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Relationships
How to Have Deeper Conversations With Loved Ones
It's better to talk five years too early than one day too late.
Posted November 22, 2022 Reviewed by Ekua Hagan
Key points
- "First conversations" are talks with important people in your life, with an eye toward greater intimacy and authenticity.
- One doesn't need to be facing death in order to open up deeper conversations with friends and family.
- Sometimes, to increase closeness, people need to first talk about the distance between them.
I recently led a weekend group therapy retreat for seven people who have terminal cancer. It was my role to facilitate conversations about making meaning out of life, confronting death, improving communication with friends, family, and medical personnel, and discussing coping strategies, among other topics. Yet, even though I was the leader, I felt in many ways like a student.
So much can be learned about life by contemplating the end of it. All the retreat members were in continual contemplation, each gaining deep wisdom in the process. And I did a lot of listening, soaking up their insights about how to live better, with a more authentic and deeper presence.
One particular gold nugget I knew I wanted to put into practice immediately.
Talking on a deeper level
One participant shared about engaging in many “first conversations” with friends and family since his diagnosis. He called them “first” because he was telling them about his late-stage cancer for the first time. He was clear, however, that these were not final goodbyes; rather, they were brave, awkward, intimate conversations that paved the way for a deeper series of hellos. These talks were revitalizing his relationships.
It’s easy to take life and time for granted, especially if you don’t have a terminal diagnosis to continually remind you that your time is limited. Because many of us live in a haze of denial about our own mortality, we don’t have deep conversations about life with the people we love. We talk about sports, TV shows, and the weather. But how often do we really talk on a deeper level? I, for one, don’t do it nearly often enough. And I want to change that.
What exactly are first conversations?
First conversations are talks with friends, family, or other important people in your life, with an eye toward authenticity. You don’t have to have a terminal illness to embark on first conversations. Think of them as opportunities to tell your loved ones how special they are, what you love about them, how much you’ve enjoyed your times together, and how much they mean to you. They can also be hard conversations—for example, telling a loved one when you’ve been hurt, opening up to repair and healing for yourself and your relationship.
Upon leaving the retreat, I called my mom. When she answered, instead of saying hello and launching into a saga of my latest and greatest, I simply said, “I love you.” It’s not that my mom and I don’t say “I love you” to each other often, but we don’t begin conversations with heartfelt declarations of love. I could hear a softening in her voice as she returned the sentiment. We then talked with an extra degree of ease and openness.
In addition to our own denial of life’s fragility, I think we all often forget how vulnerable we are, and how hungry we are to connect through that vulnerability. First conversations can connect us with a depth that feeds us, tends to our existential loneliness, and comforts us as we contemplate the finite quality of our lives. It can also transform relationships—even ones we take for granted.
How to begin your first conversations
Before you have any first conversations, have a conversation with yourself. Spend some time reflecting on your relationships. Perhaps take a long walk while you think and reflect. Or carve out time to journal and make note of the relationships that deserve celebration. Recall times you went out of your way to help out a friend or family member and experienced their reciprocity. Give yourself time and space to be with the joy and appreciation you’ve experienced in these relationships. Then think about how and when you’d like to have first conversations with these people.
You may realize that some of your first conversations need to be hard conversations. Sometimes to increase closeness, you need to first talk about the distance. You may need to tell someone how they have hurt or disappointed you. These first conversations are just as important as those sharing your appreciation.
Here are some ways to address these harder first conversations. You might say, “I feel a distance between us and I don’t like it. Can we work on our relationship?” Or “I was hurt by something you did (or didn’t do), and I’d like to work through it with you so we can be close again.” I encourage you to approach these conversations in a collaborative manner, knowing that both of you need to have a voice. It may take many talks to reach true healing, but the first conversation is a powerful beginning.
I want to add that you may need to keep some of your first conversations to yourself or your journal. The person you wish to connect with may be unable to hear you. Or the relationship may not be a safe place for the vulnerability of these talks. In such cases, connecting with the hurt parts inside you is best done as a solo task for now.
Never too soon
The purpose of first conversations is rooted in the truth that we have a finite time here on earth, as do all the people we know and love. Members of our retreat repeatedly pointed out that it’s better to have these talks five years too early than one day too late. As we head into the holiday season, I would suggest that this is an auspicious time to begin practicing the skill of first conversations.
