Jacqueline Ostrowski

Date One
It's new between you two. You’re not even sure if this counts as a full-fledged date. Take the pressure off and invite him to Lincoln Park’s hip new Argo Tea, where in addition to such inventive beverages as "teapuccinos" and tea sangria, tea ice cream is served. Try green tea, chai, or berry blast.

The chill atmosphere is conducive to conversation, and it’s open until 11 p.m. on weeknights—a nice alternative to both the bar and Starbucks scenes. Plus, you can people-watch as the usual crowd of Armitage bar- and restaurant-goers make their way down the busy block.

(Argo Tea, 958 W. Armitage, (773) 388-1800)

Date Two
You both want to see each other again, but you’re still on the fence as to exactly how she feels. Head to Randolph Street’s newest addition, avec, for an evening of tapas, wine, and plenty of witty banter. The Mediterranean-inspired hotspot doesn’t scream “date place,” but its diverse menu and mellow vibe still provide plenty of subtle sensuality. Many dishes are prepared in a wood-burning oven and designed to complement your choice of wine. And with 75 bottles of wine under $30, you can afford to spring for a bottle (or two!). A bonus: group seating means you’ll surely avoid awkward pauses, and you’ll never hurt for a new topic of conversation.

(Avec, 615 W. Randolph, (312) 377-2002)

Date Three:
Things are heating up, so plan an evening of equal parts serious dining and silly theater fare. Visit Menagerie on Belmont for American contemporary cuisine. Popular options include the rack of lamb, the upscale twist on fish and chips—a tuna maki creation—and the fondue dessert. If you start taking food—and each other—too seriously, just head across the street to catch an offbeat show at the Bailiwick Arts Center. Several holiday productions are in the works, including ‘A Merry Jewish Christmas.’

(Menagerie, 1232 W. Belmont, (773) 404-8333; Bailiwick Arts Center, 1229 W. Belmont, (773) 883-1090)

Date Four:
Impress him with your culinary expertise by suggesting newly-trendy, always delicious Korean fare for your next outing. Spicier than been-there-done-that Thai and more creative than going for sushi (again), Korean dishes will give you both something to talk about long after dinner’s over. These two spots shake up their menus with modern twists on conventional fare.

Near Northsiders can embrace the cuisine at Lakeview’s Koryo, where bi bim bop (beef, chicken or pork with vegetables served in a stone bowl) and bulgoki (marinated beef) dishes reign supreme. There’s no liquor license yet—until then, show him you don’t need a pricey cocktail to start the evening off, and amuse yourselves with currently popular Asian bubble teas.

If you’d prefer to venture further north, the slightly more established Jin Ju in Andersonville boasts inventive drinks and zesty soups in a minimalist-chic atmosphere. The most popular dish consists of spicy boneless chicken marinated with vegetables, but try the seafood tempura and the barbecued short ribs, too.

(Koryo, 2936 N. Broadway, (773) 477-8510; Jin Ju, 5203 N. Clark, (773) 334-6377)

Date Five:
You bypassed all that awkward front-door etiquette by having her stay over last night. Now it’s noon and you’re both bleary-eyed and starving…but who feels like cooking? A brunch spot would be just perfect. Feel like making the South Loop scene? Then try Room 12, a Southside outpost of Milwaukee Avenue’s Bongo Room. If you’ve patronized Bongo Room in the past, this menu will appear comfortably familiar—Room 12 offers the same eclectic fare, but without the Wicker Park address. Sample breakfast burritos or creative pancake concoctions—Ricotta ginger butter or lemon raspberry are a few options. The lunch menu has a few additions that you won’t see on Bongo Room’s menu.

(Room 12, 1152 S. Wabash, (312) 427-9972)

Date Six:
This time, you’re meeting her friends. Start out with martinis and appetizers at Wrigleyville’s Tryst, a refreshing spot amidst the area’s countless sports bars. The simple yet sleek décor complements the lounge-y atmosphere. It’s more refined than most Wrigleyville offerings, but never fear—there’s still a TV screen so you all can catch the latest game. Share a platter of prawns in these polished surroundings while you contemplate your next stop.

Spot 6, a burst of orange energy on Clark, also caters to a crowd that wants more than sports out of a bar. Stop by to dance to pop and hip-hop, and be sure to take advantage of the relatively low drink prices.

Another nearby option, Moxie, focuses more on food; menu offerings include pork tenderloin, sesame-crusted chicken, and lobster Rangoon. She can return with the girls for cosmos and Sunday night Sex and the City showings, but for a weekend, it’s ideal for both of you.

(Tryst, 3485 N. Clark, (773) 755-3980; Spot 6, 3343 N. Clark, (773) 338-0185; Moxie, 3517 N. Clark, (773) 935-6694)

Date Seven:
Instead of going for drinks, grab dessert post-movie to put a sweet spin on your latest date. Try Wicker Park’s Sweet Thang for a wide variety of pastries, croissants, sandwiches, and American and French delicacies. Share the turtle cheesecake or the Swiss apple tarts.

Another option, Vanille Patisserie in Lincoln Park, closes earlier, but still works for a pre-movie treat—the Webster Place theaters are just down the street. The intricate sugary treats and award-winning pastry chefs will sweeten the deal before you head to the show.

Also, Sweet Mandy B’s has earned a steady following in the past year. Its sunny pastel décor, soda-shop ambience and yummy, whimsical desserts like peanut-butter-and-jelly cake make dessert even more deliciously indulgent than usual.

(Sweet Thang, 1921 W. North, (773) 722-4166; Vanille Patisserie, 2229 N. Clybourn, (773) 868-4575; Sweet Mandy B’s, 1208 W. Webster, (773) 244-1174)

Date Eight:
This time around your friends are asking about her—if they haven’t already met her. The perma-grin on your face refuses to wane. You two are an item, and let’s face it—things are getting serious. Pull out all the stops, get glammed up, and take her to Sushisamba Rio. It’s arguably the most talked-about restaurant opening in Chicago this year. The New York export serves up Latin beats, festive, sexy décor, and a full menu of South-American/Japanese fusion specialties. Share the rainbow roll or a sampling from the raw bar like the Amazon combination platter, and toast your budding romance with one of the signature cocktails from the caipirinha bar.

(Sushisamba Rio, 504 N. Wells, (312) 595-2300)