Questions of the Week


Throughout the year our Work/Life Weekly newsletter has featured a Question of the Week segment. Our goal was to provide a simple resource to help grow the relationships in your life. Also, by now it should be clear that I love a good conversation question.

I have compiled all the questions into one spot in case you need a go-to question for any moment this holiday season, whether you want to connect with someone else or make the silences less awkward. Spending time in solitude over winter break? Consider any of these questions for some journaling or introspection.


What made you proud today?

From On Our Sleeves Operation: Conversation


What is one thing you learned today?

From British Physician and Author, Dr. Rangan Chatterjee


What peculiar event contributed to us meeting?

From The Couples Quiz Book by Alicia Muñoz


What would your younger self from childhood think of you today?



What are some things that bring you joy?

What is your favorite sound, smell, and feeling?

What stories have you been told about yourself as a baby?

What about you led to your career choices?

– 4,000 Questions for Getting to Know Anyone and Everyone


What would constitute a “perfect day” for you?

If you moved away from the town you currently live in, what things would you miss and why?

Adapted from Arthur Aron's 36 Questions for Interpersonal Closeness


How is your day on a scale of 1-10? What can I do to move it up to a higher number?
From the book SuperBetter


What’s something you want to do in the next year that you’ve never done before?

- From Signalv.Noise: The 25 most popular icebreaker questions based on four years of data


What are you especially grateful for right now?

- From Christine Carter's post: 15 Questions to Ask Kids at Dinner


What were your favorite moments of 2022 and what do you want to learn in 2023?

- Adapted from facilitator, author and gathering expert, Priya Parker


Can you think of one act of kindness you would like to share tomorrow?

- From Greater Good's 29 Daily Conversations Starters for Kids


Who was your childhood hero, or heroes?

From Gottman's Eight Dates: Essential Conversations for a Lifetime of Love


What are some things that bring you feelings of calm?


What is one of your favorite places in the world and what about it is special to you?


Happy conversing!

For more questions for romantic relationships, check out my past blog post on questions for conversation and closeness.


About Author

Katie Seavey Pegoraro

Sr Associate Work Life Program Manager

Katie Seavey Pegoraro supports employees with issues of stress and balance, providing tools and resources to cope when life feels overwhelming. Katie is a contact for those who may be coping with issues of mental health, substance use, or grief and loss. A young professional herself, Katie is a unique support to employees who are navigating the many life transitions that occur in your 20's and 30's.

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