Feels like the first time

FOUR SCORE Couples get close at new spot A Mano.

No matter how unmemorable your Valentine’s Days have been in the past, there’s one thing you and your date will always remember. It’s not the box of candy, not the cubic zirconia—it’s not even the way you butchered “I Want to Know What Love Is” during karaoke. It’s the meal.

So if you must use the same hokey lines as last year, fine. Go ahead. But out of decency to yourself and your date, try one of these ten places where you couldn’t possibly have spent Valentine’s Day before—because they weren’t even open.

ITINERARY 1: Bad Behavior in the South Loop

There’s no way to know exactly what Al Capone would have done on Valentine’s Day. But we’re pretty sure he wasn’t drinking pink cocktails with names like “Cupid’s Arrow.” Nevertheless, if you’re at Room 21 (2110 S Wabash Ave, 312-328-1198), which sits on the former site of one of Capone’s old haunts, you can make your date believe that you’re somewhat of a bad boy (because who doesn’t like a bad boy?). Just forgo the special cocktails and go straight for the black-and-blue steak and the seared diver scallops with parsnip puree. As much as you may want oysters and caviar, don’t order them—they are distastefully labeled on the menu as “A Sure Thing,” and ordering them will ensure your date is not.

After that, walk one block over to State Street to Reggie’s Music Joint (2105 S State St, 312-949-0125). Your date might have been expecting Champagne and strawberries at a wine bar, but guess what? You’re going to go the beers-and-band route instead. And you’re both going to like it, because that night you’ll see Hostage Juliet, a band that sounds, appropriately enough, a bit like My Bloody Valentine.

ITINERARY 2: Roses in River North

Take note: The roses that A Mano (335 N Dearborn St, 312-629-3500) will put on your table on Valentine’s Day are only optional in theory. In practice, you’ll want to order at least a dozen ($58, compared to $30 for the half dozen), which will be placed on your table before you arrive. The idea here is to have the flowers overtake the table, so much so that your date will have to move them out of the way just to get a forkful of Florentine steak, housemade pasta or the special “Italy is for Lovers” dessert (cannoli, gelato, chocolate cookies, blood-orange crostata). Because if you neglect to buy roses altogether? You’ll have to explain why your table is the only one without them.

But don’t worry—those are the only flowers you’ll have to buy all night. At nearby NV Penthouse Lounge’s (116 W Hubbard St, 312-329-9960) Lust v. Love event, every woman will get a rose upon entering. There’s a $20 cover, but don’t sweat that: Just e-mail info@nvpenthouselounge.com to get on the early guest list and you’ll enter for free. (Tell your date you know somebody.)

ITINERARY 3: Luxury in the Loop

The sad fact is that it’s terribly difficult to do something special for Valentine’s Day; take a date to dinner and all you’ll see are other people doing the exact same thing. But for originality points, nothing will smack of exclusivity more than dinner in The Library. What’s the Library? Exactly. It’s a private, members-only club on the 40th floor of 190 South LaSalle Street that you’d never have access to…until tonight. The Shikami brothers (who took control of the Library’s food and drink program when they opened Shikago on the building’s first floor) will open the room for a five-course degustation to the tune of a live harpist. ($140 per person; call Shikago at 312-781-7300 for reservations.)

The only problem with a dinner like that? It’s hard to compete with the view. So your next stop should be La Pomme Rouge (108 W Kinzie St, 312-245-9555), where you’ll sip Champagne cocktails among folds of lush fabric, and while none of the Chicago skyline will be in sight, take heart: This place attracts plenty of eye candy.

ITINERARY 4: Going Both Ways in Bucktown

There’ll be no special menu at Takashi (1952 N Damen Ave, 773-772-6170), and for your date, who likely has spent too many Valentine’s Days spooning “aphrodisiacal” soup out of heart-shaped bowls, this could be a good thing. And even without the kitschy V-Day promotions, there still will be plenty of romance: Chef Yagihashi’s food (pork belly with steamed buns, seared hamachi) has a pretty good track record when it comes to making people swoon.

After dinner’s over, that’s when you bring on the kitsch. At Plan B Bar + Kitchen (1635 N Milwaukee Ave, 773-252-2680), it’ll be ’80s night, with peanut-butter cup fondue as well as marshmallows, Rice Krispies treats and pound cake for dipping; ’80s love songs on the speakers; and Say Anything on the TVs. (And here’s a little tip: If you get a weepy embrace during the “In Your Eyes” scene, the date is going well.)

ITINERARY 5: Lovesick (or Sick of Love) in Logan Square

The date who is anti–Valentine’s Day can be hard to please, especially on, um, Valentine’s Day. But if you can convince the curmudgeon to go out anyway, head to Logan Square. Not only is it the city’s center of hipster indifference, it also has a surplus of businesses that don’t care what holiday it is: They just want to feed you and get you drunk. For that first goal, try Gloria’s Café (3300 W Fullerton Ave, 773-342-1050), where you’ll share the bandeja paisa (country plate), feeding each other skirt steak, housemade sausage links, corn cake and crispy chicharrons. (Seriously. Nothing says “I really like you” like a hand-feeding of fried pig skin.)

After that you may be so full you can hardly walk (what a sexy way to feel on VDay, right?). So make it easy for yourself and go no further than across the street to The Burlington (3425 W Fullerton Ave, 773-384-3243). It’s dark in there (a good way to hide your protruding stomach). And mellow. And you can drink beer that is technically illegal (just point to the unmarked tap). But if that’s the sort of thing that gets you and your date into the Valentine’s Day mood, try to save the makeout session for home…the crowd in here is just so over PDA.