“I had fun” is harmless, which is exactly why it disappears. A better first message opens the little argument they left on the table: whether the pianist butchered the last song, whether the tiramisu was overrated, whether she was right about that old film.
The point is not to perform cleverness. It is to make the next reply feel like the date never snapped shut at the curb. She can disagree, tease him, or send one laughing correction without having to decide what the whole evening meant. That low-pressure lane matters after forty, when people have plenty of practice spotting a line that is trying too hard. If she adds a detail he forgot, she has reopened the door herself.