Dear Urban Diplomat: is a Summerlicious meal suitable for a first date?

If you show up in a bespoke suit and a Boxster, yes. If you show up in a Moore’s two-for-one special and a rusted-out Tercel, it’s forgivable, but barely. Even if she doesn’t label you a tightwad, she’ll be underwhelmed by your lack of panache. Summerlicious restaurants are crowded and the service is notoriously harried—great for, say, the 25th date, when you’ve entered the track pants phase of the relationship and your date night conversation largely consists of complaining about the service anyway. For a thrifty first date, pack a romantic picnic and put the money you save toward a good bottle of wine.

Send your questions to the Urban Diplomat at urbandiplomat@torontolife.com