Happy anniversary to us — we're recording this one from Miami in the hotel where we took our first trip together five years ago. Jake planned the whole thing, and we almost missed the flight (not our fault!). We get into the debate that started at the airport: are you still on your parents' phone plan in your 30s? Four listener questions this week: the guy who followed you on Instagram two years after you told him you weren't a match, being 25 and single while all your friends pair off, comparing your engagement timeline to an acquaintance who just got engaged after three months, and the guy who says money is tight and all your dates are at his house — hookup or just broke?

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