Downtown dates

The (hopefully, possibly, maybe) first date
Your hot-as-hell coworker asks if you want to grab a postwork drink. You’re hoping it’s a date, but who can tell? Play your cards right and you could take this office friendship to the next level.

The meet-the-parents date
Make such a good impression they’ll overlook those compromising Facebook photos.

The get-me-out-of-the-doghouse date
You cheated (how could you?!), you forgot an anniversary (again!), or maybe your annoying habits are just too impossible to take (put the lid down and leave it down). Point is, you’re in the doghouse in the worst way. What you need is a classy night on the town—stat.

The cheap weekday date
You’ve been together forever. Tuesday-night dates are the way to break up the monotony of monogamy.

The under-the-radar, underground date
Hey, secret lovers (yeah, that’s what you are): Keep that affair under wraps with a below-ground rendezvous.

The solo date
No date? No problem. Chicago’s biggest cultural institutions give singles plenty of places to mingle.

The true bromance/girlfriends date
Sure, guys and girls can have a fine night out together, but sometimes we need to break off and do our own thing. Avoid a battle of the sexes with an itinerary that keeps everyone happy.

The special-occasion date
Celebrate those very big-deal nights with these very big-deal dates.