This Year, I’m Going to Plan Less

Photo-Illustration: by The Cut; Photo: Xavier Lorenzo/Getty Images

I’ve always been a chronic planner. I use date books, I bring a sweater to the movie theater, and I’ve been known to pencil “showering” into a vacation itinerary. Chalk it up to a Capricornian love for structure, a mother with high blood pressure, or just normal-person levels of anxiety — whatever the reason, I like to plan ahead. Until recently, this was never more true than when it came to social plans, for which I required at least a week’s notice — not because I have so much going on, but because I like to psychologically prepare before interacting with other people. Then I learned about the magic of the swing-by.

The swing-by goes like this: You are out on a walk, in a neighborhood where a friend of yours lives. Maybe you had a weird errand to run, or maybe you just went for a long, leisurely stroll. (Alternatively, you live near your friend — these things are a lot easier when you can bop around within walking distance of your own home.) You are feeling chatty, so you text her something like: I’m nearby — you around? Your friend may say no, which is fine — either she really is not home, or she’s not in the mood to see people. If she says yes, you’ve just arranged a low-stakes spontaneous hang. Congratulations!

Is this the fuckboy of plan-making? Yes. Spontaneous hangs are both lazy and non-committal. In many ways, that is the appeal: You are liberated from tricky dinner reservations, disagreements over who should be invited to what, and complicated route calculations. There are no fake “on my way!” texts — either you are there or you are not. I might even argue that you don’t “make” these plans; more so, you toss them into the ether with the laissez-faire attitude of a middle-aged man casting a fishing line, and sometimes a nice juicy trout takes the bait. If not, you’ve still had a lovely day out on the lake.

Sometimes these engagements end up being long — my boyfriend and I recently spent a few hours drinking wine at a neighbor’s house after popping by on an evening walk. Others are short, like a mid-workday coffee-and-park jaunt. The wide range is key. Whatever kind of hang you and your acquaintance are in the mood for at that moment, that is the kind of hang you’ll have.

If this sounds like the kind of meetup that would happen in a sitcom, that’s because it kind of is. Socializing this way is sort of cosplaying a fantasy of neighborliness and community. It’s the real-life equivalent of gathering around someone’s picket fence with coffee mugs to gossip about your fellow cul-de-sac residents. When you see someone on a whim, geography and time constraints momentarily go out the window and you can briefly live as the breezy woman about town that you very much are not.

Maybe I’m indulging my worst habits. Organizational tendencies aside, I suffer from chronic commitment issues when it comes to socializing — I’ll feel excited about something when I lock it in, but then, when the time comes to attend, find myself in a rotten mood that can only be improved by gluing myself to a couch for several hours. The spontaneous hang helpfully elides a lot of those crises. They’re painless to decline if you’re not in the mood, and later, if the urge to be social suddenly strikes, you can act on it. I know I’ll have to commit to some events (you can’t exactly “swing by” a wedding), but going into 2024, I’m going to embrace the last-minute as much as possible.

I like to explain to people that I’m high-strung because, if I let loose, things go haywire: Flights get missed, doctors appointments slide by entirely forgotten, valuable belongings get left on the train. But in the context of the spontaneous hang, being laid-back doesn’t mean being disorganized. The stakes are incredibly low. Is it a stretch to say I’ve let a little chaos into my life? You can tell me over dinner — I’ve got no plans.

This Year, I’m Going to Plan Less