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The Drake
The Drake still exists, I swear. Though the once-great boutique beacon on West Queen West has lost some nightlife sheen in the last few years, the kitchen thankfully still retains its high-quality contempo fare with an Asian flare and an internal rhyme. Since its reconfiguration, the Drake has taken special events seriously. Whether it's a TIFF soirée, Pride bash, or New Year's party, celebrations never fail to impress. Valentine's Day will be no different. Trade in tablecloths and heart-shaped scrawls for inkblots and a laid-back though refined lounge. As a bonus, if you're a Stober-era local you'll have an easy stroll home. 1150 Queen Street West, 416-531-5042
Fare Bistro
As Leslieville's youth movement gains steam, the area continues to up its under-the-radar cachet. By next year everyone should know about the Queen East stretch, but now its emergence is nascent enough to lend it a subtle coolness. Thus, taking your Valentine's Day date east of the river will score you cool-kid points aplenty. Chef Brad Clark's Fare Bistro has helped lure foodies from far a field. The verdict so far? A bistro, yes, but not another pompous French operation: this is a Leslieville space. The result is an intimate room that seems much larger than it is. Whimsy continues in the kitchen. Clark has created a menu based on fresh ingredients and the intelligent use of herbs where the Le Select training really shows. 1097 Queen East, 416-645-0914
The Fifth Social Club
Swanker than cinnamon hearts, the Fifth has thrown off its pompous past but retained its shimmer. The Fifth's famous chef-delivered cuisine and ambient music will set the tone for sweaty suit romance. The Fifth is a package deal; people splurge here for the whole fantasy, getting the luxurious refinement they can’t get at home: swank upholstery, china, and silver, perfect lighting and unobtrusive velvet-glove service. Young risers, slicked briefcasers and slow walking fast talkers love this place, and so will most love martyr celebrators. 225 Richmond Street, 416 979 3000
George
Executive Chef Lorenzo Loseto holds court at George, dolling out stunning fare, from small-bite to big portion, so feel free to share or covet, depending on the nature of your relationship. Palate pleasing and alluring, George has all the flare of the bigger names, but for slightly less cost. Though dinner may not prove Sneaky-Dees cheap, it will keep you near the black, furnishing your with a post-dinner budget; though, like prom night, your Valentine's Evening plans should already be cemented. 111 Queen Street East, 416-863-6006