Living in a City Means Meeting in the Middle
Question: I asked a girl out on a date to see a play. Should I pick her up or meet her there? I live in New York City and we're in different neighborhoods (I'm on the West side and she's on the East).
Answer: Meet her there. Picking her up is a thoughtful notion, but you're in NYC, not Des Moines. The "pickup" doesn’t make sense in cities whose inhabitants are largely car-free and scattered throughout different areas.
If she lived en route to the theater and you were taking a taxi, then I'd say yes, by all means, scoop her up on your way. But you don't. You're on opposite sides of Midtown, in fact.
Traveling the extra mile (literally) to fetch her may cause more inconvenience than less. The pickup would be subject to traffic delays and a barrage of texts as you coordinate pickup. Plus, she may be coming straight from work or the gym. Or, if this is your first date, she may not want you to know her exact address just yet, you crazy stalker.
Your thoughtfulness need not be fully abandoned, though. You can (and should) offer to drop her off at home after the show. If she accepts, then you'll know it's going well.