Your choice of spot for a first date is crucial. It needs to hint at your winning personality and good taste while still exhibiting a sense of restraint. Being able to hear each other's attempts at conversation is absolutely necessary, so give a hard pass to any place that blares the Our Fried Chicken Is Gangster Spotify playlist of 90s hip-hop or attracts crowds of people screaming "WOOO!" between $4 shots.
I also advise against bringing first dates to your local, because you know the bartenders will just judge you silently.
My picks: Nuit Social (1168 Queen West, 647-350-6848), where you can nibble on charcuterie plates in the glow of the stained-glass bar, or take advantage of the $65 prix fixe special at Parkdale's trendy nautical Commodore (1265 Queen West, 416-537-1265).
This might run counter to traditional second-date wisdom, but I submit that you'll want to go even more low-key if your second meeting falls on Valentine's Day. (You don't want this person thinking you've already made the decision to spouse them. Play it cool!)
Lucky Red (318 Spadina, 416-792-8628) has a vibe that's boisterous and relaxed, food that isn't fussy and reasonable prices, but the red walls and spicy-sweet cocktails add understated romance.
Or go to Bar Fancy (1070 Queen West, 416-546-1416) and squint at each other in the dim lighting, brushing hands as you both reach for another piece of fried chicken.
And we all know what happens on the third date. (Disclaimer: this is a hoary old stereotype, and you don't have to do anything you don't want to do on the third date, or at any other time.)
If you're looking to set the mood, Anthony Rose's Bar Begonia (252 Dupont, 647-352-3337) and Jen Agg's Rhum Corner (926 Dundas West, 647-346-9356) both bring the low lighting, sexy cocktails, snacks you can slowly feed one another - if you can do that without giggling - and murals featuring a lot of naked people.
You're on top of the world! You wanna show off your new piece of arm candy! What better place to do that than the oh-so-celebrated Alo (163 Spadina, 416-260-2222), where you really will be on top of the world (or a third-floor dining room overlooking Queen West, to be exact).
Drop half a paycheque on an assortment of Patrick Kriss's perfectly calibrated small plates, then hit the clubs if you haven't yet made out in enough public places that evening. Might we suggest pulling up a sofa at Apt. 200 (1034 Queen West, 416-357-1299)?
The Captain's Boil
Why get all gussied up for Valentine's Day when you have this snuggly, fleece-lined relationship cocoon where you can stagnate forever?
To step up your game for the sake of a special occasion, skip your usual janky delivery provider (my guess is it starts with "Pizza" and ends with "Pizza") and call up Maker (59 Cameron, 416-782-2000). My pick is Frank's Best, a sophisticated mix of caramelized onions, honey, goat cheese and rosemary on a sesame crust.
Or put on pants and head down to The Captain's Boil (476 Yonge, 647-748-2886), where you can slurp down boil-in-a-bag crab legs and shrimp, because you guys have given up on looking sexy in front of one another anyway.
TRYING TO KEEP THE FLAME ALIVE
Dealing with relationship problems? You should probably just throw some money at 'em. Canoe, Café Boulud, Nota Bene and Momofuku are all classic big-date splurges - but they're probably all booked up by now. (Sorry.)
Why not dine on sashimi (and slowly realize you have nothing more to talk about) surrounded by the young-money crowd in the icily contemporary dining room at Kasa Moto (115 Yorkville, 647-348-7000)?
Or hit Boralia (59 Ossington, 647-351-5100) for their $65 prix fixe. The sense of adventurousness that comes from dining on bison bresaola, pigeon and whelk might help convince your partner to try something new in the bedroom, but the dinner will probably be far less awkward and involve fewer novelty pairs of fuzzy handcuffs.
GOING DOWN IN SMOKE AND FLAMES
Here we set the stage for your relationship's last stand. Parts & Labour (1566 Queen West, 416-588-7750) is nice and loud, so nobody will hear you hissing back and forth about that disastrous weekend with your significant other's parents.
It would be awfully satisfying to flip a table in the fussy room at Cluny (35 Tank House, 416-203-2632). Plus, the Distillery location means your angry stomp away from the restaurant will be extra dramatic, and you can glare at the happy couples looking on.
If you want to throw the fanciest possible cocktail in someone's face while screaming, "How dare you," I'd recommend BarChef (472 Queen West, 416-868-4800).
Get more Valentine's Day ideas here!