Chocolate might be the quintessential food gift. Depending on the packaging and quality, it can channel romance, please a party host, or disappoint (Whitman's Sampler, anyone?). To ensure we're sending the right message, we enlisted a few professionals: Le Bernardin pastry chef Michael Laiskonis; master sommelier and B.R. Guest director of wine and spirits Laura Maniec; and restaurant-logo (Sfoglia, Mermaid Inn) and food-packaging designer Louise Fili. We examined and sampled gift boxes priced at less than $50 from: Bespoke, Kee's, Nunu, Mast Brothers, Max Brenner, Fine & Raw, Jacques Torres, Tumbador, Liddabit, François Chocolate Bar, Vosges, and Chocolate Bar. The experts rated the chocolates on a ten-point system for taste, five for presentation, and five based on whether the selection makes a good gift. Find out what to buy for every candy lover this year, from a hippie sibling to an exec.