The whole night, planned in 30 seconds.
Tell us about the date in plain English. We build a complete timestamped night — drinks before, dinner, after-spot — all walkable, all bookable, all matched to the vibe you actually want.
First plan free, no signup · No credit card · Live in DC, NYC, Atlanta, Miami & Philly
How it works
Describe your date
One sentence is enough. “Second date, she likes natural wine, hates loud places, $120 budget.” Or use the chips if you prefer.
We build the night
Our planner picks the right spots from 1,200+ hand-curated venues across 5 cities, clusters them so you can walk between them, and writes you personalized reasons each one fits.
Book in one tap
Each stop has a Resy deep-link with your date and party size pre-filled. Reservation in 10 seconds, not 10 minutes.
Without DatingDex vs. with DatingDex
The old way
- 30 minutes Googling “best date night near me”
- 15 reviews that all say “great vibe”
- Pick a restaurant. Hope it's not too loud.
- Realize you didn't plan a drink before, scramble.
- Forget to book. They're full at 7pm.
With Plan My Date
- One sentence. 30 seconds.
- A timestamped night: drinks → dinner → after
- All within walking distance
- 4 sentences per spot on why it works for you
- One-tap booking, table locked in
What makes the AI different
Natural language input
Skip the form. Type what you'd tell a friend. Claude extracts the situation, vibe, budget, and dietary stuff automatically.
Personalized reasons, not canned blurbs
Every recommendation comes with 4 sentences written for your situation: tied to what you told us, with sensory details, the strategic angle, and an insider tip.
Distance-clustered itineraries
Drinks, dinner, and after-spot are picked so you can walk between them. The whole night fits a 4-block radius unless you tell us otherwise.
Post-date debrief that makes you smarter
The next morning, we email you one question. Whatever you tell us feeds your next plan. Recommendations get sharper every time you use it.
Anniversary Mode Premium
Multi-day, multi-stop, narrative-shaped plans for milestones. Friday peak romance, Saturday low-key, Saturday night the surprise. AI does the constraint solving.
Rescue Mode Premium
It's 6pm, the plan fell through, you're 20 min away. One button rebuilds your night using only what's open right now.
FAQ
What does a "plan" actually include?
A timestamped itinerary with up to three stops — a before-dinner drink, dinner, and an after-spot — chosen so they're close enough to walk between, fit your budget, and match the vibe you described. Each stop has a 4-sentence breakdown of why it works for your specific situation, what to order first, where to sit, and a one-tap booking link.
How is this different from just searching Google Maps?
Maps gives you 50 restaurants ranked by review count. Plan My Date gives you one full night, optimized for your specific situation — the vibe you said you wanted, the budget you set, the walking distances, the timing. It's the difference between a list and a plan.
How does the AI part work?
You describe the date in plain English ("second date, she likes natural wine, $120 budget"). Claude parses what you said, our planner ranks 1,200+ hand-curated venues across 5 cities against your situation, and Claude writes you personalized 4-sentence reasons each pick works — referencing what you actually told us. No generic blurbs.
Is it free?
Your first plan is free, no signup. Drop an email for a second. Make an account for a third. After that, Pro ($12/mo) gives you unlimited plans, the post-date debrief that makes your next plan smarter, saved itineraries, the printable date card, calendar export, and Anniversary Mode.
What do I actually get in each plan?
A cold-open hook to set the tone, a night-at-a-glance summary, a leave-by timing sheet with ride estimate, live weather read, a pre-date playlist, 2-3 stops each with a walk-in line, why-this-works, order-first, insider tip, what-to-wear and photo spot, a payment playbook, an if-it-goes-great extend plan, a polite bailout line, a morning-after text template, a producer’s note, a shareable date card image, a PDF you can print, and a calendar file. Every surface earns its keep.
Does it actually book the reservation?
We deep-link you straight into the booking flow on Resy with your date and party size pre-filled. One tap, the reservation page is already half-done. For walk-in spots we link you to directions instead.
How does the post-date debrief work?
The morning after your date, we email you a 15-second "how'd it go?" form. Whatever you tell us — she loved the small plates, it was too loud, you ended up walking to a third spot — feeds into your next plan automatically. Recommendations get smarter the more you use it.