Cities as big as Chicago have infinite possibilities for dates. This list might help you narrow down the choices. Remember, no matter where you choose, things will turn out better if you manage to relax, be yourself, and have fun.
Bourgeois Pig Cafe
Unless your date already knows “The Pig,” test his or her sense of humor by suggesting the two of you eat here. By the time you’ve finished, your date will compliment your good taste.
Bourgeois Pig Cafe Founder F. Mason Green used his memories of traveling and working in Europe and San Francisco to conceptualize this casual café. The result is a menu full of fresh sandwiches, salads, drinks, and an extensive bakery on the premises. Bring mugs for the two of you and get props for your thrift, there’s a small discount on drinks if you do.
The Second City
Who can resist a good laugh? Bring your date to the place that has tickled funny bones since 1959 and gained international acclaim for its successful Saturday Night Live stars Dan Aykroyd, John Belushi, and Gilda Radner. Gogobot members disagree on Second City’s food quality and chair comfort, but they agree that it fulfills its main mission, making people laugh, night after side-splitting night.
Old Town School of Folk Music
Does your date brag about having musical talent? Make him or her prove it at the First Friday Open House on the first Friday of each month. While Old Town School of Folk Music caters primarily to folk and acoustic musicians, you can check the calendar for open jams in other styles. You can also attend to listen or dance. Are you and your date ready for a longer-term commitment? Sign up for a class together.
Museum Campus in Grant Park
Combine your love of the outdoors with your intellectual side in the southeast corner of Grant Park. It includes plenty of space for a picnic, walk, or view of the lake as well as three of Chicago’s leading museums: the Adler Planetarium, the Shedd Aquarium or the Field Museum of Natural History. Get some insight into your date’s interests by letting him or her pick the museum.
The Library at Public Chicago has a dual identity. By day it’s a coffee bar that caters to the business crowd, offering a variety of coffees and pastries for people to enjoy while using oversized tables to work or meeting in front of a roaring fire. By night, the Library becomes a lounge that offers an exciting collection of domestic and international beer, wine, and gourmet foods.
For a date that challenges the mind and supports conversation, try Guthrie’s. This Lakeview bar features a full selection of beer, wine, bar food, and board games. It’s a great way to get acquainted on a competitive level while enjoying the open-air back porch. If Guthrie’s is truly a place where “neighbors become friends,” it has a lot of potential for dating couples as well.
There are plenty of other choices for dating in Chicago. Where did you have your best date? Where did you have your worst? Share your experiences and recommendations.