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The five pieces that make up the perfect Toronto date—part one
"We tend to ask the wrong questions when it comes to a planning a great date."

Whether it’s the Feeler First, the Steamy Second or the Old Hat Hundredth, dates are important events in a relationship. While I have met couples that look forward to gardening and reading together—also known as, “doing nothing”—most people invest in relationships to have someone not only complement but enhance their sometimes monotonous journey through life. The right person can make any experience more interesting but architecting the right context can take things from interesting to awesome.

As in most areas of life, though, we tend to ask the wrong questions when it comes to a planning a great date.

“Where should we go?”

“What should we do?”

The first psychological step is usually an exercise in retrieving easily accessible names of places that offer a craved food or drink—like pizza or Jägerbombs—or that facilitate a craved activity—like playing tennis or heckling tourists. Undoubtedly, if you simply satisfy a craving, further secure yourself as the significant other or fend off a stale evening of sweatpants and shows starring Julianna Margulies, you’ll have accomplished something positive. However, there’s more that can and should be accomplished with a date, especially in the early stages.

The real question to ask is, “What does this date need to help us move things in the right direction?” And don’t just say “booze”. Technically you’re right, but you’re also missing the point.

With a date, you are ideally exploring the corners of someone’s character and personality. You are encouraging an intimate exchange of beliefs and assessing the nuances of your compatibility. You are building unique, fond memories and inspiring laughter, excitement and healthy frivolity. It’s about discovery, experience, memory and levity. It’s not just about killing time and cultivating commitment to establish partnership and entitlement to sex on a Wednesday morning—though don’t get me wrong, that’s pretty important too.

So what kinds of things would a date have to maximize the odds of achieving such romantic goals? Well, I’m glad I asked.

Below is what I consider to be “The Five Pieces of the Perfect Date”.

It is possible that you hit all of these things in one place with one activity, or at least get some serious overlap. And that’s cool. But the perfect date would snap in all the pieces independently through an itinerary bursting with entertainment and shenanigans.

The only exception is the “Artifact”, a physical token to remind people of a good time and to associate the positive sentiment with the person who made it happen. This element is important but it’s not necessarily its own distinct path. Sure, you could go out of your way to buy a whacky post card or steal a visor from a McDonald’s employee. But what’s important is that somewhere along the way you find something more interesting than a ticket stub with which someone can walk away and reminisce. You might think it’s cheesy, but trust me, it’s worth it—especially if it’s an early-stage date and you two end up doing some crazy shit like getting married.

Ideally, you have an afternoon and an evening to pull this all off, but that’s not necessary if you plan adequately and you don’t have a 13 year old’s curfew.

Nailing all 5 pieces would be a grand slam. But if you can’t do all 5, always swing for at least 2; that’ll make sure you’re moving the runners in the right direction. And if you don’t like baseball metaphors, we clearly can’t be friends.

Now, with the right framework in place, we can ask, “Where?” Where can you go in your home city to find the 5 pieces of the Perfect Date?

Personal taste plays a big role in this, but if you live in Toronto, here are some ideas to get you going:

A Competition

Annoying people are often most annoying when provided a direct, sustained opportunity for some kind of victory; or more importantly, some kind of loss. A friendly challenge is always a great way to gauge someone’s ability to have fun in the face of negligible ego stakes. Do they keep up or do they surpass? Do they show off or do they engage? Do they compliment or do they taunt? Do they talk or do they whine?

It’s also great to establish some sort of “hobby” that encourages quality time, spikes a bit of adrenalin and generates vivid, entertaining memories. Playful rivalries are great for humor, attraction, bonding and story-telling. So next time you’re looking to get face-to-face with that special someone, consider going head-to-head with them at one of these places:

On Cue Bar & Billiards — 349 Jane Street
With its second floor location and its dusty film noir lighting it has the classic hints of a seedy pool hall, but between the good music, the lively patrons and the friendly ownership, it’s far from a dive. It’s also priced like it was in a Humphrey Bogart movie: $5 per person for all-you-can-play pool in the evenings.

