person

    • sarcasm + humor = the man of my dreams lol. I’m with you sis! That’s actually a pretty good idea – to refer back to kid or work if the conversation goes left. EVERY parent seems to love talking about their kid so I’m sure they would love to know you’re interested. And yes, the relationship question just…. :| …. enough said lol

      Liked by 2 people

  12. Number 5 though.. You are one hell of a thinker, also seems you want to know almost all that’s in one’s head before you start a convo.. Don’t stop writing! Come too think of it Nosy Josie, you already have a fine career in writing, with this stuffs you have in your archive. #JustSaying ;-D
    Do have a great weekend and a great new year ahead..

    Liked by 1 person

    • lol! I would say that’s a pretty accurate analysis of me. I’ve been told for YEARS that I’m an over-thinker. I just can’t help where this little mind of mine goes. It just travels all over the place lol. Thank you so much for the kind words and encouragement. I’ve fallen off a bit but like eve writer’s New Years resolution … I plan to do better in 2017. So cliche! lol :D. Happy New Year to you!

      Liked by 1 person

  13. haha Omg I so LOVEEEEEEEEE this post! “Truth be Told”

    Liked by 1 person

  14. I thought I was your online work husband LOL!

    Liked by 1 person

  15. lol you’re so awesome. Thank you for the reblog! I may be giving you that call myself hahahaha!


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