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Make a date jar without losing the paper slips
A date jar is a stupidly good idea. You write plans when you're in a good mood, and you pull one when you're not. The failure mode is paper: slips get lost, the good one is always at the bottom, and one of you becomes the archivist.
Frasco is that jar on both phones. Eat, do, and watch stay in separate piles so dinner doesn't lose to “we should go out.” Surprise ideas stay hidden until they come out, which is the whole point of planning something for the other person. If the pull is bad, “Another” is right there. The jar will get mouthy. It will not force you.
Start with nine ideas you would actually do, not nine ideas that sound impressive. Breakfast for dinner counts. A walk counts. The movie one of you has never seen counts.