I used ChatGPT to ask better questions during conversations and people actually noticed

A man talking to a woman councillor in therapy about his sleep problems
(Image credit: Getty Images)

I’m kind of weird in the best way — I can go hours without talking to anyone, but once I’m around people, I make up for lost time.

The art of conversation has and always will be fascinating to me because I enjoy participating in chats that evolve from something minor to a major dialogue, whether it be over video games, politics, personal victories/losses and more. As a working journalist who interviews varied personalities and just an everyday guy who likes to talk to an equal number of familiar folks and strangers, I try to avoid asking the sort of questions that elicit “filler” responses.

I conducted another experiment with ChatGPT in the area of being a better communicator and conversationalist. This time around, I asked it to present me with better questions to ask during everyday discussions that refrain from being generic and actually produce deep responses from whoever I’m chatting with.

Article continues below

Abandoning 'filler' questions for good

People celebrating

(Image credit: Shutterstock)

Before ChatGPT assisted me in finding more thoughtful questions to add to my vocal repertoire, I took note of the hom-hum questions I asked on the regular.

Common questions like “how was your day?” and “what do you do for fun?” left my mouth far too often. So I used this prompt with the chatbot to get me going in the right direction: “Give me better versions of everyday questions that make people open up more naturally without sounding intense or fake.”

ChatGPT went on to present me with a list of alternatives for the most generic questions I (and I’m sure plenty of other people) use more than think:

  • Instead of “How was your day?,” try: “What was the best part of your day so far?,” “Did anything unexpectedly good happen today?,” “What took up most of your energy today?” and “What’s one thing you’re glad is over today?”
  • Instead of: “How are you?,” try: “How’s your week treating you?,” “What’s your mood been like today?,” “You surviving this week?” and “What’s been going good for you lately?”
  • Instead of “What do you do for fun?,” try: “What’s something you could talk about for way too long?,” “What’s your current obsession?,” “What do you do when you want to disappear for a few hours?” and “What’s something you always make time for?”
  • Instead of “Where are you from?,” try: “What kind of place did you grow up in?,” “What’s something about your hometown that people wouldn’t expect?” and “Do you still feel connected to where you grew up?”
  • Instead of “How’s work?,” try: “What’s been the most annoying part of work lately?,” “Has work been more chaotic or more boring recently?” and “What’s something at work you wish people understood about you better?”
  • Instead of “Seen any good movies lately?,” try: “What’s the last thing you watched that you actually loved?,” “What’s a movie/show you still think about afterward?” and “What’s something you watched that surprised you at how good it was?”
  • Instead of “What are your plans this weekend?,” try: “What would your ideal weekend look like right now?,” “Anything you’re genuinely looking forward to?” and “What’s the most likely way you’ll spend your Saturday?”
  • Instead of “What music do you like?,” try: “What artist have you had on repeat lately?,” “What song perfectly matches your current mood?,” “What’s a song you never skip?” and “What kind of music do you put on when nobody else is around?”

Putting these questions to work elicited some of the most insightful, funny and shockingly emotional responses from my best friends and parents.

Learning about my favorite people’s top movie picks, hearing humorous stories about their hometown and getting the lowdown on how their jobs have been stressing them out were the sort of intriguing topics that came up after I asked the right questions from the assortment of inquiries ChatGPT gave me.

Pulling out specific questions for a first date

a person sitting chatting at a christmas dinner table

(Image credit: Morsa Images)

Besides getting a bunch of questions that make for great chats with friends and family, I also took note of a slew of other icebreaker questions that I figured would lead to great convos during a first date.

Feel free to let me know if you think these inquiries are right for that sort of social situation:

  • “What’s something you used to hate but now totally get?”
  • “What’s something people assume about you that’s completely wrong?”
  • “What’s something small that’s made your life noticeably better lately?”
  • “What’s your most shocking hot take?”

The takeaway

Striking up a quick convo with the people I personally know, my coworkers and unknowns that could turn into new friends is a personal hobby of mine. I love to chill by myself more often than not, but I’m always down to talk for hours on end about anything and everything.

Taking note of people’s surprised reactions after being presented with the new questions I brought to every chat was fascinating to witness. And it was equally cool to see them take notice of how much more meaningful my questions for them came off compared to our previous meetings.

Once again, ChatGPT has exposed me to usable methods that make every conversation that much more interesting.


Click to follow Tom's Guide on Google News

Follow Tom's Guide on Google News and add us as a preferred source to get our up-to-date news, analysis, and reviews in your feeds. Subscribe to Tom's Guide on YouTube and follow us on TikTok.


More from Tom’s Guide

Category
Storage Size
Colour
Minimum Price
Any Minimum Price
Maximum Price
Any Maximum Price
Showing 10 of 18 deals
Filters
Arrow
Show more
Elton Jones
AI Writer

Elton Jones covers AI for Tom’s Guide, and tests all the latest models, from ChatGPT to Gemini to Claude to see which tools perform best — and how they can improve everyday productivity.

He is also an experienced tech writer who has covered video games, mobile devices, headsets, and now artificial intelligence for over a decade. Since 2011, his work has appeared in publications including The Christian Post, Complex, TechRadar, Heavy, and ONE37pm, with a focus on clear, practical analysis.

Today, Elton focuses on making AI more accessible by breaking down complex topics into useful, easy-to-understand insights for a wide range of readers.

You must confirm your public display name before commenting

Please logout and then login again, you will then be prompted to enter your display name.