
Paint the Town: Date Planning
Great dates, planned by AI
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About
Great dates, planned by AI that actually knows your taste.
Tell Paint the Town your city and your budget. It researches real, currently-open venues — checking hours, prices, and what's on for your actual date — then hands you three complete evenings to choose from. Every plan is a full schedule: times, durations, addresses, and honest cost estimates that fit the budget you set.
Pick one, remix them, or swap any single stop. Your first date plan is free — no subscription needed.
HOW IT WORKS
- Teach it your taste. A short quiz captures what you both love — cuisines, activities, music, drinks — and what to avoid. It keeps learning from every plan you rate.
- AI researches live. It searches the web for venues operating right now in your city, checking hours for your date, prices, and what's happening that night.
- Pick from three plans. Three distinct evenings, each fully scheduled and budgeted, with a note on why each stop fits you. No two plans share a venue.
- Remix and make it yours. Mix stops across plans or swap any one of them, then save it, add it to your calendar, or share it with your date.
EVERY DETAIL HANDLED
- Taste memory. Venues from dates you've already done never come back; places you loved shape future picks.
- Weather-aware. Checks the forecast and plans around it — patios when it's beautiful, cozy rooms when it isn't.
- Budget-honest. Every stop carries a realistic cost, and the whole night is built to fit your budget, not blow past it.
- Steerable. Set the vibe and must-haves — romantic, first-date casual, live music, dessert — before you generate.
- Swap anything. Change one stop and it finds a replacement that still fits the schedule and the budget.
- Ready to go. Add the whole evening to your calendar in one tap, or share it as clean, readable text.
- Reservation links. Each stop links to its real booking page, so reserving is one tap away.
- Partner mode. Link accounts and every plan merges both taste profiles.
- Anniversary autopilot. A weekly date-night nudge and anniversary reminders two weeks out, while the good tables are still open.
WHOLE VACATIONS, DAY BY DAY (PREMIUM)
Point Paint the Town at a destination — or let it suggest three — and it plans every day of a trip up to 10 days, each day researched independently, with lighter arrival and departure days and one merged, shareable itinerary.
MEMBERSHIP
Your first full date plan is free, no subscription needed. Because every plan costs real AI research, keep going with a plan that fits:
- Basic: $9.99/month or $59.99/year. 3 date plans per month, full taste profile, remix, calendar, sharing, anniversary reminders, and partner mode.
- Premium: $19.99/month or $119.99/year. 15 date plans per month, plus multi-day vacation planning.
Subscriptions are billed to your Apple ID and auto-renew unless canceled at least 24 hours before the end of the current period. Manage or cancel anytime in your App Store account settings.
Venue information is researched live and may change — always confirm details directly with the venue.
Terms of Use (EULA): https://www.apple.com/legal/internet-services/itunes/dev/stdeula/
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What's New in Paint the Town
1.0
July 30, 2026
Subscription plans
Basic — 3 date plans a month
Full taste profile, remix, calendar & partner mode.
$9.991 Month





