1) IF YOU HAVEN’T MET THIS PERSON IN REAL LIFE YET: My recommendation is to start with coffee, a drink, or something light hearted like meeting at a park. There’s nothing worse than learning within 5 minutes of meeting somebody that you’re not a good fit, only to have to sit through a three hour dinner or sit in awkward silence next to them at the movies. If it’s going well, there’s an attraction and conversation is coming easily, you can order another.

If not, you can politely decline another round, say you need to get going, and bow out gracefully, saving you both from an uncomfortable evening. Great, it’s time to ask them on a second specific date: “There’s a concert on Wednesday/Want to grab dinner on Tuesday?

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