This Story Will Make You Stop Saying “I Hope You’re Well” Ever Again

The words we use to express closeness and care in our culture can drive us further apart. Is it respectful detachment or a hesitation to share true feelings?

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On the day my grandmom died, I went for a walk to clear my mind. As soon as I started walking, the sidewalk seemed like a conveyer belt that was moving faster than usual and I had no way of stopping it. The small red leather purse I carried with me that day was a gift from her. The bag only weighed a few pounds with a thin strap slung across my chest but it felt like I was dragging heavy luggage, luggage filled with the layers of feelings I couldn’t articulate. I was confused, I knew crying could be healthy, but I just walked.

I passed a grimy looking 7-11 I’d never seen before and had a bizarre craving for a ginger ale from the soda fountain. The first sip, tasted like it had a splash of acetone. As I was chucking it into a nearby trash can, I spotted Mary, a neighborhood friend, who saw me too and gave me an excited hug. She asked how I was, her voice bouncy and exuberant. Instead of answering, I asked her what she was up to. She’d just left yoga class. She asked again how I was. “How are you” is a question that, in an instant, can turn meaningless or meaningful, depending on how you answer it. I considered going the meaningless route. I could say, “Fine! Just talking a walk!” Then I remembered that this is a friend from church. We once celebrated a birthday together. Another time, we co-hosted a party together. Maybe I could lean on her for emotional support? I explained that my grandmom died and I was feeling in bad shape emotionally.

Mary expressed kind regards. Then she asked the question everyone asks when you tell them someone died: “Were you two close?” It’s grief’s social census report. It’s the principal line of inquiry that determines the appropriate size someone’s sadness can take. The answer to this question is rarely binary and depends on how someone defines closeness. I tend to feel close to people I can have heart-to-hearts with. Grandmom wasn’t really one of those people. We didn’t have deep conversations. We did, however, smoke cigarettes together, during my rebellious phase, which she seemed to wholeheartedly support. For fun, she often sang the lyrics to Rod Steward’s “Do You Think I’m Sexy?” It was common practice for her to slip me $20 bills. She “treated” me to clothes at Macy’s, always with at least two coupons and her discount membership card. She loved to gossip, gamble, and shop. When my friend asked if we were close, would the time my grandmom bought me a pair of clunky clogs from Bon-Ton for no reason qualify? (It was the late ’90s, I was 15, and all I wanted was trendy backless footwear.) What about the time she took me took me to Atlantic City? Does that count? I nod to Mary and say, “Yeah, we were.”

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She nods back, playing her role in the cultural script we all know. Here was Mary, on a breezy walk home and not really prepared to come face to face with me in teary meltdown mode on the street next to a trashcan outside a 7-11. When I’m overwhelmed by sadness, it’s always the first time I admit how I’m feeling that the crying starts; it’s as if the other person’s query is a rope on a bucket, pulling the sadness out of a deep well, reshaping the emotional flatness that defines ordinary daily life. Mary gathered information about the funeral arrangements, then we parted. Seeing her was a catalyst to my quickly getting in touch with my grief, but it also made me fearful of future strained conversations and clichéd phrases repeated back and forth that created a personal inward spiral of emotions in me.

Later that night I texted my poet friend Roger to tell him what had happened and I asked him to keep my family in his prayers. I expected a text back with lines of sympathy and the prayer emoji. Instead, the phone rang. Soon he was asking me what my favorite song was. I thought he was trying to cheer me up by talking about music. This approached surprised in a good way, but I couldn’t think of a song. While I hesitated, he started singing the hymn, “It Is Well With My Soul.” He finished the song and prayed for me over the phone. I cried again but this time the tears were cleansing, as if our call was spiritually synched. I didn’t share stories of my grandmother or try to explain my complicated emotions over the phone. When someone’s suffering, God should send poets to sing to them.

Recently I found myself reaching out to an old friend who I sensed might be going through a tough time. I found myself wanting to end my note with, “I hope you’re well.” What I would really be saying is, “I’m concerned—a part of me is yearning for the past where I could be a part of this experience with you but instead of extending my hand I’m extending my hope. Probing any deeper feels scary, but I want you to know I care.” I wrote a lighthearted joke instead.

I’ve come to linger on the phrase, “I hope you’re well” and I wonder what we are really saying when we use it. We live in a culture where friendliness is expected. When we send a business email, we say we hope the other person is doing well. I’ve used this phrase hundreds of times and in it I may be saying, “I need your help,” or “I want you to consider my idea,” or “I want you to choose me to work with you and I also want you to know I’m a considerate human, even though we don’t really know one another.” Courtesy is generally good practice, but it can’t compare to personalized, thoughtful communication. And that kind of pat statement really has no place if you want to make a real connection. The exchange of pleasantries can slow the development of new friendships, deflate family interactions, and even undo bonds that were once intimate.

A person in my life, someone who is more than an acquaintance but not quite a friend, texted me, “I hope your weekend is going well!” From her message, I got the sense our semi-friend state was enough; she may not have the capacity to handle openness from me, or to open up herself in a vulnerable way. Not only do we hesitate to share our feelings, we are also somewhat resistant to actually hearing and sharing our inner worlds. On social media, we dutifully report on how an experience went—often with emoji. We call it sharing. Then others “like” those experiences. How often do we really take part in each other’s lives? Cool detachment is intimacy interrupted, paused, altered, and even ruptured. Maybe that intimacy never forms in the first place. If each of us is always hoping the other is well, will we ever discover the truth?

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