Give love the boot at this West Town hotspot, where strong martinis (order the classic dirty Relaxer) are outshone only by the on-site manicurists (after 5 p.m.). It’s free therapy.
Beauty Bar, 1444 West Chicago Avenue, at Bishop Street (312-226-8828 or thebeautybar.com).
Let the dating games begin, literally, at this cozy Lakeview corner tavern. The selection of more than 50 classic and new board games and tiny table lamps set the scene. You quickly get a Clue whether you want to Connect Four with your date — or make a Balderdash for the door.
On the second Friday of every month, more than 30 art galleries, stores, and studios open to the public for perusing. Afterward, access your potential SO’s creative sensibilities over chorizo tacos and Mexican hot chocolate at Nuevo Léon.
Second Fridays, 6-10 p.m., in the Chicago Arts District, South Halsted and 18th Streets (312-738-8000 or chicagoartsdistrict.org); Nuevo Léon Restaurant, 1515 West 18th Street, at Laflin Street (312-421-1517 or nuevoleonrestaurant.com).
Your dating tastes have matured (in theory) since you had eyes only for Tiger Beat hotties in the ’80s. Take your date back to the future in Wicker Park, where Grand Marnier chocolate mochas mix with heated rounds of Mario Kart, Tetris, and twenty other Nintendo games.
The Wormhole Coffee, 1462 North Milwaukee Avenue, at Honore Street (773-661-2468 or thewormholecoffee.com).
Don’t get a room — yet. Let the romance build over a glass of bubbly in the sexy library. Date not much of a conversationalist? Drown out the silence at acoustic guitar sets on Wednesdays from 6 to 8 p.m.
Public Chicago, 1301 North State Parkway, at Goethe Street (312-787-3700 or publichotels.com).
Find out if you’ve met your match at Chinatown’s neon orange teahouse, where hot sesame, almond, and ginger milk teas come in oversize mugs. Grab mung bean milk shakes and iced honey black tea to go, then window-shop for Hello Kitty toys and sake cups.
Saint’s Alp Teahouse, 2131 South Archer Avenue, between Cermak Road and Wentworth Avenue (312-842-1886 or saintsalp.com.hk).
You’ll come off as cool for suggesting such a dimly lit, tucked-away place. Order cognac and lounge on a plush couch by the crackling fireplace. Sweetly seal the deal with dessert at the Chocolate Bar, set up in the hotel lobby Fridays and Saturdays from 8 p.m. to midnight.
The Peninsula Chicago, 108 East Superior Street, at Rush Street (312-337-2888 or peninsula.com).
If your date is content sharing a massive pretzel and a giant stein of German beer, you might have a keeper. Lincoln Square’s lively 40-year-old spot offers polka bands, roving magicians, dancing, and Bavarian specialties from bratwurst to schnitzel.
Chicago Brauhaus, 4732 North Lincoln Avenue, between Lawrence and Leland Avenues (773-784-4444 or chicagobrauhaus.com).
This basement-chic hipster den is home to one of the more popular Ping-Pong tables in town (test your new friend’s bar game expertise). Sunday and Thursday nights, $2 PBRs make you the cheapest date in town.
Happy Village, 1059 North Wolcott Avenue, at Thomas Street (773-486-1512 or happyvillagebar.com).
Uncomfortable first-date silence becomes obsolete when you’re surrounded by tabletop jukeboxes and silver bowls overflowing with caloric mounds of ice cream, chocolate sauce, and whipped cream at this 1920s-era ice cream parlor and confectionery.
Breaking up is not quite as hard to do when it happens at a perpetually packed bar where the bartenders are easy on the eyes. After your ex makes a run for the border, settle in solo and order enough tacos al pastor to tempt a new amigo (or three).
If the puppy love is starting to feel like a choke collar, let it loose before you go all Cujo on someone’s ass. Drop the bomb at the off-leash Montrose Dog Beach, where there’s ample space to process and start pining for a new pup.
Montrose Beach, 4400 North Lake Shore Drive, at Montrose Drive, northwest corner of the beach.
Laugh and the world laughs with you, get dumped at a legendary comedy club and you cry alone. At least your single soul can fall back on some comedic medicine. After the show, hit Old Town Ale House and clink pints with the actors.
The Second City, 1616 North Wells Street, at North Avenue (312-337-3992 or secondcity.com).
The ladies behind the window of this beloved hot dog stand have big mouths and even bigger voices. If your BF picks this place for delivering the bad news, tell the staff to serve a little verbal assault with those fries.
The Wiener’s Circle, 2622 North Clark Street, at Wrightwood Avenue (773-477-7444 or wienercircle.net).
It’s quiet, and there’s most likely Kleenex close by. Your plan for a speedy exit may be hindered by a flurry of questions, insults, or flying furniture, but at least you’ll get the job done in private.