Who we are
Sidequesters is where adults make real friends — small, in-person activities, hosted by members, one host plus up to four people, with no photos in discovery — profile photos stay hidden until you're in a group together. It's live in New York, Houston, Los Angeles, DC, Boston, and Chicago today.
Make it as ordinary to post "anyone want to play nine holes Saturday?" as it is to post a photo of the course.
Friendship isn't built by matching. It's built by small, repeated, in-person contact — the same few people, doing an ordinary thing, often enough that it stops needing to be scheduled. That kind of contact used to come free with a workplace, a neighborhood, a league, a church. For a lot of adults it doesn't anymore, and nothing replaced it. Sidequesters is our attempt to rebuild it deliberately.
This isn't a vibe. In 2023 the U.S. Surgeon General issued a formal public-health advisory on loneliness and isolation, putting it alongside tobacco and obesity as a national health priority. The findings are stark.
Loneliness of this kind is associated with roughly a 50% higher risk of developing dementia in older adults, and with markedly higher rates of depression and anxiety across every age group. Young adults — 18 to 29 — consistently report the highest loneliness of any cohort, not the lowest. And one analysis for AARP put the cost of social isolation among older adults at about $6.7 billion a year in additional Medicare spending alone.
Underneath the health numbers is a simpler shift: Americans just spend less time with friends than they used to. Time-use data shows in-person time with friends falling through the 2010s and dropping sharply after 2020 — the decline steepest among the youngest adults, the people who supposedly have the easiest time making friends.
So the design question isn't "how do we match compatible strangers." It's "how do we give adults an easy, low-stakes reason to be in the same place, doing the same ordinary thing, more than once."
Sources
Not a demographic — a moment. Almost everyone hits at least one of these, and usually more than once.
The empty-nester
For eighteen years her Saturdays were somebody's practice, somebody's recital, somebody's carpool. The last kid left for college in August and the quiet is louder than she expected. She's not looking for a best friend. She wants a standing Saturday-morning walk with three or four people who'll also be there next week.
The single parent
Between the job, pickup, and bedtime, his entire social life is a group chat he never has time to answer. He gets ninety free minutes on a Tuesday while the kids are with their mom. He'd rather spend them across a table from actual people than scrolling — but a whole evening out isn't realistic, and everyone he knows is also underwater.
The transplant
She moved to New York in January for the job. Eight months in, her coworkers are perfectly nice and her weekends are perfectly empty. The friends back home text less every month. She doesn't need a network. She needs someone to get tacos with on a Thursday, and then again the Thursday after that.
The newly retired
Work was where the people were — forty years of it. The pension's fine; the mornings are long. He'd host a chess table in the park in a heartbeat, or a slow nine holes, or a diner breakfast. He just never had anywhere to say so out loud to people who'd actually show.
The scattered thirty-something
Every close friend he has is from college, and every one of them lives in a different city now. Making friends as an adult feels like a skill he was supposed to pick up and somehow didn't. He wants a low-pressure way to practice: show up to a thing, be a decent hang, no obligation to be anyone's person.
The re-entry
A divorce, then a move, then a year of just getting through it. She's ready to have a life again but the muscle's atrophied and the apps all feel like dating with extra steps. She wants the version where you meet four people over a hike and nobody's sizing anybody up.
Every decision in the product follows from "activity first, small, in person, repeatable":
Sidequesters is built and live in New York, Houston, Los Angeles, DC, Boston, and Chicago — the full loop works today: discover a plan, ask to join, meet up, check in, connect. It's a small team. We're deliberately staying in a handful of cities until each one is dense enough that you can open the app on a Tuesday and find something real happening within a mile.
Live in those six cities, for now. If that's you, come see what's happening near you.
Sidequesters was founded in 2026 by a small team based in New York, with backgrounds in finance and product operations at institutional investment firms. The idea came from watching how much of adult social life disappears once work and school stop supplying it by default — and building the thing that puts it back deliberately.
| Company name | Sidequesters |
|---|---|
| Type | Consumer mobile & web app — small-group, real-world social meetups |
| Founded | 2026 |
| Headquarters | New York, NY |
| Website | sidequesters.app |
| Core offering | Host or join small, in-person activity meetups — one host plus up to four others |
| Cities served | New York, Houston, Los Angeles, Washington DC, Boston, Chicago |
| Communication | support@sidequesters.app |
| Social | Instagram · LinkedIn |
No. Sidequesters is for building platonic friendships through small, repeated, in-person activities — not romantic matching. There's no swiping, no profile photos in discovery, and groups are capped at one host plus four others, not one-on-one.
Sidequesters is live in New York, Houston, Los Angeles, Washington DC, Boston, and Chicago. We're deliberately staying in a small number of cities until each one has enough activity that you can find something happening near you most days of the week.
Judging a face isn't how real friendships start, and it's the fastest way to turn an activity meetup into something it wasn't meant to be. Before you're in a group with someone, you see their name, age, hometown, current city, and industry — not a picture. Photos only ever become visible between people who share a group or have mutually connected after meeting in person.
Every plan uses a GPS check-in (or a host-provided code) to verify you actually showed up. Reputation — things like "punctual" or "great host" — can only be earned between people who verifiably met in person, so it can't be faked or farmed.
Any member can host: pick an activity, a real location, and a time, and up to four people can request to join. As the host, you choose who's in your group — there's no algorithm assigning you to a table.
Yes — one host plus up to four others, five people total. Sidequesters is built for small, real activities, not large events.