Plenty of things can go wrong on a first date, but pizza ain't one of them. The pizzas, wood-oven-roasted chicken wings, and desserts such as the banana-Nutella panini at Harry's Pizzeria are creatively crafted, delicious, and affordable. The restaurant's intimate space and effortlessly cool decor give the place a classic Italian vibe with a few modern touches. It's the kind of spot that feels upscale without making your wallet cry and might just persuade (or fool) your date into thinking you have good taste. Equally important is the location: It's right on the edge of the Design District, so if the chemistry is promising, you can head to the Institute of Contemporary Art up the street and continue the conversation.