Holiday drama, parenting a toddler, even (or especially) the Israel/Palestine conflict — these have permeated my relationships with friends and family over recent months, leading me to reflect on how (and when) we choose to have difficult conversations.
Today’s post is a longer one: a personal story, some practical lessons, and a boatload of resources from the experts.
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“There’s something I’ve been wanting to talk about…” I say as Sam and I turn onto the highway for a two-hour drive.
My timing is intentional. We’re coming back from an incredible New Year’s weekend with friends in the Berkshires, and historically we’ve had the best conversations on car rides — especially the ones outside our day-to-day.
It was during a long car ride that Sam and I made one of the hardest decisions we’d faced yet. After months of deliberation, discussion, and sometimes arguing, we decided to move from Washington, DC back to Boston. Sam could pursue his doctorate, while I was hoping for a work/life balance conducive to having our first kid.
Boston was a compromise. Sam struggled with the prospect of sacrificing the friendships and professional connections he’d made in DC for a career path as precarious as academia; I had to come to terms with moving to yet another place that wasn’t Nashville, where my family is. We spent countless hours across tens of car rides, agonizing over the decision, weighing the pros and cons, and trying to see each other’s perspectives.
“We’re stuck,” I said, over and over, and often through tears — in the car, in therapy, and in conversations with friends.
When we both finally came to terms with the move, I cheered. Boston wasn’t — isn’t — perfect, but the commitment was a relief.
What I’ve since noticed — having some distance from the decision — is how navigating this major conflict sewed us more tightly together, strengthening our bond and commitment. The conversation I introduced on Monday was of a different color — about the stress associated with parenting a newly-minted toddler, an underlying tension in our relationship — but our patterns, the comfort of being on the road, felt familiar.
We heard each other.
On Monday, Sam responded to my concerns with care and empathy — and I was able to do the same. We said things like, “I messed up…” or “You never deserve to feel like that…”
This conversation, the one along the Mass Pike, turned into (somewhat surprisingly) a beautiful way to start the year.
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It’s taken me some time to understand that having tough conversations is a skill. It’s taken me longer still to practice and hone this skill over time (I’m still a work in progress!). Here’s what I’ve learned about approaching these tense conversations in a productive — even restorative — way.
Choose your moment.
The ideal conditions for tough conversations are similar to doing anything hard: each party is well-fed, decently rested, and able to focus (read: not consumed with anxiety about something else). Bonus points if the environment is safe and comfortable (although this isn’t always possible depending on where you are and what’s happening). The car is my default for these reasons, but a long walk, your living room couch, or even a phone call can all be good settings.
I do not recommend trying to have a tough conversation when the pain is still fresh, emotions are already heightened, or when either of you are under the influence.
The most critical variable for me, however, is: am I ready to be vulnerable? If my immediate reaction to that question is anything but Yes, I can do that, I’m not ready.
Vulnerability is non-negotiable.
The breakthrough in difficult conversations usually happens when you can be vulnerable: “I was jealous,” “I missed you,” “I messed up,” or “I’m scared of losing you.”
This moment flips the script. Rather than trying to prove a point or invalidate the other person’s, I’m revealing something tender — which implies trust, changes the nature of the conversation, and often prompts the other person into vulnerability as well.
And mutual vulnerability usually gets us to the core of the issue: the reason we need to have this conversation.
Give yourself enough time (but not too much).
Tough conversations have multiple stages, so they tend to take a while. On New Year’s Day, Sam and I spent more than an hour discussing the sensitive topic I’d raised — if I’d done so at the end of the ride, rather than the beginning, we would’ve run out of time.
Here’s roughly how my tough conversations go:
The introduction of the conflict: “I want to talk about thing”
Moments of tension/discomfort: “I feel X,” “Well, I feel Y”
Meeting in the middle and seeing each other’s perspectives: “Okay, I can see how you’d feel that way”
Connection and understanding: “Now that I know this, I will…”
I’ve realized I can’t shortcut this process, or we’ll get stuck in the second stage (discomfort/tension), which, at its worst, can feel like an endless loop. When picking my moment, I aim for at least an hour.
Rather than trying to prove a point or invalidate the other person’s, I’m revealing something tender — which implies trust, changes the nature of the conversation, and often prompts the other person into vulnerability as well.
