DateDash AI does the hard planning work so you can focus on what actually matters — each other. Here's exactly how it works, from first click to front door.
No long forms. No account setup. No credit card. We ask you three things: what kind of mood you're in, how much you want to spend, and where you are.
Choose your vibe: Romantic gets you candlelit dinners and rooftop cocktails. Adventurous brings in active and outdoor experiences. Chill focuses on low-key lounges and neighborhood gems. Foodie prioritizes Orlando's best culinary experiences including Michelin-recognized spots.
Set your total budget for two — whether that's $60 for a casual evening or $300 for a special occasion — and the AI calibrates every venue suggestion accordingly. The whole setup takes about 20 seconds.
This is where the magic happens. Our AI doesn't just pull a random list of places — it assembles a sequenced, realistic evening itinerary with venues that work together, timings that account for travel and reservations, and cost estimates for each stop.
Every venue is validated in real time against Google Places to confirm it's open, operational, and matches your criteria. We integrate Foursquare enrichment data so you also get tips, trending signals, and context from people who've actually been there recently.
For Michelin-recognized restaurants, we flag them automatically and surface the booking platform (Resy, OpenTable, Tock) directly in your plan. For experiences and activities, we surface Viator options when they add value to your evening.
Your plan is ready. Every venue has a direct action button: Reserve on Resy, Book on OpenTable, Get Directions, or Call ahead. One tap and you're set.
Want to swap a venue? Hit the refresh button on any stop and we'll suggest an alternative that fits the same budget and vibe. Save your plan, share it with your partner, or print it to the screen for offline access.
No app download required. No account needed for your first plan. Works on any phone, tablet, or desktop. We built it to be frictionless because the whole point is making your evening easier, not harder.
Plans are shareable via link — perfect for sending to your partner so they know where you're headed tonight. Saved plans sync to your account if you choose to sign up (free), so you can look back on past evenings and avoid repeating venues.
Every venue is checked against Google Places in real time. No closed restaurants, no stale data.
Plans are sequenced geographically so you're not backtracking across town between stops.
Resy, OpenTable, Tock, and other platforms linked directly. One tap to secure your reservation.
Don't love a suggestion? Swap it with one tap and get a fresh alternative that fits the same vibe.
No app download. Your plan works beautifully on phone, tablet, or desktop. Installable as a PWA.
Our AI knows Orlando's Michelin-starred and Bib Gourmand restaurants and includes them when they fit.
It takes 30 seconds. Tell us your vibe, budget, and location — and we'll handle the rest. Completely free.
Plan Tonight's Date →