The First Date: Café Benelux

Cafe Benelux’s stained wood and Lowland European decor might make you feel like you’ve flown to Europe for your date, but its reasonably-priced dishes will remind you that you’re still benefiting from Milwaukee’s affordable dining scene. And with its selection of over 250 beers, you can’t go wrong in the beverage department. Order a sampler of four tiny beers to share if you can’t decide on one. ($10-19) 346 N. Broadway // 414-501-2500

The Anniversary: Buckley’s

Small but elegant Buckley’s restaurant is located near the lake in its charming 19th-century building. With a small menu offering a variety of dishes ranging from corned beef to hand-crafted pasta, Buckley’s is great if you’re not sure what kind of food you and your date want. And you can take comfort in the fact that it’s always really good. ($10-33) 801 N. Cass St. // 414-277-1111

The Second Date: Louise’s

With its American-influence and fresh twist on Italian cuisine, Louise’s restaurant mixes the basics of Italian cooking with non-traditional ingredients. Their ravioli is always a hit, which is a great non-messy date food. But a “Lady and the Tramp”-style spaghetti meal is always an option, too.  ($10-20) 801 N. Jefferson St.  // 414-273-4224

The Double Date: Izumi’s

This cozy sushi bar on the east side is welcoming, even if you’re not so into the whole raw fish thing. Besides boasting great sushi options, Izumi’s offers a full menu of fully-cooked meals and vegetarian options. Compare your chopsticks skills and order some edamame to share while your meal is prepared. ($18-36) 2150 N. Prospect Ave. // 414-271-5258

The Weeknight Date: The Comet Café

When you are finally seated at Comet Cafe (hopefully at the counter – and it’s worth the wait), embrace the diner atmosphere while you and your date eat classic sandwiches and entrées with a twist. Order a cupcake or slice of pie to share before you leave. ($8-12) 1947 N. Farwell Ave. // 414-273-7677

The Meet-the-Parents Date: Bosley on Brady

A popular Brady Street steak and seafood restaurant, Bosley on Brady offers Key West-inspired dishes in a bright, airy atmosphere that compliments the food and adds to the Florida feel.  Order the seafood symphony (it changes nightly) and end by sharing “the trio,” which includes three tiny desserts. ($18-36) 815 E. Brady St. // 414-727-7975