Random Questions to ask your Significant other when you’re extremely Bored

As great as my relationship is with my husband, and as much as he is my bff in the whole wide world, there's sometimes where there's just not much to talk about. Either that or we're really bored and too dull to think of meaningful conversation. In those moments we often play the game of 20 questions (that just being the name of the game, not really the number of questions we ask each other).

As great as my relationship is with my husband, and as much as he is my bff in the whole wide world, there’s sometimes where there’s just not much to talk about. Either that or we’re really bored and too dull to think of meaningful conversation. In those moments we often play the game of 20 questions (that just being the name of the game, not really the number of questions we ask each other). I’m a pro of thinking up great random questions to ask Josh. He… well… he thinks too much and tries to come up with the perfect question which takes about 20 minutes to do and so for every 1 question he asks me, I’ve already blurted about about 50 quality random questions. Some will make you laugh, some will make you think. Either way, if you test these out on your significant other, you’re be sure to learn something new 🙂 Let me know that you think and post your own random questions in the comments!

    • If you could change your career to any career you wanted, what would you do instead?
    • If you could live anywhere in the world, where would it be?
    • If you were to spend your life serving one kind of people group, who would they be?
      1. (could be a race, the elderly, children, special needs, military families, etc.).
    • Who is your favorite superhero and why?
    • Do you like breakfast or dinner better?
    • Would you rather spend a weekend out and exploring and trying new things, or settled in at home reading a book (and/or binging on netflix)?
    • What is your favorite season of the year and why?
    • If I were going to wear lipstick, what would you choose between bright pink or maroon?
    • Would you rather watch a funny movie or an action packed adventure or war movie?
    • Cats or dogs?
    • Which sounds more like your ideal date:
      1. Dinner and a movie?
      2. Fishing?
      3. Coffee and strolling around town?
      4. Playing a board game together?
      5. Laser tag with friends?
    • What’s your favorite book you’ve ever read and why?
    • Would you rather be able to speak 10 different languages or be psychic?
    • Coffee, tea, or hot chocolate?
    • What’s the most romantic thing we could do this weekend?
  • What’s the most adventurous thing we could do this weekend?
  • If you could be a model for any type of product, what would it be?
    1. (i.e. a foot model, makeup model, rugged sportswear model, etc.)
  • If you were stranded on an island for a month, what are 3 things you’d bring with you?
  • If you could take an elective college course or certificate program, what would it be in?
  • If you had to choose an actor/actress to play the role of you in a movie about your life, who would you choose?

Got some to add? Let me know! I’ll be sure to use them during our next road trip!

LTSW Signature


  • comment
  • Facebook
  • Twitter
  • Pinterest
  • Google+
  • Stumble
  • Email
  • Follow @Chelsealeighdamon on Instagram!

    Leave a Reply

    Your email address will not be published. Required fields are marked *



    If this were a game show I would have just won. This is fun to do. We have don it so often that hubby and I have moved on to stranger topics.

    You get one superpower. What and why?
    If your past life was a famous person in history? who and why?
    If the world as we know it ended, what wouldn’t you do to survive?
    And of course the one I get tired of but hubby likes to ask.
    If we won the lottery…..?

    Great post!!

    Becky @ Disney in your Day

    This is great… I’m totally saving it for a boring car ride! And my husband sounds a lot like Josh. He would spend wayyy too much time trying to come up with questions!


    That’s fun. Like a quiz. Get to learn more about each other at the same time.


    These are so great, I can’t wait for my boyfriend to get home from work so I can pester him with these!


    Love this! And it’s nice to know it’s ok to not have great ideas on meaningful conversation at times!


    These are some great questions. I’ll have to keep these in mind for the day when I actually get a boyfriend lol 🙂


    Great idea! I am going to try it 😉

    Mash | http://www.sarmash.com


    This is fun! We have a book called “The Little Book of Stupid Questions” and it comes in handy for road trips too! 😉


    Love this game— gonna use your questions the next time! Thanks for sharing..
    — DT | Here I Scribble

    Alexandra @ My Urban Family

    These are so fun! Just last night my husband and I were playing “this or that” where you ask a this or that and they have to answer right away without thinking. Mostly silly questions, but it was a fun 15 min before bed.

    Karin Rambo

    What a great list! I like what Becky said about saving it for a boring car ride.


