Paint the Town app icon
Paint the Town for iPhone

Great dates, planned by AI that knows your taste

Tell it your city and your budget. Paint the Town researches real, currently-open venues — checking hours for your actual date, prices, and what is on that night — then hands you three complete evenings to choose from.

Free to start iPhone Lifestyle First plan free
Download on the App Store See a real plan
Your date plans

Jazz, French-Viet & Whiskey

An elegant, culture-forward evening: refined dining, intimate live jazz, and a hidden speakeasy nightcap.

3 stopsstarts 18:00~$170
18:00
90 min

Dinner at Le Colonial

3035 Peachtree Rd NE, Atlanta
~$80
19:50
75 min

Live Jazz at Kat's Cafe

970 Piedmont Ave NE, Atlanta
~$45
21:15
60 min

Nightcap at Red Phone Booth

17 Andrew Young Intl Blvd
~$45
✓ Save this plan

A sample plan, laid out the way the app lays it out.

3complete plans per tap
100%real, verified venues
~3 minfrom tap to plans
0repeated date spots

From "where should we go?" to a full evening

Paint the Town is not a list of links. Every plan is a schedule — times, durations, addresses, and costs that fit the budget you set.

1

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.

2

It researches live

The app searches the real web for venues operating right now in your city, checking hours for your date, prices, and what is happening that night.

3

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.

4

Remix and make it yours

Mix stops across plans or swap any single one, then save it, add it to your calendar, or share it with your date.

What you tell it, and what comes back

Set the vibe and the must-haves before you generate and the plans obey. These are the app's own options — tap what fits, leave the rest.

Vibe

Optional steering. The more you say up front, the less you regenerate.
RomanticAdventurousChill & cozy FancyCasualFirst dateAnniversary

Must include

The non-negotiables for the night.
DinnerDrinksLive music ActivityDessertOutdoors
Reading your taste profile…
Searching real venues near you…
Checking hours and prices…
Balancing the budget…
Putting the schedule together…

Every stop explains itself

The full evening those choices produce. Each stop carries the time, how long to spend there, the address, an honest cost, and a line tying it back to what you told the app.

Jazz, French-Viet & Whiskey · 3 stops · starts 18:00 · ~$170 all-in

18:00
90 min

Dinner at Le Colonial

3035 Peachtree Rd NE, Atlanta
~$80
Why this fits: you made dinner a must-have and set the vibe to Fancy. Refined French-Vietnamese dining anchors the night and still leaves room in the budget for the rest of it.
19:50
75 min

Live Jazz at Kat's Cafe

970 Piedmont Ave NE, Atlanta
~$45
Why this fits: you set live music as a must-have and marked jazz among your genres. Intimate room, six minutes from dinner, and it keeps the night inside your budget.
21:15
60 min

Nightcap at Red Phone Booth

17 Andrew Young Intl Blvd
~$45
Why this fits: a hidden speakeasy ends the evening on the Romantic note you set, and the last pour lands the whole night at ~$170 — inside your budget, not past it.

Illustrative sample. Real plans are researched for your city, your date and your budget.

Built for people who hate planning

The parts you would forget, or never think to check — handled on every plan.

Taste memory

It remembers where you have been

Venues from dates you have done never come back. Places you loved shape future picks; places you did not are avoided.

Weather-aware

Rain plans, automatically

It checks the forecast for your date and plans around it — patios when the evening is beautiful, cosy rooms when it is not.

Budget-honest

Priced before you go

Every stop carries a realistic cost estimate, and the whole evening is built to fit the budget you set rather than blow past it.

Swap anything

One stop wrong? Fix just that

Swap a single stop and it finds a replacement that fits the schedule, the budget, and does not clash with the rest of the night.

Book it

Reservation links on every stop

It captures each venue's real booking page while researching — OpenTable, Resy, or the restaurant's own site — so reserving is one tap.

Ready to go

Calendar and sharing built in

Add the whole evening to your calendar in one tap, or share the itinerary with your date as clean, readable text.

Partner mode

Plans that fit you both

Link accounts with your partner and every plan merges both taste profiles — nothing either of you dislikes ever gets planned.

Never forget

Anniversary autopilot

A weekly date-night nudge, and anniversary reminders two weeks out while the good tables are still open. Surprise mode shares only "be ready at 7."

Vacations

Whole trips, day by day

Point it at a destination — or let it suggest three — and it plans every day of a trip up to ten days, with lighter arrival and departure days and one merged itinerary.

Your first full plan is free

No subscription needed to try it. Every plan costs real research, so continuing runs on a membership sized to how often you go out.

Free
$0
to start
  • Your first full date plan
  • Three complete evenings to choose from
  • No subscription to try it
Basic
$9.99/mo
or $59.99 a year
  • 3 date plans a month
  • Full taste profile and remix
  • Calendar, sharing, reminders
  • Partner mode
Premium
$19.99/mo
or $119.99 a year
  • 15 date plans a month
  • Everything in Basic
  • Multi-day vacation planning

Subscriptions are billed to your Apple ID and auto-renew unless cancelled at least 24 hours before the end of the current period. Manage or cancel anytime in your App Store account settings. Venue details are researched live and can change — confirm hours and prices before you go.

Common questions

Do I need a subscription to try it?

No. Your first full date plan is free, and there is no subscription required to generate it.

Which cities does it work in?

It searches the live web rather than a fixed database, so it works wherever there are venues to find. You give it your city and it researches from there.

Are the venues real?

Yes. Every plan is built from currently-operating venues, with hours checked against your actual date rather than pulled from a stale list. Details can still change, so confirm before you go.

What if I only dislike one stop?

Swap that one. The app finds a replacement that still fits the schedule, the budget and the rest of the evening, so you do not have to regenerate the whole night.

Does it plan more than one night?

Yes. Premium plans whole vacations of up to ten days, each day researched independently, with lighter arrival and departure days and one merged itinerary you can share.

Can my partner and I share a profile?

Partner mode links your accounts so every plan merges both taste profiles, and nothing either of you dislikes gets planned.

Where do I get help?

The support page has answers and a contact address, and the privacy policy explains what the app stores and what it does not.

Stop deciding. Go out.

Give it a city and a budget, and have three real evenings in about three minutes.

Download on the App Store