Adulting Got You Down? Start a Day of Yes

A made-up tradition called Day of Yes brought four friends closer than ever, and cemented their life-long commitment to making play a priority.

Airbnb Magazine Editors
Airbnb Magazine
5 min readMar 20, 2019

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— Lindsey Weidhorn, as told to Erin Zammett Ruddy

When we were in our early thirties and single, my friend Lauren complained that having fun had become not that important anymore. She said she spent all her free time on dates — but that she had nothing to talk about on those dates because she wasn’t doing anything else interesting. Lauren is an indoor cat who historically says no to things, but that day she said to me and a couple of our other friends, “I’m going to have a summer of yes. You guys tell me what to do and I have to say yes!”

I told her she had to spend an entire day exploring the city with our friend Taj, who knows all the cool places to go. They ate at a funky Chinese restaurant in Queens, visited the Unisphere and toured a miniature exhibit at a museum. Later on, when they recounted their day, our friend Rob and I were so jealous. Those were the kinds of things we wanted to be doing too, but we had no one to do them with. So that’s when the four of us conceived Day of Yes, and our tradition of reclaiming joy began.

The rules: Every season, one of us takes a turn planning a day of adventure that can’t cost more than $200 per person. The planner sends out a text the day before with the meeting place, what to wear, and what time we’ll be back. None of us gets to ask any questions. And of course you can’t say no to a Day of Yes — it has to be an enthusiastic yes, a hell yes! (The only thing you’re not allowed is to choose something that will alter lives forever, like getting a tattoo or, you know, making out with someone when you’re in a relationship.) We can’t have a Day of Yes without all four of us present, so when Lauren got married a few years ago, she said to her husband, “Just to be clear, our relationship needs to allow me to do Day of Yes.” And he’s totally supportive. We also can’t add any new members, though we get a ton of requests. We tell anyone who asks that they should start their own DOY group — everyone should experience salsa dancing classes and take a pizza bike tour of their town and try their hand at archery.

Our day at Dorney Park and Wildwater Kingdom in Pennsylvania was one of my favorites. Taj hates waterslides, which I didn’t know when I planned it. He was really out of his comfort zone, but he still said yes and that was awesome. Then we went skeet shooting — a sport I do often that none of them had ever tried, but all found weirdly relaxing. We shot 18 rounds! On the way home we hit Sands Casino and actually won money on the blackjack table.

The best DOY was probably the one when we crashed a food blogger’s house party. Taj saw the party on Instagram and figured it would have good food, so we talked our way in, drank a lot of tequila, and made new friends.

Not every Day of Yes is daring. Our most recent was planned by Rob. Lauren was nervous because it was her first after having a baby, and Rob is the one who usually goes a little too far. (He once took us to an all-day dance party at PS1 in Long Island City.) He texted us to meet at the bagel store, wear athletic shoes, and bring a change of clothes plus a swimsuit. Lauren called me completely panicked. She said, “I’m gonna murder Rob. Why do we need to wear bathing suits?” We got to the meeting place and Rob said, “OK, we’re heading to a spa in New Jersey and we’re going to say yes to a chill day.” Lauren teared up, she was so relieved.

Sometimes Day of Yes is just about reconnecting. We’ve developed this crazy strong bond over the last five years, so it’s a time for the four of us to talk through whatever’s going on in our lives. It forces us to take a full day four times a year to have a good time together. When you’re a kid you think that becoming an adult means you’ll be able to do whatever you want. But do you? You grow up and you stop saying yes to these things. We don’t get a summer break anymore, but we can’t let that deter us. Lauren and I both lost our dads when we were around 30 years old. They never got to do safaris or big adventure trips or any of that bucket list stuff because they had pushed it off until retirement. We don’t want to do that. Right after they passed away, we decided to climb the Inca Trail to Machu Picchu. It sounds like we’re super badasses, but we’re not. We’re generally not physically fit at all, but we knew how important it was to find time to do this stuff.

Of course it would be easier to say no sometimes. We all have very busy work schedules, we’re all older and tired, and on a Saturday morning, if given the option to sleep in or go to a Day or Yes, I’m going to want to sleep in. But I have to say yes. And I never regret it. Being forced into doing an escape room or an art class or a crazy dance party and realizing at the end of the day how much fun it was makes you feel really good — and really grateful. As much as we plan intentional down time for ourselves, we should schedule time for joy, too. When else are you going to learn to German sword fight?

About the author: Erin Zammett Ruddy is a freelance writer and author living on Long Island. Her work has appeared in Glamour, HGTV, Marie Claire, Real Simple, Redbook, Shape, and on the Yahoo! homepage. She is a contributing editor at PARENTS where she writes about food, travel, home renovations, and, of course, kids. Follow her on Instagram.

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