If you and your date... ...have been together forever. Head to... Amelia’s Bar and Grill. You could go somewhere more expensive, but your date is a sure thing—why waste the money? Plus Amelia’s Mexican menu— stuffed quail, ahi tuna tartar, pan seared grouper—could provide some of the spice that’s been missing for, oh, the last five years. 4559 S Halsted (773-538-8200). $18.
If you and your date... ...are on your third date. Head to... Balsan. This is make it or break it time, sister! Make sure your date sticks around for a fourth by feeding him/her raw oysters, lobster and chicken fricassee, and steak au poivre. 11 E Walton (312-646-1300). Fri 11–Mon 14. $69 per guest; $36 wine pairings.
If you and your date... ...are both kind of cheeseballs. Head to... Blokes & Birds. Nothing against the place. It’s just that chef Greg Cannon has designed his three-course meal around—surprise!—aphrodisiacs. Oysters, chocolate, berries...it’s like a romance novel up in here. 3343 N Clark St (773-472-5252). Mon 14 5pm–11pm. $50 per guest; $25 drink pairings.
If you and your date... ...are engaged. Head to... Chizakaya, where you can practice sharing everything (everything, girl—are you hearing this?). Chef Harold Jurado has created an eight-plate meal that’ll involve sharing oysters, uni sushi rice risotto, lobster and checking accounts. 3056 N Lincoln Ave (773-697-4725). Fri 11; Sat 12; Mon 14. $90 per couple.
If you and your date... ...really love wine. And by “love,” you mean you kind of need it to communicate. Head to... In Fine Spirits. Chef Marianne Sundquist’s six-course prix-fixe menu includes lobster salad and red wine–braised short rib risotto, both of which can be expertly paired with wine by the nonjudgmental staff. 5420 N Clark St (773-334-9463). Mon 14 5pm–10pm. $50 per person; wine pairings, $25 per person.
If you and your date... ...don’t actually like talking to each other. Head to... Kit Kat Lounge. There’s plenty to distract you from conversation here: lip-syncing performances from the Kit Kat divas, special martinis like the “Kiss My Kitty” and dishes like mushroom-crusted Alaskan halibut. 3700 N Halsted St (773-525-1111). Fri 11–Mon 14.
If you and your date... ...only make love on locally-weaved, fairly-traded sheets. Head to... One Sister Inc, which focuses on natural ingredients for its 14-course Valentine’s dinner. The menu will be full of necessary Valentine’s edibles including oysters, king crab, chocolate and wine. Sat 12 and Mon 14; first seating at 6pm and second seating at 9pm. $110 per person. Go to onesisterinc.com.
If you and your date... ...want to get home in time to catch King Of Queens repeats Head to... Osteria Via Stato. Here, an “Italian Dinner Party” menu will be offered from 5–6:45pm. (You crazy night owls can go for the more elaborate meal, served from 7–10pm.) 620 N State St (312-642-8450). Mon 14. $38.95 per person.