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Full disclosure: Rae and I ate our way through Healdsburg. We stopped at Willi's Seafood & Raw Bar, where we sipped white wine and traded notes on each oyster. Later that evening, at Hotel Healdsburg's sister restaurant, Spoonbar, we did icebreakers while sipping our craft cocktails. Some were silly (like, "If you were stuck on a desert island and could only listen to one artist or band, who would it be?") and others enlightening (for instance, "What's something I don't know about you?" revealed that Rae competed in horse shows when she was a kid, and that I taught myself HTML in junior high so I could build my own Britney Spears fansite).
Eating delicious food while sitting at a fancy, candelit table was really nice, but learning new things about each other was even better.