Fork and the Road
Meet up location based on bike tour
If you and your date are the type who just can't sit still, a Fork and the Road culinary tour is the ticket. Meet your date at the first stop on your tour to begin your pedal-powered, food-based adventure led by local biking enthusiasts/dining experts. Tours vary in duration, miles covered and times of day, and you can rent a bike from the first stop or just bring your own. If the date goes well, you can return to one of the spots you explored for date #2.
Location based on category chosen
For the endlessly curious, Dabble is something of a first-date dream. Cheap, timely and educational, you can sign up for a class that's of mutual interest to you and your date and try your hand at something new. The classes are small and intimate and allow you to explore anything from pasta making to photography to introductory welding in what are usually 90 minute to 2 hour long one-time classes.
1122 E 87TH St
Chicago, IL 60619 (773) 221-2600
Though plenty of folks haven't laced up a pair of skates since the sandbox days, roller rinks around the city are packed—with adults, no less. In Chicago, Jamskating (think hip-hop fueled break dancing meets roller disco gymnastics) is particularly popular, and The Rink is one of the best places in the city to see this kind of footwork on wheels. One of the last roller rinks in the city, this far South Side rink offers nights for adults only, instruction and the always-popular Thursday night "Midnight Smooth" with old school R&B jams aplenty. Besides, if you're new date can fall on his or her butt and laugh it off, you know you've found a keeper.
Old Town School of Folk Music
909 W Armitage Ave (at N Bissell St)
Chicago, IL 60614
Every first Friday of the month, the Lincoln Square location of the Old Town School of Folk Music opens up jamming, dancing and mixing. You and your date can bring some instruments to join a folksy guitar jam session or drum circle, or slip on a pair of dancing shoes to give Zumba or Square Dancing a turn. If active listening is more your speed, the centerpiece of each First Friday is a feature performance by a member of the talented OTSFM faculty. The facility's cafe is open, too, so you'll be able to pass the evening with a little libation.
Chicago Golden Gloves
Chicagoans love a good fight—so long as their date isn't the one throwing punches—and the Windy City is home to some of the best Golden Gloves fighters in the Midwest. Spry, young fighters have been duking it out for the Golden Gloves title for more than 90 years, so if you're looking for a date pick that's a true Chicago institution, you won't find one much better (or more exciting) than this. The action-packed bouts are lively and fun and always attract a spirited but amiable crowd. If your date is particularly adventurous and doesn't mind a little sweat or blood spatter with their popcorn, a pugilistic-themed date will be a one-two punch success.
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