Fun Questions to Ask When Getting to Know Someone to Make It Less Awkward

Dear Mimi,

First dates, or even first meetings, can be less than graceful. With the holiday season upon us, it’s impossible to predict where we’ll meet someone: at holiday parties, on the plane, happening to pick the last item of something and fighting over it on Black Friday. The possibilities are endless. And heck, for us desi girls, meeting with a rishta for the first time can be (sorry, IS) all sorts of gawky and unpleasant. My advice? Make it into a game.

Okay before you jump to ‘my sister is inexcusably crazy’, hear me out. In the end, we all want someone who we can laugh, have fun, and be ourselves with. And what better litmus test? If the person you’re talking to finds it weird or thinks they’re above it, you know that’s not the person for you. But, if they go along with it, you learn a couple different positive things about them: 1) They aren’t afraid to have a little fun. 2) They can go with the flow. 3) They’re open to trying new things, even though they may be a bit uncomfortable. All good traits you should be looking for.


So here’s the game. Take turns asking questions about each other. Simple enough. And here’s the catch: Questions cannot be repeated. For example, if I ask ‘What’s your favorite color?’, the other person will answer, but they cannot ask me what my favorite color is. Capiche? This will add intrigue and a sense of depth in your conversation. If the person really wants to get to know you more, they will find a way to meet with you again so they can ask you the questions that they didn’t get to (because you asked them first, in case that was unclear).

Now, you have your basic questions like ‘What school do/did you go to?’ or ‘What do you do?’ or ‘How many siblings do you have?’ But here are some questions that are more interesting and will add a little more spice.

  • Favorite subject in school?
  • Favorite college class taken?
  • Worst college class taken?
  • Favorite book?
  • Worst book read?
  • Which house would the sorting hat put you in and why?
  • Favorite saying?
  • Quote you can’t stand?
  • If you could be best friends with any celebrity, who would it be?
  • Favorite superhero?
  • Most exciting thing on your bucketlist?
  • Which celebrity would play you in the movie of your life?
  • What would the title of your autobiography be?
  • Favorite dessert?
  • Most disliked food?
  • Best gift you’ve ever gotten?
  • Most exciting place you’ve gone?
  • Most overrated place you’ve visited?
  • Save or delete everything?
  • One place you’ve always wanted to visit?
  • Best $50 you’ve ever spent?
  • If you could receive a $1000 gift card to any store, which one would it be and why?
  • First memory?
  • Most used app on your phone?
  • Favorite TV shows?
  • If you could name yourself, what name would you choose?
  • Pet peeves?
  • Spirit animal?
  • Language you took in high school? Can you still speak it?
  • Favorite restaurant?
  • Most embarrassing moment?
  • Favorite scents?
  • Favorite noise?
  • If you could only eat one thing for the rest of your life, what would it be?
  • Ideal name for a pet?
  • Color you hate?
  • Summer or winter?
  • Best item in your closet?
  • One thing you can’t live without?
  • Biggest fear?
  • Toilet paper over or under?
  • Historical site you’ve always wanted to visit?
  • If you could change one event in history, what would it be?
  • What time period do you see yourself living in (besides today)?
  • What is one thing you’d like to see in your lifetime?
  • What would your ideal phone look like?
  • If you had a YouTube channel, what would it be about?

These are just some ideas. Feel free to add your own in conversation or in the comments below!

Hopefully things are now less awkward Mimi.




I don’t want a relationship that’s serious all the time. I want someone I can laugh, be silly with. Someone that not only gets my weird sense of humor, but thinks it’s hilarious too.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s