Talking to someone new or even someone familiar can be made much more exciting with the right questions.
Rather than sticking to the usual small talk, why not sprinkle in some fun and unexpected questions? It’s a great way to learn more about each other and share a few laughs along the way.
I’ve compiled some of the most entertaining and thought-provoking questions you can ask. Each one is designed to make conversations more engaging and enjoyable. Curious to know what these questions are? Let’s take a peek!
Table of Contents
Conversation Starters
- What’s the most interesting thing you’ve read lately?
- If you could travel anywhere in the world, where would you go?
- What’s your favorite movie of all time?
- If you could have dinner with any celebrity, who would it be?
- What’s the best advice you’ve ever received?
- If you could learn any skill instantly, what would it be?
- What’s your go-to karaoke song?
- Do you have any hidden talents?
- What’s the funniest thing you’ve ever witnessed?
- What’s the weirdest food you’ve ever tried?
- If you could play any instrument, which one would you choose?
- What’s your favorite way to relax?
- If you were an animal, what would you be?
- What’s the craziest thing on your bucket list?
- If you could invent something, what would it be?
- What’s the most interesting place you’ve visited?
- What’s your favorite TV show right now?
- If you could live in any era, which one would you pick?
- What’s the best gift you’ve ever received?
- If you could have a superpower, what would it be?
Dating Advice
- What’s the most adventurous thing you’ve ever done?
- What’s your idea of a perfect date?
- If you could write a book, what would it be about?
- What’s your favorite childhood memory?
- What do you look for in a partner?
- If you could relive one day of your life, which would it be?
- What’s the silliest thing you’ve ever done in the name of love?
- What’s your favorite romantic movie?
- If you could plan a dream vacation, what would it be like?
- What’s your favorite thing to do on a lazy Sunday?
- What hobby do you enjoy that most people wouldn’t guess?
- What’s the best meal you’ve ever had?
- If you could change one thing about yourself, what would it be?
- What’s the most embarrassing thing that’s ever happened to you on a date?
- What’s your most cherished possession?
- If you could only eat one type of cuisine for the rest of your life, what would it be?
- What’s the most thoughtful gift you’ve ever given someone?
- What’s your favorite way to spend time outdoors?
- If you could switch lives with anyone for a day, who would it be?
- What’s your favorite memory from a past relationship?
Relationship Building
- What’s your favorite way to spend quality time with friends?
- What’s the best road trip you’ve ever been on?
- If you could host a dinner party with any three people, who would you invite?
- What’s the funniest prank you’ve ever pulled?
- What’s your favorite holiday tradition?
- What’s a goal you’ve set for yourself this year?
- If you could take up a new hobby together, what would it be?
- What’s a topic you could talk about for hours?
- What’s the most interesting thing you’ve recently learned?
- What’s your favorite memory from school?
- How do you show appreciation for the people in your life?
- What’s the best concert you’ve ever been to?
- If you could go on a spontaneous trip right now, where would you go?
- What’s your favorite board game to play with friends?
- What’s the weirdest thing you’ve ever done together with a friend?
- If you could create a new holiday, what would it celebrate?
- What’s your favorite movie to watch with friends?
- What’s the best compliment you’ve ever received?
- If you could be any character from a book or movie, who would you be?
- What’s the funniest inside joke you have with someone?
Social Skills
- What’s the best way to start a conversation with a stranger?
- What’s your go-to funny story to tell in social settings?
- If you could master one social skill overnight, what would it be?
- What’s the most interesting fact you know?
- What’s your favorite way to meet new people?
- What’s the funniest thing that’s ever happened to you at a party?
- What’s your favorite topic to talk about at social gatherings?
- If you could attend any event in the world, what would it be?
- What’s your best icebreaker at a party?
- What’s the most unusual job you’ve ever had?
- What’s your favorite game to play at parties?
- What’s a surefire way to make someone laugh?
- What’s your favorite memory from the last party you attended?
- If you could throw the ultimate themed party, what would the theme be?
- What’s the best compliment you’ve ever given someone?
- What’s your secret to making small talk interesting?
- What’s the most unique conversation you’ve ever had?
- What’s your favorite way to break the ice with someone new?
- If you could invite anyone to dinner, living or dead, who would you choose?
- What’s the most spontaneous thing you’ve ever done in a social setting?
Personal Growth
- What’s the biggest lesson you’ve learned this year?
- What’s the bravest thing you’ve ever done?
- What’s your favorite way to challenge yourself?
- What’s a new skill you’ve recently learned?
- What’s your proudest accomplishment?
- What’s your favorite book on personal development?
- What’s a goal you’re currently working towards?
- What’s the best piece of advice you could give someone?
- What’s a fear you’ve overcome?
- What’s the best decision you’ve ever made?
- What’s your favorite way to practice self-care?
- What’s one thing you’re grateful for today?
- If you could give your younger self one piece of advice, what would it be?
- What’s the most inspiring quote you’ve ever heard?
- What’s your favorite way to stay motivated?
- What’s the biggest risk you’ve ever taken?
- What’s your favorite success story?
- What’s a habit you’re working on developing?
- What’s the most important lesson you’ve learned from a failure?
- What’s your favorite way to celebrate your achievements?
