Movies aren't great dates because I watch movies. What is, is something I came up with, but still haven't found a name for. It's like a road trip, but without the necessary preparation and packing. You take a road trip..around the metropolis. An 'Urban trip'?
Food detours are optional. The important part is have a sublime soundtrack setting the mood. I would suggest primarily melodic jazz pieces. Nothing supremely complicated or very atmospheric, then pepper that with some very moody melodies (I would suggest the songs Kaneda and Tetsuo) and some sing-alongs and slightly obscure music that you really really like. Again, keep the music light, but still personal.
The more important part is getting to know the other person, or other people, or getting to know them better. For example, these slightly obscure songs are sort of icebreakers and blind bets on whether there is a shared common interest.
Getting lost (or a sense of) also helps the pursuit. This whole going about late at night and just talking and revelling at the lights and architecture speaks bounds about how the other person is, at least in things I value highly.
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