Growth & Inspiration Style

50 Meaningful Conversation Starters

There is one question that’s always on the tip of our tongues in countless places. At the bar, the networker,  and the casual blind date, the words slip out before we have a chance to retract and think of anything more compelling. Four bland words punctuated by a question to feign interest: “What do you do?” In a world where we are so driven by what others do for a living, I think there is an opportunity to use our conversation starters to discover who people are deep down. 

Our job title doesn’t define us and doesn’t truly explain to someone who we are as a person. Carol, the administrative assistant, isn’t the sum of her organization skills, file folders full of invoices, and her ability to sound chipper on the phone. Maybe Carol loves making artwork on the side, has been to 20 countries, and plays the violin! To discover who someone is, we should stop putting them in the box of what they are doing in this instant. Don’t get me wrong, a job you love can be your defining strength but it doesn’t paint the whole picture and tell the story of you. Talking about your work can create a common bond, but don’t let yourself think it’s the only bond you can share with someone. 

At Yellow Conference two years ago, I had the chance to hear SoulPancake CEO, Shabnam Mogharabi, speak about human connection. At the beginning of her speech, we were asked to start a conversation with the person next to us using questions from an unconventional cue card of conversation starters. In turn, the stranger next to me got to know things about me I never thought to mention. Ever since, I’ve been battling with myself to avoid the common, “What do you do for a living?” 

My 50 Meaningful Conversation Starters

50 Meaningful Conversations Starters Cup of Charisma Lifestyle Blog

Without further ado, here are 50 conversation starters I’ve picked up over the years. 

  1. What excites you in life? 
  2. If you had one hour left to live, how would you spend it? 
  3. What matters to you most? 
  4. What brings you joy? 
  5. What is the best advice you ever received? 
  6. What makes you laugh out loud?
  7. How do you know when you’ve made the right decision? 
  8. What’s the purpose of art? 
  9. What’s one lie you’re glad you told? 
  10. What’s your favorite book and why? 
  11. If you had to choose your last meal, what would it be? 
  12. What was the highlight of your day today? 
  13. What was your dream job when you were a kid? 
  14. What’s the best place you’ve traveled to? 
  15. What’s a mistake you’re glad you made? 
  16. What recharges you on a bad day? 
  17. What is your favorite hobby? 
  18. Who is your biggest role model? 
  19. If you could have dinner with anyone in this world, who would it be? 
  20. What would you go back to tell your childhood self? 
  21. If you could go back into any period in time, what would it be? 
  22. What do you think of when you think of the word home? 
  23. Cat or dog person? Why? (Bonus points if they are both!)
  24. How did you meet your best friend? 
  25. What’s the most beautiful place you’ve ever visited? 
  26. What’s one thing on your bucket list? 
  27. What’s your favorite band? 
  28. What was your best live concert experience? 
  29. What was the last book you read? 
  30. What is the first thing you notice about people? 
  31. What inspires you most? 
  32. If you could write a book, what would it be about? 
  33. When was the last time you did something for the first time? 
  34. What’s your most important personal truth to live by? 
  35. Are you a night owl or an early riser? 
  36. What are you most afraid of? 
  37. What’s a personal goal of yours? 
  38. Are you a planner or do you prefer to live life spontaneously? 
  39. If you could travel in time, what period would you go to? 
  40. What’s your fondest memory of a holiday? 
  41. What do you do to unwind? 
  42. What’s your favorite or least favorite exercise? 
  43. Why did you come to [insert wherever you are] today? 
  44. What’s the best gift you’ve ever received? 
  45. What’s the best gift you’ve ever given? 
  46. If you were in charge of the playlist, what would you play next? 
  47. What’s your favorite TV show? 
  48. Do you prefer the mountains or the beach? 
  49. What can you do to make the world a better place? 
  50. What things in life should always remain a mystery? 

I challenge you to use one of these conversation starters to create a meaningful connection with someone past their desk job. 

Outfit Details

Now let’s talk about the outfit featured on this post because I can’t contain my excitement when wearing this dress. The Faith in Elegance Dress at Chicwish immediately caught my attention when I was browsing online. It was my first time ordering from the site, and I was pleasantly surprised when this little number came in the mail. Everyone could benefit from the perfect Little White Dress. My LWD has gotten me around Houston, making me look cute and polished at everything from brunch to brand dinners. I’ve received so many compliments!

There is a nude lining under the dress, allowing for a fun peekaboo-style design. The flair sleeves and collar make the look feel preppy and feminine. I paired this dress with a pair of my favorite blush heels (they are sold out, but I’ve linked a similar pair here), gorgeous Mignonne Gavigan statement earrings, and my Gucci bag.

This dress is selling out fast, so be sure to snag your size online for only $72.90 on sale. The dress also comes in a red color that I love. Chicwish has a ton of great dresses for special events and everyday wear, so I can’t wait to share more looks with you.

What’s your favorite conversation starter to use? Let me know in the comments!


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