Plans & Pricing

Free to start. Premium for endless date nights.

DateDash AI is free to use — no credit card, no signup required. Premium is now live — unlimited plans, deeper personalization, and an ad-free experience.

Free
$0/ forever

Everything you need to plan a great date night tonight — no credit card, no signup wall, no friction.

  • ✓ AI date night plan generation
  • ✓ Real Orlando, Tampa & Winter Park venues
  • ✓ Booking links & travel time estimates
  • ✓ Save & share your plan via link
  • — Ad-supported browsing
Feature Free Premium
AI plans per monthGenerate fresh date night itineraries from your vibe and budget. ✓
Monthly quota
✓
Unlimited
AI personalization depthHow well DateDash tunes recommendations to your past picks and feedback. ✓
Per-session
✓
Learns over time
Swap & regenerate stopsReplace any individual stop in a generated plan without rebuilding from scratch. — ✓
Save plans to your accountKeep plans in your dashboard so you can revisit, edit, or share them later. ✓
Up to 5 saved
✓
Unlimited
Custom city targetingPlan for any custom neighborhood, day-trip city, or off-list destination you choose. — ✓
Ad-free experienceNo banner or sidebar ads anywhere on the site. — ✓
Priority supportSkip the queue for bug reports and feature requests. — ✓
Booking-link click trackingPremium booking-link clicks are logged for admin reporting; customers do not have a tracking view in their dashboard. — ✓

Premium questions

Is Premium worth $7.99 a month?

If you plan dates regularly, one monthly subscription adds deeper personalization, stop swaps, custom-city planning, ad-free browsing, and priority support.

What does the Free plan leave out?

Free includes AI plans, real venues, booking links, and travel times, with a monthly generation quota and ads. History-based personalization, stop swaps, custom-city planning, and priority support are Premium features.

What happens when I upgrade?

After Stripe confirms checkout, Premium is applied to your account. Your existing saved plans remain in your dashboard.

Can I cancel Premium or ask for a refund?

Premium is billed monthly. For cancellation or refund help, email hello@datedashai.com.

What happens to my plans and bookings after I upgrade?

Your saved plans stay in your account. Booking links send you to the venue or booking partner to make a reservation. Premium booking-link clicks are logged for admin reporting; customers do not have a tracking view in their dashboard.

Free Personalized Plan

Get a date night plan built for Orlando — in 10 seconds

Enter your email and we'll send you a personalized itinerary based on your vibe and budget.

No spam. One welcome email with your plan, then weekly date ideas.

Ready for a great night out?

Set your vibe, budget, and location. Your personalized date plan is 30 seconds away — completely free.

Plan Tonight's Date →
Don't Leave Empty-Handed

Get a free personalized date night plan for Orlando →

Tell us your vibe and budget. We'll build a complete evening itinerary with real venues, times, and booking links.

No spam, ever. Unsubscribe with one click.