Date nights fall into predictable patterns or die of decision fatigue. We’ve been to the same three restaurants. We’ve spent 40 minutes deciding what to do and run out of energy before the date started. The gap between “we should do something nice” and actually doing it is the decision, so the planner makes the decision smaller.
The first version was a Claude prompt and an Obsidian note of past dates. It now lives inside the Family Dashboard as the Date Nights tab, next to the calendar that has to have room for it.
The Board
Three columns: Ideas, To Plan, and Complete. Cards drag between columns, and moving a card writes the change back to the family’s Google Sheet, so an idea added from a phone in the Sheet shows up on the board and the other way around. A card carries the place, the date, the sitter, the cost, and afterwards a rating.
A Babysitters list sits on the same page, because a date without a sitter isn’t a plan.
Surprise Us
The dice button spins through unbooked ideas and proposes one with a vibe, an estimated cost, and a proposed evening timeline. Spin Again rolls a new one. Lock In Date moves it onto the plan. The same button shows up on the Sunday review agenda, so the weekly check-in can end with a date on the calendar instead of “we should go out sometime.”
Evening Itineraries
Any planned date can grow into a 4 to 6 hour evening: dinner, then an activity, then dessert or drinks, each stop with a time, a place, notes, and a cost. The goal is to have the logistics settled before the sitter arrives, not decided in the car.
After the Date
Completed dates get a 1 to 5 star rating, a highlight, and a “would repeat” flag. That history is what stops the planner from suggesting the same restaurant for the fourth time.
How It Connects
- Recipe Flow: the dashboard’s weekly dinner plan flags date night dinners, so nobody plans a home-cooked meal for a night you’re out.
- Budget Meeting: date costs roll into the trips-and-fun conversation in the Big 4 pulse.
- Sunday review: the weekly review has a Date Night step of its own, with the upcoming dates and a surprise pick, so the question gets asked every week.
Status
Alpha. The board, Surprise Us, and itineraries run in the live dashboard and the public demo. The board reads and writes the family Sheet; itineraries and ratings are saved in the browser for now.


