If the date is going well, walk across the street to The Gage to continue the conversation. In addition to making decision-making a cinch, it’s a surefire way to learn just how spontaneous your plus-one really is.
If your date is a dog owner, head to one of the city’s many canine-friendly parks like Wiggly Field Dog Park in Lincoln Park or Montrose Beach in Uptown for a few rounds of fetch before topping it off with happy hour at Filini, where guests can bring their pups to the patio on Wednesdays for a menu featuring the likes of “Bad to the Bone Burgers” and “Frosty Paws” ice cream.
Kick off the night with a round of Chicago-style dogs at Superdawg, then make your way over to Southport Lanes -- one of the few bowling alleys that still uses human pinsetters.
Cap off the evening over hot fudge sundaes at Margie’s Candies and try to snag a seat in the famed "Beatles Booth" where the Fab Four once sat.
To ensure that you never get bored, we have rounded up 75 of our favorite date ideas.