30 lifestyle conversation starters for deeper connections

Table of Content

There are a million questions you could ask in a conversation.

Should you just bombard them with all the questions you can think of… or pull out a random list of 100 conversation starters you saw online?

Probably not…

That’s not how you build relationships, yo

In this article, I will share specific lifestyle conversation starters you can use to talk with anyone, whether you’re at a professional event or party.

What makes me uniquely qualified to write about this?

Over the last ten years — across three continents — I’ve started conversations with thousands of strangers. I’ve also interviewed well over 700 people for my projects (namely a street journalism project and a book).

Speaking about my experience talking with strangers at TEDx!

In other words, I’ve asked more questions to spark meaningful conversations than most people.

I can’t guarantee that my conversation starters will work every single time, but I’d like to think that I have a better gut sense of great vs. blah questions.

What are lifestyle conversation starters? Why use ’em?

Here’s how Cambridge Dictionary defines “lifestyle”:

“someone’s way of living; the things that a person or particular group of people usually do”

And that’s why lifestyle conversation starters are all-encompassing. They can be about:

What career you chose and why
How you spend your free time, whether it’s relationships or hobbies
Where you choose to stay
What you choose to buy/rent e.g. house, car, clothes

When and how to use these questions

No hard rules per se, but here are a few suggestions:

Ask questions about someone’s lifestyle after you’ve built some rapport with them. As these questions can go fairly deep, an acquaintance might feel uncomfortable about sharing their honest thoughts.
Use the most relevant questions for the social situation. For example, if you’re at a networking event, start with career-related lifestyle questions before getting personal.
Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.
Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation 🙂 I’ve been guilty of that.
Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.

Why is that important? Different people have different ways of saying things.

The more you can tailor the conversation starter to your tone of voice, personality etc., the easier (read: less awkward) you will find using it.

To make this more usable for you, I’ve tried introducing variations of the same question 🙂

Lifestyle conversation starters

Career-related

For more career conversation starters, check out my other article.

Small talk	Where do you currently work? // What’s your work environment like? Who do you work with? Do you prefer working in an office or working from home? Do you prefer working in a small or big team? What’s your typical workweek/day like?
Deeper questions	What’s your ideal work environment? // Where do you get the most work done? If you could work from anywhere in the world, where would it be? Who do you love/hate working with? // Who excites/drains you the most? What’s the favorite part of your workweek/day and why? What’s your ideal workweek/day and why?

Leisure-related

Small talk	What do you do after work? What do you do on your weekends? What’s your favorite thing to do on weekends? How do you prefer spending your free time? What do you do for fun? // What are your hobbies?
Deeper questions	What’s your ideal work-life balance? How do you balance work and fun? What’s your #1 guilty pleasure? // What’s your favorite way to “waste” time? Fill in the blanks: “___ by day, __ by night” // “___ on weekdays, __ on weekends” If you had all the time in the world, what would you like to experience and why?

Environment-related

Small talk

Where do you stay now?
Where were you staying before <location>?
What’s the commute to work like? // How far is home from work?
Where do you usually hang out?
What’s your favorite spot in your neighborhood/city? // What’s the most underrated spot in your neighborhood/city? (You can be more specific by replacing “spot” with restaurant, cafe, bar etc.)

Deeper questions

What do you appreciate the most about your neighborhood/city and why?
If you could wave a magic wand, what would you change about your neighborhood/city?
If you could stay/move to anywhere in the world, where would it be? Why? // What would be your dream city?
Where would you choose to retire? Why? // Where would you want to spend the rest of your life?
What gives you a sense of belonging and why? // What does home mean to you?