Dolly Doctor

Love A List But Lost For Words? 50 Questions To Ask Your Date

Convos for days.
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Every guy or gal knows that dating can be a *daunting* time. 

From sussing out what to do, what to wear and don’t even get us started on texting etiquette (just don’t be a pen pal, pls), we barely have time to even think about what the actual date might entail. 

WATCH: Felix Mallard stars in Ginny And Georgia

If you, like us, love a good list to sooth the brain and bring a sense of calmness to your surroundings, then you might find the below useful.

We enlisted the help of Dolly Doctor to give us a couple of cues and tips as to what to ask a guy or girl – from the crushing stage right through to the full-blown BF/GF stage, because it’s important to be on the same page.

Here’s what Dolly Doctor has to say:

Sussing your crush out can be tricky business. (Getty)

Status: You’ve just started crushing

Ask these if: It’s essential to suss out if you have the same sense of humour.

  1. What YouTube / TikTok video ALWAYS makes you laugh?
  2. What’s the lamest joke you’ve ever heard?
  3. What award would you get at graduation? (Most likely to succeed, class clown etc)
  4. What’s the weirdest/funniest/best text message you’ve ever received?
  5. What’s the worst hairstyle/haircut you’ve ever had to live with?

Ask these if: You totally need to know what you’ll be watching/listening to/eating on your future dates together, right?

  1. What posters do you have up in your room?
  2. Do you have a crush on a TV character?
  3. How would you spend your ideal Saturday?
  4. What’s the most-played song on your phone?
  5. Would you prefer a day at the beach or movie marathon?
  6. If you could only eat one food for the rest of your life, what would you pick?

Ask these if: Basic getting-to-know you stuff will help you decide if you want this crush to develop into more.

  1. If tomorrow was a casual clothes at school, what would you wear?
  2. Who’s your best pal?
  3. Do you think you could give up technology for a week?
  4. Are you a cat or a dog person? (Or if they’re neither – why?)
  5. What’s your pet peeve?
  6. What age are you most looking forward to being and why?
  7. Do you have any nicknames? What do they mean?
  8. Have you ever broken any bones? If so, how?

What’s the verdict?

Suss whether their responses make you smile. If you liked 10 or more of their answers, you’ve landed yourself a winning crush. Spend more time with this person, confess your feelings and see where things go!

Liked less than 10? This just might not be the crush for you. Instead of limiting your every thought to this one person, start exploring some other crush potentials too.

The questions can vary depending on your situation. (Getty)

Status: You’ve made things official

Ask these if: If you value the same bigger-picture stuff, your new love is off to a pretty good start. 

  1. Would you rather be twice as smart or twice as happy?
  2. If you asked your principal for a reference, how would you want them to describe you?
  3. What did you want to be growing up?
  4. What’s your favourite school subject?
  5. Are you planning on studying after Year 12?
  6. What’s at the top of your post-school bucket list?
  7. What’s the first thing you’d save in a fire?

Ask these if: You want to test their honesty (or dishonesty) policy.

  1. What’s your worst habit?
  2. What’s the biggest fib you’ve ever told?
  3. What was the last phone call you avoided and why?
  4. Do you find it hard/weird apologising?
  5. Do you ever eat food that’s been dropped on the floor?
  6. What’s the most embarrassing thing that’s ever happened to you?

Ask these if: You want an insight into their home life, which might explain good/bad behaviours.

  1. What’s one thing your mum always tells you?
  2. What’s the last thing you argued with your parents about?
  3. What’s something your parents would be surprised to find out about you?

What’s the verdict?

If you liked 11 or more of their answers, this boyf/ or girlfriend has proven themselves to be a keeper. Our prediction? Your relationship can only grow from here. Liked less than 11? There are obviously reasons you guys matched up in the first place, but do you need to take another look and see if those reasons still exist?

Ginny & Georgia taught us a couple of things about the complexities of dating… (Netflix)

Status: You’ve been BF/GF forevs

Ask these if: Sometimes you just need to make sure you’re still on the same page.

  1. Would you rather unlimited money or love?
  2. What’s your on your “dealbreaker” list?
  3. What traits do you find most attractive in girls?

Ask these if: You want to test your D&M abilities to check that you can still make deep connections.

  1. What’s the last thing you daydreamed about?
  2. How do you feel when your best mate gets a new BF/GF and spends less time with you?
  3. What would you do if you didn’t like your mate’s new GF/BF?
  4. What’s the most important thing in a friendship for you?
  5. What’s the best compliment you’ve ever received?
  6. When were you the most nervous you’ve ever been?
  7. What’s your favourite thing about yourself?
  8. What’s one thing you’ll never do again?
  9. What’s the worst fight you’ve had with a mate?

Ask these if: You want to want to find out about their future plans (and ahem, if you’re in them).

  1. Are you excited to leave school?
  2. Where would you live if you could live anywhere in the world?
  3. Do you think our relationship could survive after school?

What’s the verdict?

If you liked 9 or more of their answers, this loved-up sitch hasn’t hit Snoozetown, that’s for sure. Keep the open convos going to make sure it never does.

Liked less than 9? Maybe it’s time to either shake up (think new hangtime ideas, new insights) or break up (think new dreams, new paths).

Have a question for Dolly Doctor? Drop us an email –

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