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Plan Carefully for the perfect ‘holi-date’


La Tavernita

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Updated: December 7, 2012 6:51PM

Planning a date can be tough. But during the holidays, it’s an adventure. After all, the holidays serve as somewhat of a “make it or break it” time in the dating world.

Let’s just say… you better not screw this up!

Take a deep breath. Luckily for you, there are countless options in Chicago this time of the year that can’t help but contribute to a memorable evening. Check out some of our very favorite themed date nights, and start making some reservations. And whatever you do, take complete credit for a job well done…we won’t tell.


Have a hot date planned? Break the ice without breaking the bank with enjoying some oysters at places such as Tavernita. Oysters are now only $1 from 5-7 p.m. every day. And heck, oysters are among the most commonly known edible aphrodisiac. Warm up the cockles of your heart with a nightcap at Andersonville’s Simon’s Tavern, known to have some of the best glogg in the city.

Tavernita, 151 W. Erie, 312-274-1111; Simon’s Tavern, 5210 N. Clark, (773) 878-0894.


Sure, you love to shop … but on a date? Give it a chance. Throughout the holiday season, Chicago French Market features the Marche de Noel market with many vendors selling unique gifts perfect for the holidays. Running through Christmas Eve, Christkindlmarket is also becoming a favorite for the lovebirds, offering a slew of traditional German wares and delicacies.

Chicago French Market, 131 N. Clinton, (312) 575-0306,; Christkindlmarket, Daley Plaza, 312-494-2175,


Are you in love with a foodie? Check out Frontier as they host their first exclusive “So You Think You’re a Foodie” chef’s table dinner on Dec. 19 at 8 p.m. For $60 per person, guests (make a reservation!) are invited to indulge in a mystery five-course tasting menu showcasing unique and delectable fare. Another foodie gem is Benny’s Chop House, home to an incredible gingerbread village designed and constructed by pastry chef Aaron Lindgren.

Frontier, 1072 N. Milwaukee, (773) 772-4322, Benny’s Chop House, 444 N. Wabash, (312) 626-2444,


What are the holidays without a trip to the theater? (And heck, where else than a dark theatre can you do the “yawn … arm around her” trick?) Lookingglass Theatre Company is featuring the Tony Award-winning “Metamorphoses,” Mary Zimmerman’s critically acclaimed drama. Want laughter instead? Check out the “Book of Mormon” at Bank of America Theatre starting Tuesday.

Lookingglass Theatre Company, 821 N. Michigan; 312-337-066, Bank of America Theatre, 18 W. Monroe, (877) 280-9582; www.


So, your budget might not allow the chance to sweep your love in your arms to an overseas paradise. Bistro Voltaire is the perfect romantic spot for those wanting a truly French experience without the expense of a plane ticket. Looking to add a little Hawaiian paradise to your snowy Chicago winter and open to taking a trip out to the suburbs? Stick with the tried and true Bob Chinn’s World Famous Mai Tai, made with premium real fruit juices and distilled dark rum crafted in the Hawaiian Islands. Throw on a grass skirt and you are set.

Bistro Voltaire, 226 W. Chicago, (312) 265-0911,; Bob Chinn’s Crab House, 393 S. Milwaukee Ave. Wheeling, (847) 520-3633,


Sure, you act as if you are a loving couple blessed to have one another on your joint Facebook page. But bring out a deck of cards, and all bets are off. Looking to get competitive on your date? Check out Bull & Bear, who offers trivia on Tuesday nights. Or get down with your bad self with some good ole board games at Blue Frog Bar & Grill.

Bull & Bear, 431 N. Wells, (312) 527-5973; Blue Frog Bar and Grill, 676 N. LaSalle, (312) 943-8900;


Sweating on a date is never a good sign, unless you are trying out some of these fun ideas! Head over to Flywheel Sports and check out an indoor cycling experience like no other. Not a big fan of sweat? Try a low-key game of bowling at Lucky Strike!

Flywheel Sports, 710 N. State, (312) 624-8485,; Lucky Strike, 322 E. Illinois, (312) 245-8331,


A pub crawl always starts out with the best of intentions ... it’s not till you are sitting on a curb at 2 a.m. that things start getting a little fuzzy. Celebrate the holidays — Wrigleyville-style — at TBOX 2012, an annual event celebrating the “Twelve Bars of Christmas.” TBOX 2012, Wrigleyville, (773)478-3378,


Whether your date likes fashion or you simply like looking at good-looking people, look no further than the Chicago Couture Fashion Week Fall/Winter Show on Sunday. Support young artists and designers at this unique fashion show, which also raises awareness for youth experiencing violence in Chicago. Not sure what couture even means? Join the crowd at Howl at the Moon on Dec. 14 and 21 for their annual ugly holiday sweater party!

Chicago Hilton and Towers, 720 S. Michigan, (312) 459-8511; Howl at the Moon, 26 W. Hubbard, (312) 863-7427;


Put you behind a bar — would you know what to do? Learn how to make a stiff one at Cityscape Bar on Dec. 13 as part of their ongoing Mixology 101 demonstration series. Or head on over to The Chopping Block in Lincoln Square for an “Eat, Drink and Be Merry” hands-on class on Dec. 14.

Cityscape Bar, Holiday Inn Mart Plaza, 350 W. Mart Center Drive, (312) 836-5000; The Chopping Block, 4747 N. Lincoln, (773) 472-6700,

Tricia Despres is a local free-lance writer.

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