E327: 7 Questions to Ask Your Friends to Go Beyond Small Talk and Build Deeper Friendships in Midlife

When was the last time a conversation with a friend went deeper than kids, work and weekend plans?

In midlife, our friendships are shifting along with everything else: kids leaving home, aging parents, changing careers and our own health. Most of us want deeper connection, but we don't always have more time. The answer isn't more time together. It's better questions.

In this episode, Stephanie and Marnie share seven questions that take a friendship beyond small talk, some inspired by health journalist Liz Moody and a few of their own. Then they put every one to the test, answering them together, honestly and with plenty of laughs. A few are fun icebreakers. A couple go surprisingly deep. And one might change how you respond the next time a friend tells you she's struggling.

🎧 Think of this one as your conversation toolkit. Save it and come back to it before your next walk with a friend, coffee date, girls' weekend or family dinner. You'll want the questions handy, and you may be surprised what you learn about the people you know best, and about yourself. 

Join us on Substack and receive a free printable document with the seven questions we share in this episode.

In this episode, you'll hear:

• The quick-fire icebreaker that reveals a friend's hidden passion

• What a "dream scenario" answer says about what's missing in your life

• Why women need to celebrate the small wins

• The upside of midlife nobody talks about

• The question to ask before you give a friend advice

• Why vulnerability is the foundation of deep friendship

Time stamps:

00:00 The quick-fire icebreaker we started with

01:39 Where these questions came from

02:23 Why friendships change in midlife

05:17 Something you've always wanted to try

11:19 The dream-scenario question (and what it reveals)

14:31 Looking back on how far you've come

16:33 Why women need to celebrate small wins

19:46 Why we stop following the crowd in midlife

 21:15 Telling a friend what she brings to your life

24:21 The question to ask before giving advice

26:07 Why vulnerability builds deeper connection

27:40 How to try these questions this week

Ask us anything: Join our Substack to get the link to our monthly Ask Me Anything session, plus episode updates, wellness tips and personal reflections from Marnie and Stephanie. https://theartoflivingwell.substack.com/

Join the 14-Day Winter Vitality Reboot Start 2027 feeling clear, energized, and back in your body. We are guiding the Winter Vitality Reboot from Tuesday, January 5 to Monday, January 18th.  Early-bird pricing is $295 through December 11 ($325 after). Join us: https://l.bttr.to/vYa42

Do It Anytime Vitality Reboot: Ready to reset your energy, cravings and habits on your own schedule? Start our self-paced Vitality Reboot anytime. https://p.bttr.to/39XDmpQ

If this episode resonated, share it with the friend you want to ask these questions, and tell us which one you tried.

Connect with Us