Oakling
Discover, Plan & Play
Free · Designed for iPad · Also on iPhone
2 Ratings
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Oakling on the App Store
Oakling helps Bay Area parents discover family activities and coordinate playdates within trusted circles. Browse 481+ curated activities — from parks and hikes to museums, classes, and weekend festivals — organized by what fits your afternoon, your weekend, or your kid's age.
Shipped
Live on iOS App Store
481+
Curated family activities
70+
Organic users from PWA era
Exploring the way to solve it.
I kept asking the same question: what would actually help parents show up for their kids? Not another list — real time together, real connection, memories that stick. The problem never changed. How I tried to solve it did. A resource site, a coordination app, and a native rebuild — each one an honest pass at getting closer.
Plai — a curated resource site
- Books, podcasts, and outdoor activity guides for families
- Validated the audience, but the wrong job-to-be-done
- Still live today as Oakling's content foundation
plaidate.site Playdates — a coordination PWA
- 70+ organic users across six months of testing
- Open invite-link model mismatched how trust works
- ~40% of the Lovable codebase was dead or duplicated
lovable.dev · playdates
Oakling — a native iOS app
- Full SwiftUI rewrite with direct Supabase calls
- Trusted Circles replace open invite links
- Shipped live to the App Store
Mapping the whole app.
I split the architecture into three views — how screens connect, how the client and Supabase talk to each other, and what needs to change before the product can scale.
Kids are playing outside less.Parents know it.
The fix isn't another app for kids. It's removing the friction for parents. Playdates die in group-chat logistics. Oakling makes organizing one as easy as accepting one.
- Unstructured outdoor play has fallen by half in a generation — to about seven minutes a day, per University of Michigan time-use research.
- Before the pandemic, 2½-year-olds passed a basic social-cognition test. After lockdowns, 5-year-olds were failing it — a UC Merced study published in Scientific Reports.
- Parents rank social skills as the pandemic's worst damage to their kids — above academics, above physical health, per Gallup.
From tabs to actual plans.
Find activities, plan the details, share with your Circle, put it on the calendar. Without switching apps or digging through group texts.
How we scoped the MVP.
We split the product into three parts: entry, core loop, and the explore-to-meet path. Dashed flows are what we cut for v1. Solid flows are what shipped.
dashed gray = not pursued for the MVP
⚖️ decisions
Four choices that shaped the product.
Family profiles, not individual profiles
Parents create a family profile with children's ages, interests, and neighborhood. You're not swiping on people — you're finding compatible families. The unit of the app is the family, not the individual.
Curated over algorithmic
Every activity in the database is hand-picked and illustrated. No scraping, no user-generated noise. Quality and trust over volume — the same editorial instinct from the original Plai site, carried forward.
Evergreen over dated
Instead of live event feeds that go stale, activities use an evergreen model. A park is always a park. A museum is always a museum. Seasonal content gets deactivated via a simple flag, not deleted — so the app always has value, even on day one with zero user-generated content.
Native over web
Six months of PWA testing proved the concept. But the experience gap between a web app and a native iOS app — in performance, in feel, in the App Store distribution model — was worth the cost of a full rewrite. Parents use their phones. The app should feel like it belongs there.
Playful, connected, together.
I designed the mark around how Oakling should feel — easy to play, easy to share, playful, and hassle-free. A meeting spot for families.
What's next
Oakling is live on the App Store. The next phase is growth
Share spots
Let every family add and share the places they love around the Bay — so the catalog grows from real parents, not just editorial picks.
Expand the Bay
Start where we're strongest, then add more cities across the region — so Oakling stays useful wherever families actually live.
Fresh, richer data
Improve search, grow the database, and keep listings current — more options for families, fewer dead ends when planning.
Pitch and iterate
Pitch to parents, schools, and community groups — get feedback in the room and improve before scaling too fast.
