Your first date was coffee. Your second was a lighthearted brunch. Now that you’re getting along grand, it’s time to step it up for date number three. Here’s a tip: Blackbird, on the Near West Side, soars ahead of its competition as Chicago’s ideal date spot for burgeoning couples—especially those fond of fine dining. The scene is low-pretense, so you won’t overwhelm your companion by going overboard with the romantic regalia, but it’s not too casual either, so you can’t be accused of being a cheapskate. Instead, the clean, streamlined interior will have you feeling sharp, modern, and excited for what’s to come. Order the tasting menu for two and unwind for a few hours as you learn more about one another. You’ll get familiar with each other’s tastes as you navigate delicious courses made with local, seasonal ingredients. Enjoy the adventure of trying something you’ve never had before, like the oxalis greens that come with the rye berries and lemon of a steak tartare. The meal culminates in a magnificent trio of cheeses, sorbet, and pastries that will seal the deal, in case there was any wavering. For drinks, there are both wine and cocktail pairings. Be adventurous and go for the latter. The bartender will work up tipples just as inspiring as the food—but remember to use your best judgment if you want date number four.