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For a first date, we suggest a short plan you can easily extend. For a longer evening, combine one booked activity with dinner or a walk, taking both people’s interests into account.

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Agree on one café or meeting point. Keep a walk as an option if you both want to continue. Check the weather and your journey home; no particular city location can be assumed to be quiet or uncrowded at all times.
Start with the ticket time and performance venue, then choose a nearby restaurant. When booking, say when you need to leave. Check travel between venues on a map and allow a buffer instead of treating the shortest estimate as a promise.
Agree on a budget for both of you and whether it includes tickets, food and travel. Have one indoor alternative for an outdoor plan. A shorter evening with a clear choice may be easier than several prepaid stops.
Start with a walk and one chosen stop. Check paid activities’ prices in advance and agree on a total budget.