3 Not-So-Basic Toronto Date Night Ideas

If you have managed to find someone worth your time and actually think this might possibly maybe be the one, then you deserve to go on a date night that’s anything but basic. We have found cool twists on your typical traditional-style dates to really help you guys get to know each other on a more fun and intimate level or to spice things up for relationships that are already well under way. But these really are super awesome so make sure you save these ideas for someone really special!

Instead of Drinks, Try Paint Nite

Cost: $$

Going out for a drink is great because, well, wine. Wine is great. And you know what else is great? Painting!

Paint Nite events happen all over the city all the time at all kinds of local bars. Tickets run for about $50, which gets you in and painting. They provide you with all the tools you need to paint a pretty picture AND you can drink while doing it! If you have little or no art skills, have no fear”they guide you through the process step-by-step, kind of like a paint-by-numbers deal but a little more challenging.

You can choose your Paint Nite based on date, artist, location, or painting, but realistically if you don’t like the painting, you are more than welcome to paint whatever you want instead. It’s all you so feel free to go crazy on that canvas.

You and your date can relax and bond over drinks and paint, all while sharing a cool and creative experience that will allow for a deeper kind of connection. The best part? Both you and your date will have a cute keepsake to remember your awesome date night.

Tip: Arrive early if you want to grab a bite to eat. You can eat while you’re painting but there is a chance that some paint might be flung into your food during a moment of inspiration. Also, try to keep your drink and your paintbrush cup in different places, as it is all too easy to accidentally clean your brush in your drink or take a swig of gross paint water.

Instead of Movies, Try an Outdoor Movie

Cost: $

You could sit in a movie theatre and catch the latest flick, or you could sit in a lawn chair or on a blanket on the grass (which we recommend for your date cause it’s way snugglier) and catch all kinds of oldies but goodies.

Various outdoor movie screenings take place throughout the city while the weather is still warm, including the Christie Pits Film Festival at Christie Pits Park, City Cinema at Yonge-Dundas Square, Harbourfront Free Flicks at the Harbourfront Centre, and TIFF in the Park at David Pecault Square. And in honour of their 40th anniversary, this year TIFF is also expanding to other locations for another movie event called TIFF in Your Park, which is screening movies until late September.

Generally, these events are either free or PWYC (pay what you can) so they are especially good if you’re strapped for cash. There are also food vendors on site but, unlike movie theatres, you’re totally allowed to bring your own snacks.

Watching a movie in a park or other outdoor location is great because not only do you get to enjoy the sunset and scenery, but you also can get a lot cozier than you would in typical movie theatre seating (that damn arm rest always gets in the way!). These kinds of things always have great vibes and really, nothing is better than snuggling up to your sweetie while watching a screening under the stars.

Tip: Bring lots of blankets because being cold sucks and if you will be sitting on the grass, pillows are good so you can lie down but still prop yourself up comfortably. Also, wine in a thermos because, again, wine.

Instead of Dinner, Try Escape the City

Cost: $$$

Work up your appetite on this outbound adventure that rewards you with a picnic dinner provided by a team of professional gourmet chefs. The Culinary Adventure Co. brings you an opportunity to Escape the City by embarking on a canoe trip right here in the city. You will love getting your Canadian on for this romantic stay-cation.

It starts at the Harbourfront where you and your boo will jump into a heritage freighter canoe and begin paddling out to the Toronto Islands. Don’t worry, you will have a professional canoe guide with you to keep you on track and also give you some background history about the area. You’ll explore a bird sanctuary and glide past the sailboats at the yacht clubs, while planes take off and land from Billy Bishop airport overhead.

Once you reach shore, you get to enjoy a gourmet dinner made from local Ontario products while watching the sun set over the water. Relax, digest, and take it all in before paddling back to the city. If you have never been to the Islands, you will experience a view of the amazing city skyline that will give you a newfound appreciation for Toronto.

Tip: Bring a camera and take LOTS of pictures!

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