B.A.T.L. Axe Throwing —213 Sterling Rd or 33 Villiers Street
If you haven’t had five drinks and thrown an axe at a slab of wood, you haven’t lived. You can book individual visits or you can join their league that runs Sunday to Wednesday inclusive. The pricing is reasonable for the amount you get to play, the instructors are great and there’s nothing sexier than watching someone re-enact a Mel Gibson scene without the racial slurs. It’s also a lot harder than you’d think. The axe-throwing, not Mel Gibson.

Snakes & Lagers — 488 College Street West
It’s a cool bar and it has just about every board game ever invented—over 250 of them. Can you say win-win? There have somewhere around 20 beers on tap (about $7 a pint), a solid cocktail list and some pretty tasty food. Go one-on-one for a pint and a quick game of Uno or grab a snack and learn some lessons about the game of Life. This place will get the healthy competition and the conversation flowing. Loser buys.

Frolf (Frisbee Golf) – Ward’s Island / Toronto Island
George Castanza was onto something. Mini-putt is cliché, Strip Mini-put is illegal and chances are, you’ve never tried Frolf; at least not with an official course and a scorecard. Grab $7 for the ferry, a picnic basket full of goodies, a Frisbee, a pen and a notepad. It’s easy, it’s fun and it’s a total nightmare finding your way around the course. You can find a map of the course here but it might be more interesting to wing it; while you’re in game mode you might as well see who wins the Chris Columbus Navigation Award.

A Weird Experience

Nothing opens the door to memorable conversation like an off-the-wall experience. It doesn’t have to be bat-shit crazy; just enough off the beaten path that people are nudged towards the edges of their comfort zone, providing people an opportunity to warm up or clam up. If you’re someone who loves new things and goes with the flow, you’ll need to know if your partner can keep up. If you like living in a bubble, you’ll need to know if your partner is going to pop it.

Also, if it’s just weird enough, and you two are on the same page, bonding doesn’t get much better than cracking jokes about something you both find absurd. Relationships should be stable but they shouldn’t necessarily be “normal”. Go make it a bit weird.

Toronto Love Psychic Center — 65 Elm Street
For the record, I think these people are all loons, scam artists or both. That being said, many are lovely characters that have the power to magically transform bullshit into stimulating dinner conversation. Specializing in love and relationships, Vanessa will offer you and your date pertinent, novel insights, if not entertaining ones. For $40 to $100, you get a game of creepy blackjack with oversized playing cards in a room brimming with supernatural energy. Due to limited online resources and an ambiguous voicemail greeting, I’m not 100% sure if Vanessa still runs this business. But I imagine if you wonder about it really hard, she’ll call you to book an appointment.

O.Noir Restaurant — 620 Church Street
By now, most Torontonians have heard of this restaurant. But I’m not sure enough of us have tried it. Eating in the dark is really quite an odd but highly stimulating experience. The dining room is literally pitch black and they even have blind servers. You are forced to use all your other senses and many people end up doing everything—and I mean everything—with their hands. And I guess maybe their feet a bit too…You can expect to spend about $30-65 a person, getting to the higher end if you get drinks. At this spot there’s plenty for you and a date to hear, taste and discuss. And, more importantly, you’ll never get caught for lobbing a shrimp into someone’s Prosecco.

The Hot Box Café — 204 Augusta Avenue (Kensington Market)
The slogan on their website is, “Serving Potheads Since Ah…I forget”. How great is that. I don’t smoke weed, nor do I particularly condone its use, but that doesn’t mean I can’t appreciate the extremities of its culture.  Walk through Roach-o-Rama and make your way to the back patio that “seats 40 happy stoners”. You can grab a coffee during the day or go after 7pm for their “Afterdark” program that includes “Stoned-Up Comedy” on Thursdays or “Reggae & Games” on Fridays. If you’re looking to get high, it’s BYOP, but as far as I’m concerned, you’ll get enough OMG without the THC.

Tune in next week when Ben concludes his look at what makes a perfect date in Toronto.

Update: part two can be found here.
Benjamin Mann is Toronto’s Standard dating columnist. Follow him on Twitter.

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