Interactive Winter Date Ideas

Toronto young professionals know how difficult dating is in this city. With busy social calendars, careers, and everything in between, young professionals don’t have time to fall in love the old-fashioned way. Gone are the days of getting to know someone naturally through facilitators like fun summer jobs, school and even friends, as they gradually begin to couple off, leaving their single friends to fend for themselves. Nothing seems organic about dating anymore. Typical scenario: you meet someone out, either at an after work bar, industry event or Saturday night hotspot, exchange numbers, then after a few often generic text messages agree on a time that works with both of your busy YP schedules. Then you pick a restaurant.

For many young professionals, a date is eerily reminiscent of a job interview. You return home with most of the basics answered; you know where one another is from, where they went to university, their career and personal goals and who your mutual friends are. You could probably have found that all out on Facebook or LinkedIn. What about the important things, like what makes them laugh, how they handle a challenge or how easily the two of you naturally interact? The best dates are those that facilitate interaction and bring out one another’s true character and raw personality, free from the constraints of awkward across-the-table dialogue in the eye line of others at a crowded restaurant. We know this is more of a challenge in the seemingly desolate winter months, but we have compiled some of the best winter date ideas for winter 2012 with varying interests and budgets in mind.

We are usually opposed to the idea of seeing a film, ballet or opera on a first date. Chances are you have barely had a chance to talk before you are left sitting in silence, staring straight ahead with a stranger for at least two hours of your life. How awkward. Live comedy, however, offers entertainment with more room for interaction between sets, booze and icebreaking humour. Either check out Yuk Yuks, the Second City Mainstage or Absolute Comedy for the uptown dwellers. Whatever you do, make sure that you don’t sit near the front – the last thing you need is to be called out for your hairstyle, clothing or laugh by the comedian on stage in front of your date. We’ve seen it happen. 

Anything that facilitates a friendly competition is always a good option. Bowl without compromising your style at The Ballroom or challenge your date to a round of ping-pong over Coronas at Spin. Of course, there is always paintball, but you may want to check with the lady first – returning home dotted with welts may be a total buzz kill for her.

Wine tasting is always a good option, especially if it is paired with a sexy food like chocolate. This winter, the Wineries of Niagara-on-the-Lake are offering a wine and chocolate tour for the winter months. At each stop of the 28 wineries, a different VQA wine is paired with a decadent chocolate. Afterward, check out one of the cute little restaurants on Picton Street to refuel for the drive home.

Revisit your youth with a skate date at one of the city’s famous ice rinks, like Nathan Phillip’s Square or Harbourfront’s Natrel rink. Grab a warm drink after at a local coffee hub or a nice glass of red wine at one of the many surrounding pubs. If you rent skates, be sure to bring an extra change of socks (and remind your date to do the same) so you don’t get the remnants of thousands of other feet in your own shoes. That’s not sexy.  

If it happens to be one of those inhumanely cold Canadian days, take the skating idea indoors at Scooter’s Roller Rink in Mississauga. Yes, cheesy, but come on, haven’t you always wanted to go to one of those? To stay away from the chaos of countless hyper-active children on wheels, make sure to go on a Thursday or Sunday for the adult-only skate from 8pm-11pm. Again, remember the socks!

Return to the simple pleasures with a good old-fashioned board game. A good option for the YP on a budget, Bloor Street’s Snakes and Lattes offers 1,500 board games, caffeine and a liquor license. This gives a whole new meaning to “going for coffee.” Isn’t that how our parents fell in love, over board games? That’s what they told us…

To get your adrenaline pumping, try indoor rock climbing at Joe Rockhead’s. You will get to see how the other reacts in a situation of challenge, focus and physical endurance.  It’s also a good excuse for the ladies to wear yoga pants and a ponytail, a welcomed alternative to spending hours fussing over that first-date outfit.

Unleash your inner child at the Ontario Science Centre. Unlike a gallery or museum, which may make for an awkward interaction and somewhat forced trying-to-prove-something intellectualism, the Ontario Science Centre facilitates interaction and play. We’ve taken even the most rigid YP there on a date and had a blast, crazy static hair and all.

If you are going to go to a restaurant, try something with an interactive or unusual twist like O Noir, where you dine entirely in the dark, stimulating your senses and facilitating reliance on conversation.  Devices like cell phones are not allowed during the experience, so you can be sure your date receives your total attention, even if you can’t see each other. Another bonus? They won’t be able to see your reaction if he or she says something stupid or awkward. 

For the ambitious type, why not drive to Collingwood for a day on the slopes? Sure, it’s a daylong commitment but you can chat in the relaxed environment of the car on the way there, get a good workout, and actually get some use from the skis you bought last year. Beginner skiers, this is not recommended unless your date is an ex-pro skier and is taking you there specifically to provide instructions. If the day of skiing goes well, then there’s always the option of getting a hotel and making a weekend out of it. Ok, it may be a little soon, but if you are spending 12 hours together, that’s the equivalent of waiting four three-hour dates until your first sleepover, after all.

Not all interactive date ideas are good ones, though. Things to stay away from include salsa dancing, karaoke and clubbing.  Trust us, we speak from experience.