    Love this idea. So cute 🙂 I like the last question lol. It’s gonna be interesting to see what my husband says to these. Thanks for sharing 🙂

    Aishwarya S

    This is such a fun activity. Definitely going to try this out with friends when we get bored.

    Shann Eva

    Love this! We are planning a road trip for this Spring, so you know I will be bringing these out. I’ll have to think of some for the kids too. They’ll love it.


    Love these! I can’t wait to annoy my husband tonight with these questions! Haha!


    great post! sadly, i don’t think i know the answers to most of these questions and I’ve been married for 3 years :/. Ill have to spend some time with hubby getting to know each other again! thanks for the idea!


    I love this! My husband is in the military which made it a little challenging when it came to him dating and talking to women. Decisions have to be made a bit more quickly than in a normal civilian relationship so when he and I first started talking, we asked A LOT of questions. We knew pretty early on that we really liked each other and wanted to turn it into a relationship so before we did, we asked EVERY question under the sun. We wanted to make sure we were actually compatible and wanted the same things out of life before decided to enter into a relationship. Clearly, it worked because we actually got married two months later and have now been married for 2 years 🙂 I loved getting to know him and still enjoy asking these random questions whenever they pop into my mind.

    Lisa Sharp

    My husband and I love to do this! These are great questions, thanks.


    What a fun post! As of right now I’m flying solo but I think it’s fun to ask crazy questions and what not when I do have a S.O.

    Rachel G

    My husband and I are known for asking each other (and sometimes new people that we just met), extremely random questions that pop into our minds. You’ve got some really funny and thoughtful ones here, I love it!

    Liz Jo

    yes love these questions. I’m the queen of asking the craziest questions to Kyle.

    liz @ sundays with sophie

    Rosalyn O.

    These are some very thoughtful questions!! I don’t have a partner at this point in my life but I will Pin for future reference!! Thanks!


    I play a game like this recently. It was so much fun hearing the answer to some of the questions.


    I’m definitely going to pass these along to my newlywed friends! Haha Some of these would be good blog post ideas too.


    totally pinning this for a date night!

    Allison Jones

    Great questions! My husband and I have a long travel day coming up so we’ll be utilizing these as we sit in the airport and on the plane.



    Love stuff like this!

    Emilie Burke (@burkedoes)

    Definitely saving this for date night!


    I’ll definitely be asking my boyfriend some of these over lunch. This is such a cool idea. Thanks for sharing!

    Heather with WELLFITandFED

    So totally obnoxious that we already know answers to almost every one of those already. We love playing those games. Such great conversation starters though right?


    Loveee this idea. I’ll be asking my husband some in about 5 min. Our baby will be asleep and then we definitely will be bored. Lol

    Katie @thebrooksielife

    These are great! How fun! We spend a lot of nights in, which we enjoy, though this would be fun to do to change things up a little.


    I bet you have a blast when you ask each other these questions!!


    Keeping this for a rainy day! Awesome post!
    May from http://www.mayliving.com

    Brianne Grogan

    I’m so excited! My hubby and I have a date night this weekend, and I’m TOTALLY going to print out these questions and bring ’em. After almost 11 years of marriage, it’s good to shake things up now and again and random questions are a great way to do it! Thanks! Loving your site!


    I’m in a long distance relationship and sometimes we run out of topics to talk about since we basically text all day. These are great! I’ll definitely be asking him some of these questions. Thanks!


    and you get married without asking those questions and more before ??? seriously ?? kidding 🙂 …..i am master mind of questioning…my darling says that in previous life i was spanish inquisitor or something 😉 I know all the answers 😉

    Raleigh Greer

    Woah! I’m really enjoying the template/theme of this blog.
    It’s simple, yet effective. A lot of times it’s tough to get that “perfect balance”
    between usability and appearance. I must say that you’ve done a
    fantastic job with this. Additionally, the blog loads extremely
    fast for me on Firefox. Excellent Blog!


    Great list of Q’s… After 40+ years of marriage, my husband would still always cringed if I wanted to talk about ‘feelings’, but he would leap at the chance to answer, “If we won the lottery…..” then wax on for miles about his plans. Perfect.


    This is a cute and fun read thanks for sharing from one modern day girlfriend to the next!