But there’s a limit to how long we can productively talk. It can be helpful to have a different activity penciled in for a few hours after the conversation — like a dinner out, a meet-up with friends, picking your child up from school, etc. — because it forces you back into your typical dynamic and helps you move on. (This is, of course, once you’ve comfortably landed in the final stage of the conversation.)
But recognize the timing is never perfect.
I’ve learned I can’t wait for the perfect conditions, or I’ll never have the tough conversation.
One sign it’s time to talk is an underlying anxiety or tension — maybe even mounting trust issues or resentment — impairing my ability to show up fully for my partner or friend. It’s a tension that, until resolved, stops me from feeling as connected to the other person as I’d like.
When I said, “There’s something I’ve been wanting to talk about…” to Sam, I knew it wasn’t just a bad day or something that had rubbed me the wrong way.
Conflict is indicative of love.
I’ve found you only have tough conversations — the ones where you’re trying to repair or strengthen the relationship — with people you really care about.
In college, my best friend and I started to drift apart. When we got together to talk about it, she said she couldn’t put anything into the relationship anymore. We’d quickly formed a bond our freshman year — staying up late into the night talking, walking home together from parties — and had supported each other through conflict with friends, graduate school applications, and never quite “fitting in.” I walked away from this conversation believing conflict in a relationship was inherently bad, and to maintain my relationships, it was important to be easy and non-confrontational.
Last year, I wrote:
A few months ago, I went on a walk with my friend Suzanne. The sun was down, and we’d just started to circle her block in the Back Bay for a second time, mutually agreeing that we didn’t want our conversation to end. At some point, the painful story of losing my first friend in college started to spill out of me: the story of getting dumped.
“It’s in the back of my mind all of the time,” I told her. “If I’d misjudged that situation so badly, how can I know I won’t do it again?”
Suzanne didn’t hesitate, immediately reassuring me of my worthiness as a friend.
Over time, with the support of friends like Suz (and books like Big Friendship!), I’ve learned the opposite. My closest relationships (with my parents, sister, husband, and friends) are the ones that have and can “hold” conflict.
These relationships are also the most fulfilling — the ones that I return to in moments of sadness and celebration.
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Think of yourselves as a team.
In the middle of a conflict or difficult conversation, it can be easy to feel like my goal is to win, to think if I can prove my point, everything will be solved. Of course, when I step back, I’m actually trying to repair or strengthen the relationship or connection.
Two people rarely — if ever! — interpret a situation the same way. The goal of a tough conversation cannot be seeing eye-to-eye — it’s to believe the other person’s perception even if you don’t share it.
I’m trying to get better at pausing mid-conversation and saying, “What are we trying to accomplish?”
Couples therapy can help you feel like a team.
One of the first times Aja and I truly connected — long before Platonic Love existed — was over a conversation having to do with the stigmatization of couples therapy. (Editor’s note: We’re both fans!)
There are times — as Sam and I experienced — when the tough conversation just doesn’t progress. Couples therapy is one tactic we’ve used to shift the dynamic: from me versus him to me and him, with a therapist.
(I wish couples’ therapy1 was just as accepted as traditional therapy has become — even for friends or non-romantic partners!)
Apologize.
Psychologists have dedicated years of study to what makes it so hard to apologize — how it deflates our sense of self, temporarily reduces self-esteem, and challenges our confidence in ourselves as decent and moral beings.2
Even when I know how important it is to apologize, the words get stuck.
When this happens, I’ve learned to lean on tactics to help ease into the apology: Laughter to bring levity to the conversation. Physical touch (with a romantic partner) to diffuse the tension and restore a sense of closeness.
My favorite tactic, though, is: the dog. When Sam and I are in a fight, we’ll (often unintentionally) use Oliver, our dog, to cut the tension: like, “Oliver says he’s sorry,” or “Should we apologize to Oliver?” Almost immediately, I feel the mood lighten in the room. It’s shockingly easier than acknowledging I did something wrong or made a mistake.
My favorite tactic, though, is: the dog. When Sam and I are in a fight, we’ll (often unintentionally) use Oliver (our dog) to cut the tension: like, “Oliver says he’s sorry,” or “Should we apologize to Oliver?”
