Think of a "date" as a series of vignettes, with each piece providing a different edge or angle to the day/night. Each vignette should be planned for 45-90 minutes, with the opportunity at the end to either continue on or cut the date short. Also read Bang, it discusses this in detail. A typical good date for me involves ~4 location bounces: drink->ice cream->drink->my car->her place. A date that just doesn't take off is a 45- or 90-minute investment, since you can cut out at any of the bounces.
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