Deepening at home

how to go a little further with your people

Jan 22, 2026

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I was recently in a meeting that opened with a prompt that totally floored me. In a room with nearly 25 (mostly) strangers, we were discussing an upcoming retreat we’re all embarking upon in the coming weeks (excited to share more soon!) We were invited to pair off with someone we didn’t know and were instructed to ask:

why are you coming on this trip? [pause, listen to response]
why are you coming on this trip? [pause, listen to response]
why are you coming on this trip? [pause, listen to response]

No need to reply, no invitation to interact with the answer - just to ask the same question three times, give the person their space to answer and then, switch.1

As it was described, I thought… hmm ok? We’ll see. But, in practice, I was absolutely blown away. There was the first answer, which was easy and surface. Then the second answer, which went a little deeper. And then, the third answer, which felt like an answer I didn’t even know I had, but which needed space and time and some “digging” to come to the surface.

It had me thinking — how much is right below the surface (or perhaps the second or third layer of the proverbial onion) that we aren’t sharing with our partners or closest people because a) we’re not asking in the right ways and b) we don’t give/have the space and time to explore the ‘third’ version of our answer.

I am chuckling to myself as I type this because my sister (who is also a therapist) sometimes will ask me “no, but how are you really?” It comes after I’ve probably talked her ear off on the phone about how busy I am and whatever else is top of mind. She is one of those people who has the superpower of spaciousness and can get to that third answer on a regular basis - how are you?

If I’m being totally honest, I sometimes bristle at the question. As a working mom of three (despite being a therapist!) I don’t always have the bandwidth, or frankly, the desire, to go to a deep place of vulnerability and reflection at any given moment.

however! I do think many of us are craving depth and vulnerability (at least, in certain moments.) I think many of us feel lonely in our relationships, or that the relationships which should be our closest ones, feel surface and lacking. So, if that is you, you are not alone. I meet with individuals and couples every week who are exploring this very topic — how do we deepen our connection? how do we feel more connected in our relationships (romantic, platonic and/or familial)?

I wish I had a universal answer to these questions — obviously, I do not. But, here are some ideas for small ways to lean in with your people.

Give yourself the challenge of asking (at least) 3 follow up questions when you are in conversation, before immediately switching to your own stuff. Show engagement, active listening and curiosity. Stay in it for a little longer than you normally would & see what happens.
don’t bring your phone to the table or to bed;
- I have this conversation a couple of times a week, at least. Couples who are wanting a deeper connection - be it, emotional intimacy or more sex in their marriage, but then they are distracted by their phones at date night or get in bed and escape into a screen. It is a simple issue, not an easy one.
- Many of us are suffering from severe phone addiction and don’t even realize the impact it has had on our lives or our relationships. I know a lot of us are thinking a lot more about how to create these boundaries and break this cycle.
don’t wait for someone to ask. it is ok to send a text and say “it’s been a hard week” - let people show up for you; they can’t support you, if you don’t tell them you’re struggling.
- I had a brutal week last week; I was solo parenting, and there were a number of things that hit all at once — texting my girlfriends, who live all across the country, and feeling their words of love and support was like a hug from afar. It didn’t solve anything I was going through per se, but it certainly helped me feel less alone.
  source
my family has been using these cards at dinner time & it’s become a favorite little moment of connection. The questions range from “would you rather have glitter all over your hands or syrup on your face?” to “what is something you love about our family?” —
- my two year old isn’t exactly engaged in the conversation, and my five year old often provides an answer eerily similar to that of her eight year old sister, but the tradition of slowing down at the end of the day to ask each other questions feels like a great place to start.
- Other games like Esther Perel’s card game, or We’re not really strangers are great for grown up conversations. They usually have special decks especially for couples, too.
ask your people what they are reading (or watching!) I recently read The Correspondent by Virginia Evans, and it blew me away. One of my favorite parts was the letters the protagonist and her best friend exchanged over the course of 5 or 6 decades - always with a post script on what book they were reading at the moment they wrote the letter. I feel like its such a lovely way to know what is on someones mind… just like, admiring someones bookshelf when you come into their home. It tells you so much about their inner world.

What are other ways you find the space and time to connect with your people? I’d love to know.

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