We're the date night planning service that does the work for you. Answer a quick questionnaire. Get a completely personalized date night itinerary within 48 hours. Then you just show up and be the hero. The perfect date night done right.
One of these people is having the night of their life using our custom date night planning service. The other is eating breadsticks alone wondering where it went wrong.
Fill out our quick 2-minute questionnaire. Budget, vibe, city, occasion — we handle the rest.
Amy personally researches your city, makes the reservations, contacts the vendors, and arranges every detail. All done for you by a real human who genuinely cares about your night.
Everything is handled. Reservations made. Vendors coordinated. Your confirmation lands in your inbox within 48 hours. You just show up. For peak season weekend reservations at the most sought after spots, we recommend booking at least 2 weeks out so we can secure exactly the right table for you.
Here's an example of what lands in your inbox from our date concierge service — every detail of your personalized date night handled.
Every plan is built specifically for you — your city, your budget, your vibe.
We offer custom date ideas and romantic planning for every kind of night. From fun dates to adventurous experiences to romantic evenings, you just tell us the vibe and we'll create your perfect date night itinerary.
Every plan comes with more than a list of places. It comes with the details, the research, and the thoughtfulness that turn a good night into one they will never forget.
Choose the plan that works for you. No stress. No guesswork.
Just show up.
One fully custom date night plan built around your person, your occasion and your vibe. Research done. Details handled. You just show up.
One custom date night plan every month, automatically. Cancel anytime — no questions asked.
Full concierge service from start to finish — every detail handled, every surprise arranged.
All plans include Amy's insider Naples knowledge, local vendor relationships and the guarantee that your partner will be impressed.
Questions? Email amy@bookeditlikeaboss.com
We're your romantic date planner in 8 major cities. We know every city like a local — hidden gems, best kept secrets, and spots that make them say "how did you find this place?" Whether you're looking for date night ideas in Naples, FL, Miami date planning, or adventures in any of our cities, we've got the insider knowledge.
Don't see your city? Request it →
Everything you need to know about our custom date night planning service.
Fill out our quick 2-minute questionnaire telling us your budget, vibe, city and occasion. Amy builds your completely custom date night from scratch and delivers everything straight to your inbox within 48 hours. You just show up and be the hero.
Yes, completely. Amy personally makes the reservations, coordinates with local vendors, researches what is happening in your neighborhood that night and arranges every detail before you leave the house. You do not lift a finger. You just show up.
We want you to be thrilled with your night. If something does not feel right just reach out and we will make it right. Your night matters to us as much as it does to you.
We currently plan dates in Naples FL, Miami, Boston, New York City, Nashville, Chicago, Los Angeles and Dallas. Do not see your city? Request it and we will let you know when we expand there.
Most plans are delivered within 48 hours. For weeknight dates and off-season timing that works beautifully. For peak season weekend reservations at the most sought after spots in Naples and beyond, we recommend booking at least 2 weeks out so Amy can secure exactly the right table. And if you need a plan today our Date Rescue add-on gets you a full itinerary in 2 hours flat. Just order by 6pm.
The Stay Booked Monthly Membership is $90 per month and gets you one fully custom date night every single month, automatically. You never have to think about date night again. Priority planning, faster turnaround and seasonal event integration are all included. Cancel anytime, no questions asked.
Not at all. We plan dates for couples, first dates, anniversaries, proposals and anyone who wants to show up and make a great impression. If you are trying to create a memorable night for someone special we have you covered.
Google gives you the same list everyone else gets and AI gives you a generic template. Amy gives you a night built specifically around your person, your budget, your city and your occasion with real vendor relationships, real reservations already made and insider knowledge no algorithm could ever replicate. There is no comparison.
I am the expert so you don't have to be. Because at the end of the night, your partner isn't thinking about the planning — they're thinking about you. That's my expertise. That's my edge. That's Booked It Like a Boss.