HowAboutWe Updates

Free Dates to Go on in Chicago With HowAboutWe

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We’re excited to announce that HowAboutWe for Couples has just launched in Seattle and Chicago! Check out some of the awesome free dates you can enjoy in the neighborhood…


Romeo and Juliet. Antony and Cleopatra. Buffalo Wings and Blue Cheese. History’s greatest couples now have another among their ranks: Biking and Coffee. Focused on a love for both, Heritage Bicycles General Store combines Chicago’s favorite way to get around with its favorite way to stay awake. Offering a wide range of coffee and teas, as well as serving as a fully operational bike shop, Heritage encourages you to come in, relax, and look around.

Sit in this sun-soaked storefront any time of the day, and spend some quality time together to a soundtrack of slow-drip coffee and tinkering bike mechanics. Morning, afternoon, or night, you’ll both love the family-owned harmony of this bike & coffee oasis.


It’s about time you two became dance stars. On October 24th, be part of a dance revival that’s just as fun as it looks with one hour of instruction from two professionally-trained swing dancers. You’ll learn the rhythms and syncopations that characterize this carefree dance as you down a flew glasses of your favorite wine.

After you get the hang of East Coast swinging, you and your date will practice your moves at a one-hour, in-studio dance party. Get social—and perhaps a bit sweaty—while a live DJ spins a sexy soundtrack that’s chock-full of iconic swing tunes. A twirl and a kiss to the tempo of a Cole Porter classic? You can’t beat that.


Every Friday night, a bevy of saucy beauties host a burlesque cabaret that doesn’t take itself too seriously. They’re the Kiss Kiss Coquettes, and on this date you’re invited to their show. Joined by a rotating cast of off-the-wall comedians, magicians, and more, the Coquettes host a weekly night of risqué kitsch at The Greenhouse Theater.

For 90 minutes, you and your date will enjoy priority seating—front row when available—to an evening of classy striptease from a troupe that collectively boasts more than 20 years of burlesque experience. Laugh along with guest comedians and unexpected juggling acts, and frolic into the night feeling frisky.


Autumn air and hot apple cider bring back a sense of nostalgia that’s perfect for a day of outdoor flirting. On this date, you’ll relive childlike fun together at All Apples Orchard in Woodstock, IL, just an hour outside the city.

All Seasons boasts bountiful acres of apples, pears, and pumpkins to explore with your rosy-cheeked date. Take a wagon ride and pick a half-peck of apples to bring home, a healthy compliment to the half-dozen donuts waiting for you back at the market. Then lose yourselves in the sprawling corn maze, pet some barnyard pals, and get competitive on the pedal cart track. On the weekends, check out even more playful activities, like a shooting gallery and high-octane pig races.

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Why go to a movie theater for popcorn when you can go to a popcorn shop for a movie? Avoid the sticky floors and cell phone talkers on this date—instead, follow the delicious, buttery smell to Berco’s flagship store in Lincoln Park for an exclusive movie date night.

On Friday, October 11th, you and your date will get the royal treatment, with a screening of the classic romantic comedy adventure, The Princess Bride, two beverages total, and all the fresh gourmet popcorn you can eat. Be sure to try the “Best Caramel Corn Ever,” which is made using a secret, 15 step-process, and came after Berco’s experimented with 84 different flavors.