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Valentine's Day 2010: It's Complicated

View A Highly Situational Culinary Survival Guide in a larger map If I learned anything from a certain geriatric rom-com over winter break, it's that relationships start complicated and only get more so with age. Until you're sexting your ex (-wife!), you've got nothing on Alec and Meryl, but choosing where to make dinner reservations for Valentine's Day can get real hairy real quick. We're all different, and (let's hope) our dates are too, so treat the following restaurant recommendations not as blueprints for guaranteed romance but rather as situational sketches from which to make the night your own. If looking to elicit an "Oooh, you shouldn't have" from your fairy-tale princess, Upstairs on the Square is the girliest, ritziest and, yes, most expensive option in town. Provided your wallet can absorb the hit ($125/$185 prix fixe with champagne/wine pairing), this should be a no-brainer - nothing says Valentine's Day like hot pink walls, zebra-striped carpet and ribsteak for two. Fiscal conservatives (or those making reservations too late in the game) who still seek the unrivaled ambiance of the Upstairs compound can settle for brunch ($38), a choco-centric 3-tiered afternoon tea ($32) or dinner at the (only somewhat) more affordable Monday Club Room ($85/$135). If playing it safe with a newer flame, Temple Bar is the French vanilla of Cambridge restaurants. Casual but not careless, fancy but not gourmet, this Harvard Law School hangout is middle-of-the-road in more ways than one. Located on Mass. Ave. halfway between Harvard and Porter squares, "Temple" (as regulars say) offers a 3-course prix fixe ($49/$69 with wine pairing; limited prix fixe available Fri. & Sat. nights) that starts strong (fried oyster "billi-bi" soup) and ends stronger - handmade chocolates, candies and edible flowers, oh my! If aiming to please your foodie fiancé with great food sans the gimmicks, make yourself at home at Red House. The 4-course prix fixe ($50, beverages excluded) includes both a pasta and an entrée, so you'll leave every bit as stuffed as the lobster you just ate! Its dining room isn't the most intimate and its ambiance isn't the most romantic, but where else can you get grilled bison ribeye with sour cherry chipotle barbecue sauce this Valentine's Day? Just don't take an animal rights' activist here - the crustacean-heavy menu is sourced from a tank right inside the front door. Lobster fail! If hoping to earn indie cred with your too-cool-for-B-school date, hit up West Side Lounge for hip drinks, hipper music and a 3-course prix fixe for only $35. Expect womanly drinks (think cosmos, 'ritas and 'tinis) and manly rock (Deerhunter, Broken Social Scene and Built to Spill), both turned up to 11 with awesomeness. Alternatives include a brunch - complete with mimosa flight - and a Broken Hearts Bar for, well, not you and your squeeze! When you head to West Side, there's going to be good food and there's going to be loud music. When the DJ plays Postal Service, just don't ask "Is this the new Owl City?" If wanting to make a foreign friend (read: lover) feel more at home this Valentine's Day, Garden at the Cellar has a decidedly un-American vibe that's both relaxing and refreshing. A small restaurant with smaller tables (but not smaller portions!), Garden features a 3-course prix fixe ($50, beverage excluded) that sounds as simple (rack of lamb, lemon tart) as it does scrumptious (crispy pork belly and roasted sausage). Act now, though, because a 4.5-hour window + a mere 11 tables = oops, reservations are full! If you've yet to DTR (Define The Relationship, duh!) with your maybe-baby, beeline for the greasiest restaurant around (think Charlie's Kitchen, iHop or Pinocchio's and remain as ambiguous as humanly possible. That way, come February 15, if it turns out you and your at-least-somewhat significant other were in fact dating, then you did go on a dinner date, but if you weren't dating, then you merely broke bread together on any given Sunday ("Yesterday was Valentine's Day?...I totally didn't realize!") Genius, I know. If comfortable downing a pound of guacamole in front of your Valentine, you're probably happily married, and Olé is probably the place for you. This upscale Mexican grill offers an intimate back room and a bustling front room, both as colorful as they are fun. Resist the temptation to fill up on chips, salsa and guacamole (the latter two made tableside) - the 3-course prix fixe ($35/$40 with strawberry margarita) has more flavors (shrimp cocktail, tuna ceviche, chicken mole) than a Dr. Pepper. Tucked away in the oft-overlooked Inman Square, Olé's greatest asset is perhaps its location. Christina's (world's best ice cream) is right around the corner, whereas HBS isn't. The resulting walk home is both gratifying and grueling. Given the amount of calories you'll have consumed, that's likely for the best! If trying to fool your newfound love into thinking you know how to cook, take the T to Dave's Fresh Pasta in Davis Square. Expert employees will guide you through a gamut of flavored raviolis (pumpkin, artichoke, lobster, etc.) and other handmade pastas, then help you pair your noodle of choice with an accompanying sauce, bread and oil (all fresh and sold in-house). So long as you can boil water, you'll be serving up a gourmet dinner for two, and your Valentine will never know the difference! For meat lovers who want to add another course to the meal and another layer to this farce, pick up a cut of the finest protein in town (think Kobe Wagyu sirloins, wild boar bacon and whole rabbits) from Savenor's, Julia Child's long-time butcher/buddy. The only downside: future expectations. If courting a not-so-reformed chocoholic, let Finale be your finale this Valentine's Day. Both the 2-course ($55/couple) and 3-course ($70/couple) prix fixes end with the aptly named chocolate caramel tryst, a dessert for two that somehow combines molten chocolate cake, caramel sauce, milk chocolate caramel pastry, passion fruit gelée, praline crisp, chocolate covered marshmallows, dark chocolate bark, crystallized oranges, tart cherries, cocoa nib baklava, walnut fudge cake AND vanilla anglaise. You can, of course, sub tamer desserts for the tryst, but your date might just slap you silly! So much for that floral arrangement and bottle of champagne ($60 to $105 extra) you that you're single, best make other plans!

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