The Lost Art of Making Plans

A friend recently shared that she and her family were visiting her parents, who happen to live within a 2 hour drive of me. She asked if I might be interested in driving up to hang out for a few hours over the long weekend. I was. With just a day’s notice, we inched through Chicago’s NASCAR weekend traffic for a day trip to Wisconsin. 

Our kids rode their bikes around the marina and gleefully slurped dripping ice cream cones from their tiny sticky fingers. We belted out show tunes in a park gazebo as our toddlers danced around us in circles. We walked for miles behind our kids, who were scurrying along on their scooters and balance bikes. In between shouting for them to stop whenever an intersecting street rudely interrupted our sidewalk path, we caught up on both the significant and the mundane. As dusk settled in and the stars put on the most spectacular show across the velvety blue-black sky, her family fed us a delicious dinner and sent us home with a box of freshly picked produce. 

Five hours in traffic for a six-hour hang? Count. Me. In.

People often have the perception that I am hard to get a hold of — a perception I have admittedly worked very hard to cultivate after years of making myself far too available to too many people. But truthfully, nearly anyone I care about who makes an effort to hang out with me has a 95% chance of me saying yes, schedule permitting. As the actress Emilia Clarke once said, “I always love the doing of things.”

I love hanging out, touching grass, and being in the precious company of people who make me think and/or laugh. I love doing nothing together, lazily wandering familiar streets together, running errands together, or having new experiences together. I love the surgical precision and frenetic energy of a 90-minute playdate as well as the drawn-out, dreamy quality of a multi-stop hang with a bestie that starts off with brunch and somehow ends at 2am with a sleepover. 

But ever since COVID robbed us of the illusion of certainty about our futures, I’ve noticed that folks are having a hard time making or keeping social plans. There are memes all over the internet about the relief people feel when plans are canceled at the last minute. The joke seems to be that none of us wants to get off the couch for anything, even finding love. Apparently, interacting with our colleagues, cashiers, and Amazon delivery drivers is all the “peopling” we can handle in a day. The punchline is that we are all so burnt out and exhausted from economic collapse, witnessing genocide, and an increasingly volatile political climate that we would rather re-watch The Office alone for the 61st time than have to muster up the resilience needed to face the unpredictable world that awaits beyond our weighted blankets. Layered on top of this is also what I call the Yelp-ification of the human experience — a chronic need to optimize our time by confirming that an experience will 100% be worth it (4.5 stars and above please!) before agreeing to try it out ourselves.

When you really think about it, it’s not actually that funny after all.

At any given moment, I have half-plans loosely floating with 3-5 people. Half-plans are an expression of a desire or intent to connect, without the commitment. Half-plans open a window of opportunity, but often fail to materialize because of poor communication or lack of follow through. Half-plans allow the initiator to signify the importance of the relationship without having to make any actual effort to maintain it. Half-plans can look and sound like: 

• “I miss you! Let’s hang soon?” 

• “What are you up to this weekend?”

• “We should link up sometime.”

• “I’m in town and would love to see you!”

To the untrained eye, these may seem like real plans in the making. But in my experience, these exchanges usually result in me sharing the times I’m free and/or the plans I already have that they are welcome to join. The initiator may “like” my message and request that we play things by ear, putting the ball perpetually back in my court to move things forward. When I offer options and ask for their preferences, I might get a half-hearted “that all sounds good — you choose!” in response.

Half-plans are marked by indecision and an unwillingness to commit to anything in the future. This provides the initiator with the cover to flake at the last minute; if you haven’t invested anything (money, time, high hopes) in the plan, you believe you haven’t actually lost anything if the plan doesn’t end up working out. This is not a moral failure or an irredeemable character flaw by any means; it's just really annoying.

Every plan needs an initiator and a closer. The initiator makes a clear ask and the closer confirms the details. The initiator and closer can be, and often are, the same person. But whenever someone else initiates, I try my best to make it easier by filling in as many of the gaps that I can. If someone expresses a desire to see me, I propose dates, times, venues, or other folks to include. If someone says they’d like to come visit me from out of town, I will offer a few weekends that I am available to host them. I’m actually totally willing to ignore the annoyance of a half-plan and counter with a real plan so that we make it out of the group chat, as the kids say. I’ve learned that if one or both parties are dragging their feet and unwilling to solidify the details, then you have failed to make plans. You’ve made a wish.

Real social plans of every size, scale, and level of formality are made up of three simple ingredients: 1) an invitation, 2) a time, and 3) a place. All three are required to confirm a plan, but when I’m feeling generous I will happily settle for someone suggesting 2/3. But initiating requires vulnerability and the risk of rejection, like everything in life worth experiencing. To propose an activity, you have to do a little bit of research and have at least some knowledge of what would work as a mutually enjoyable experience. It requires “labor,” if you consider the few minutes spent preparing to have fun a form of capitalistic exploitation. But in a world where chill is king, no-makeup makeup looks are coveted, and the mere perception of having made an effort is considered cringe, I believe that very few people want to risk appearing to be thirsty by too desperately desiring the pleasure of someone else’s company.  

Making plans doesn’t need to be complicated, overly formal, or be done months in advance to count. Here are real examples of messages I’ve received that resulted in concrete plans:

• “You home? I’m in the neighborhood if you’re down for a quick hello.”

• “I hear Sean Paul is in town tonight. Interested?”

• “I’m going to be in town this weekend. Are you and the fam free for dinner near X neighborhood on Saturday?”

• “Want to come over on Monday for a little crafts night? I bought bag charm making supplies!” 

• “I’m directing a new show this summer in New York on X date at Y theater and would love for you to come see it!”

• “Free right now for a phone call?”

These folks extended clear invitations with specific opportunities to connect at specific times. I happened to be available during the times proposed in all of these examples and was touched to even be thought of. I gladly took on the work of hosting, coordinating childcare, booking travel, or untangling my earbuds for the prospect of a good hang. Especially as a working mother who has to navigate the logistical Tetris of work travel, family commitments, and the caretaking and nap schedules of a small child before leaving the house, I am always grateful for anyone who tries to make it easy for me to spend time with them. 

What ultimately worries me about our atrophying social skills is that, at its core, community is the antidote to suffering. The world has burned many times before us and will continue to burn after our time here is done. Every generation has anxiously awaited their own apocalypse. The only way we have ever survived is together. Connection and joy remind us of what we are fighting for and that the burdens of this world are not ours alone to hold. We would be wise to prioritize making room for connection and joy in our daily lives.

I care far less about adhering to arbitrary etiquette rules than I do about us remembering how it feels to be together. I want us to note how healthy relationships can heal us of so much of the toxicity that plagues the world today. We have to consider the consequences of our individualistic culture of self-obsession, and heed Jemima Kirke’s famous warning, “I think you guys might be thinking about yourselves too much.” How can we make space in our minds and hearts to think about each other as we stack each brick that builds our daily lives? What is the true cost of not being perceived, and are we actually willing to pay it? How much energy are we willing to expend to be well?

If we’re all we got, we owe it to ourselves and each other to lean into the work of being in community right now, not away from it. We are so exhausted from being alive and bearing witness to all that that entails that the first thing we’ve cast aside is the very thing that will fortify our spirits and give us the power, inspiration, and support needed to carry on: a hand held, a primal scream shared, a shoulder to cry on.

So please, go and respond to at least one message that you’ve let collect dust in your inbox right now. Be the initiator. Or the closer. Commit to showing up at a time and a place. Turn those half-plans you have for this weekend into real plans. Trust me on this one — you won’t regret it.