My 5 Favorite Non-Small Talk Questions for Building Deeper Connections

Because “How are you?” never really gets anywhere.

Small talk has long been a pet peeve. Perhaps this is due to my innate introversion or experiences interviewing people for writing projects — I like to get to the real stuff immediately.

But, of course, small talk has its place in various situations. The issue is when the trivial questions never give way to deeper truths, particularly when building stronger connections for friendship, romantic, or professional purposes.

Over the years, I’ve come up with five go-to segue questions — questions that feel appropriate after discussing the basics and warming up to the person a bit. They’ve always been well-received, and I’ve found that they “break the ice” and let me relax my shoulders a bit.

1. “How did you meet your spouse/partner?”

This one brings me the most passionate responses of all the non-small talk questions I whip out. People love talking about… love. Especially when it’s their own story. I’ve heard some of the most advantageous, almost fairy-tale-like encounters. From swoony meet-cutes to friends-to-lovers tales, hearing people recount their love stories is heartwarming.

Before asking this question, you want to know whether the person is in a relationship/marriage first (and pick up on whether they talk about it positively or at least neutrally).

2. “What inspired you to get into [X] profession/hobby?”

Another facet of life people enjoy talking about (whether it’s to complain about toxic working conditions or genuinely gush about the wonderful clients they collaborate with) is work. It makes sense, given how much time the average person spends on the clock.

If work hasn’t come up in the conversation yet — whether it’s just a topic you’re steering clear of, the person hasn’t said anything, or they’re unemployed/retired/on long-term leave/etc. — consider asking about hobbies. If they haven’t mentioned any, start with the classic, “What do you enjoy doing in your free time?” and go from there.

3. “What’s your dream travel destination? And why?”

This is always a favorite! Travel tends to light many people up — whether they’re avid globetrotters or dream of visiting a particular destination someday.

I also find this question helpful in gauging a person’s values and interests. Do they want to go on a month-long yoga retreat in Bali? Set sail on a luxury Mediterranean cruise? Volunteer with underserved communities in sub-Saharan Africa? Backpack through South America?

The point here isn’t to judge, but it’s always interesting to hear about the places people hope to see someday. And it often spawns an ongoing conversation about previous travel experiences, which is a fun way to connect in its own right.

4. “If you could go back in time and give your 20-/30-/40-year-old self advice, what would you say?”

This is a more profound question, so I only pull it out if the conversation moves towards more reflective territory. But when I do ask, it’s led to very profound answers.

For instance, a few years back, I spoke to a cousin I hardly knew. He started talking about being in his late 40s and all his career regrets. I asked him what he would tell his 30-year-old self, and he said, “Don’t stress so much about the small stuff. And take better care of your body!”

The wisdom of those older than us (or roughly the same age) is an important reminder of what matters in life. Using their insights, we can ask ourselves whether the way we live would make our future selves proud. If not, this is a perfect opportunity for change.

5. “What are your biggest sources of creative inspiration?”

I ran an interview series in my newsletter last year and received feedback from most interviewees that this was their favorite. If there’s one thing creatives — writers, artists, designers, and so on — love talking about, it’s creativity.

I’m always surprised by the answers, ranging from the interviewee’s children to nature to mountain goats. (When I asked one woman to elaborate on the latter, she mentioned their humility and underdog-like strength. I was sold.)

When we learn what fuels others’ creativity, we can find new sources of inspiration for ourselves.

It All Starts With the Questions You Ask…

Many of us are in a place where we’re seeking more profound, more intentional connections. (Especially in the digital era, where texting and DMs have become a stand-in for keeping in touch.)

We all want to be understood and feel like we belong. Asking people more thoughtful questions that allow them to open up a bit more makes them feel seen for who they are. And it can potentially lead to new connections or, at the very least, a refreshing conversation.

What are some of your go-to questions when getting to know someone more deeply?

Thanks so much for reading! If you enjoyed this story, check out more, just like it, through my Substack, The Tuesday Tapestry.