The Sunday Edition is Tuesday’s little sister—off-the-cuff updates I’d bring up over a coffee catch-up with a friend.
In my twenties, I worked at a coffee shop. One afternoon, my boss gave me a tip: “When people are coming in, don’t ask ‘How are you?’” she said, explaining: “It can be a really difficult question to answer. I want people to show up here and feel at ease.”
At the time, I got the sentiment, but I couldn’t fully appreciate why someone might not want to hear, let alone answer, “How are you?”
Flash forward a decade. I sent a joking-but-not voice note venting about “How are you?” Each time that I hear it, my mind goes to the email inbox that hasn’t been addressed. Or the upcoming kids sportsschedule that is going to run my life. Or a recent headline out of the White House.
I’ve always loved seeing other people, from weddings, reunions, and birthday parties to yes, networking events. But I need some alternative questions to ask and answer. Here are 30 great questions I rounded up for every occasion.
For milestone events, like weddings, memorials, reunions, graduations, and parties, ask questions that let people tell stories instead of giving updates:
What’s your favorite memory of [the person or people being celebrated]?
Do you remember how you first met [the person or people being celebrated?]
What’s changed the most since we last saw each other?
Is there a tradition your family has for [this type of event] that you particularly love?
What’s been the highlight of your year so far?
If you could give one piece of advice to [the couple/the family/our younger selves], what would it be?
For kid-centric events, including baby showers, kids’ parties, and school events, focus on life transitions:
What’s the best parenting hack you’ve discovered lately?
What’s the best advice you received when you were [expecting/entering X life phase/etc.]?
Do you have any traditions from your own childhood you’ve held onto [as an adult, with your family now]?
How has your social life changed since [having children/kids started school]? Any tips for balancing everything?
What’s something your kid has taught you recently that surprised you?
What’s the funniest thing your kid has said or done lately?
What’s been a top memory so far as a [parent/with your kids this year]?
For community events, including block parties, volunteer groups, exercise classes, and housewarmings, we focus on our connection to place and shared experience:
What’s your favorite local spot in this neighborhood?
What’s your favorite local tradition or event in [neighborhood, town]?
I’m looking for a good [local service, type of restaurant, activity] — do you have any recommendations?
Do you know the story behind [interesting local landmark or tradition]?
Have you tried that new [restaurant/shop/facility] that opened nearby?
What are your favorite [day, weekend] trips from [town]?
For professional events, such as conferences, networking events, offsites, and work dinners, get past job titles to what people actually care about in their work:
What’s been your favorite project to work on this year?
What brought you to this industry originally? Did you think you’d go into this field?
I’m curious, what does a typical day look like for you?
How do you describe what you do to your friends and family?
What’s something that’s changed in your field that most people don’t think or know about?
What’s a tool or resource you couldn’t live without?
Have you read any good books or articles related to [field] lately?
What’s the most surprising thing you’ve learned since starting in [industry, role, field]?
If you weren’t in [field], what would your alternative career be?
At the end of the day, the questions we ask can open doors,or close them. Swapping out “How are you?” for something more thoughtful doesn’t just spark conversation; it signals that we really want to know the person in front of us, not just the surface-level update. I’m reminding myself that the best connections come from curiosity, not small talk. So maybe the next time we see each other, I’ll skip “How are you?” and ask something better instead. And who knows, you might just walk away with a story you didn’t know you needed.
The Second Act is an entirely reader-supported publication written and created by Danielle Wraith. Click here to subscribe or gift a friend a subscription here (if a friend sent you this —tell them thanks!). Anything you want covered? Questions? Reply with a comment below! You can also find me on Instagram. Please come say hi!