The message is the same: I regret what I did/said/etc. and I want us to move forward together. Because I love you.
Further Reading & Listening
Each of these lessons are ones I believe in wholeheartedly; but because Aja and I are not therapists, we also turned to trusted friends, readers, and, yes (!), therapists, to help us curate a broader list of resources on communication, attachment, and conflict resolution.
📖 When I put out a call for resources for this issue, the most common recommendation was the book Attached: The New Science of Adult Attachment and How It Can Help You Find - and Keep - Love by Amir Levine and Rachel Heller. This book delves into the field of attachment, positing that in relationships we each behave in one of three distinct ways: Anxious, Avoidant, or Secure.
🎙️ Many of us know Esther Perel, the relationship expert and psychotherapist, from the popular podcast, Where Should We Begin?. If you haven’t listened before, I’d highly recommend it; in the podcast, Perel records raw, in-depth therapy sessions with real couples who are seeking help.
📰 When I reached out to my cousin (who’s also a therapist), she sent me “Letters from Esther: Could it really be that easy to resolve conflict?”. In this issue of her monthly newsletter, Perel shifts the focus towards herself, sharing how she’s learned, through decades of working with couples, to differentiate — and foster — conflict that is “productive, useful, and restorative” versus “destructive, useless, and harmful.”
📖 The bible — or at least, my bible — of friendship books: Big Friendship: How We Keep Each Other Close by Ann Friedman and Aminatou Sow. (Spoiler alert: It involves having tough conversations!) As
said, “This unforgettable book is one you will want to keep close.” And I’m looking at it now on my (closest) bookshelf.
🎙 In How to Talk to People: What Do We Owe Our Friends? from The Atlantic’s How to Podcast Series, Julie Beck and Becca Rashid delve into how a culture that prioritizes romance and family relationships can undermine our friendships. I listened to this episode several months ago, but it’s one I’ve referenced to friends on multiple occasions. It also features guest speaker Marisa G. Franco, author of Platonic: How the Science of Attachment Can Help You Make – And Keep – Friends. (One source of inspiration for the newsletter!)
🎙 Dr. John Gottman and Dr. Julie Schwartz Gottman have been researching and reporting their findings on the key to healthy relationships for more than 40 years. In this three-part interview series with Brené Brown for their newest book, The Love Prescription, the Gottmans distill their lifetime of study into smaller, daily “hacks” that will strengthen the connection in any loving relationship.
📖 Another recommendation I heard from several readers was The Seven Principles for Making Marriage Work: A Practical Guide from the Country's Foremost Relationship Expert by Dr. John Gottman.
🎙 Dr. Becky Kennedy is a clinical psychologist most well-known for her parenting advice — often told through short, digestible Instagram videos. But in this episode of the podcast We Can Do Hard Things, Dr. Becky explains how her #1 relationship strategy could be applied to any relationship — and how important it is to practice.
📖 At the start of How Not to Hate Your Husband After Kids, author Jancee Dunn’s marriage is ready to implode; so she solicits counsel from various relationship experts, applying research-backed tactics and principles in an attempt to rebuild her relationship. It reads part memoir, part self-help book, and once you get past the “click-baity” and heteronormative title, is a fun — and helpful — read.
We’d love to hear: What are the most important lessons you’ve learned — or resources you’ve found — for having tough conversations with the people you love?
ICYMI: The most popular link from Monday’s issue was the candle Sam bought Aja for Christmas — it looks like the holiday bundle is still on sale! We’ll be back on Monday. xx
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We also recognize that access to couples therapy is a huge privilege, and something that can be especially expensive when not covered by insurance.
Great list of resources - I'm fascinated by the Gottmans and their research - I fantasize about seeing their "couples lab" in person and listening in on their sessions. Learning to "do conflict
Great post and such a good reminder that relationships (friendships as well as romantic partnerships) require work and maintenance. Excited to dig into some of these resources I am less familiar with, like Big Friendship! The thing about these type of conversations that I always try to remember is that more often than not, afterwards, I feel so much better for having had the conversation. As you mention, approach it like a team. It is not ideal or fun to be in conflict with the people that we love and it is so rewarding to get to the other side of these tough moments.