As discussed last week, I believe there are 5 pieces to the perfect date. Those 5 pieces are shown in the image above. Understanding why those pieces are important is one thing; knowing where to find them in a big city like Toronto is another.

Junk Food

Sometimes, you just gotta cut loose and get high… sugar-high, that is. Usually when taste buds are satisfied and self-control is thrown under the 18-wheeler, moods lift and people talk. It has actually been proven psychologically that when self-control is diminished, cognitive capacity frees up. And just think about your own experiences, when was the last time you heard someone over the age of 10 being an asshole while they ate ice cream? When have you seen someone get awkward and shady while scarfing a poutine? I’ve always said: the food court at the CNE is the happiest, saddest place in the world.

So every once in a while jack up your spirits, toe-punt your immune system and dive into some juicy conversation while splurging on some tasty treats.

Sweet Olenka’s — 2790 Lakeshore Blvd West
Move over Dutch Dreams and pervy ice cream trucks outside public schools. Recently voted the #1 Ice Cream in the city through an online poll, Olenka’s certainly seems like it’s worth the drive to Etobicoke. But it’s not just ice cream; they also have over 20 different hand-crafted chocolate bars—including the pseudo-healthy “Super Anti-Oxidant Blueberry” bar. They also offer an array of cakes, and for those of you going on a date in the 1920s, chocolate truffles.

Caplansky’s Deli — 356 College Street West
Their smoked meat is fantastic, but what you really want to grab here is the poutine. They have some of the best fries in town (at $4) but upgrade to the $6 poutine and you might become religious…Jewish, to be precise. The gravy is actually made from smoked meat and mixed with cheese curds. It’s no Stairmaster, but I wouldn’t be surprised if it got both of you sweating.

Food Dudes Food Truck — Check Twitter
There aren’t too many amazing food truck experiences to be had in Toronto, but The Food Dudes is as good as you’ll find anywhere. Specifically in the junk food department, their Nutella Bomb—banana bread, smothered in Nutella, topped with banana slices, then deep-fried and bathed in whipped crème. Ya. It’s unreal. The only question is, where is the food truck? Better follow them on Twitter.

Cheesewerks — 56 Bathurst Street
As much as it pains me to condone the application of “Artisan” to the world of grilled cheese sandwiches, this place has some delicious food. Ranging from $7.50 to $10, they offer a concise but well-diversified menu of city-inspired options. The Beijing is made with asiago, BBQ pork and hoisin while the New York goes deli-style with swiss, pastrami and pickled cabbage. The bread also ranges from peppercorn sourdough to walnut-raisin. Either way, you can’t go wrong with cheese and bread. Unless you’re lactose-intolerant. Then maybe just have one of their organic gingersnap cookies.

A Solid Laugh

Rashes and hypoglycemia aside, laughter truly is the best medicine. It’s also one of the best ways to ensure a healthy, memorable date. Endless psychology studies have shown that forcing people to smile during cognitive exercises leads to a more relaxed approach with a greater sense of confidence. If people are walking away from a date with a sprained jaw and an ab workout, someone did something right. Wait…what are we….oh, right. Comedy.

While humor tastes will vary, it’s at least helpful to figure out what tickles everyone’s funnybone. Whether it’s stand-up or skit comedy, loosen up, unfurrow the brows and try one of these great spots for making your date a laughing matter.

Comedy Bar — 945 Bloor Street West (Downstairs)
Consistently the funniest joint in town. I highly recommend the Catch 23 show which runs almost every Friday. Admission is only $10 per person and it’s a solid couple of hours of top-shelf improv with different players every time. Warning: You might pee yourself…and your date might be into that.

Bad Dog Comedy Theater — 875 Bloor Street West (Upstairs)
Somewhat of an extension of Comedy Bar (they’re about a block away from each other and they seem to swap players), this spot just opened up about a month ago in the old Baltic Avenue space. It’s a very unique layout in a very intimate room so the experience can start off a little awkwardly but the talent will make sure everyone gets in a groove. Most of the good shows are on Saturday night and are also only $10. If you want an improv experience on the unique side, this is your spot.

Second City — 51 Mercer Street
This company is no secret and despite their designated profession, it’s also no joke. They consistently kill it with their revue using some of the wittiest, most original content you’ll find on the skit comedy circuit. Depending on the evening, the shows are between $14 and $34 and you can also get a dinner and show package for around $60, which includes a half-decent meal at the adjoined Wayne Gretzky’s. It’s also worth making this a regular event as they switch up the revue every few months. After the show, hit the rooftop patio above at Oasis. Or, if you’re feeling like an asshole, take your date to one of the several clubs on Mercer.

Absolute Comedy — 2335 Yonge Street
For good stand-up comedy, it’s worth making the trek to mid-town. With a great room and a solid roster of headliners, this club will rarely disappoint. Amateur night on Wednesdays is only $6 but it’s probably best to take a date on Thursday ($10) or Fri/Sat ($15). They do offer a dinner and show special for $23-$27 but at this spot, I’d probably leave the jokes to the comics and not the cooks.
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Benjamin Mann is Toronto’s Standard dating columnist. Follow him on Twitter.

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