When a friend asked for advice as to where to propose to his girlfriend within the confines of Toronto, a brainstorm session ensued.
As it turns out, there are a ton of options (some admittedly cheesier than others) year-round when it comes to popping the question.
In no particular order, here are just 18 of them…
1. Underneath the Cherry Blossoms in High Park
Especially if you have a photographer hiding in the sidelines to capture the moment in High Park, underneath a stunning cherry blossom tree is a makes a romantic, old-fashioned way to propose. Just time it properly: they’re only in bloom for a couple of weeks in late April/early May. Also, you may want to go on a weekday if you can get time off; otherwise, you’ll be sharing the moment with dozens of photo-snapping others.
Simbar Mai/Flickr
2. During a Sunrise Run Along the Lake
If you’re an early rising couple who likes to bond during workouts, suggest a very early morning run right before the sun rises, running east, of course. Stop to “tie your shoe,” “because you have a cramp,” or simply to take in the view, then grab that ring from your (zippered!) pocket and drop to your knee. Not only is the Toronto sunrise just as stunning and picturesque as the sunset, you’ll likely have the view and the moment to yourself as the rest of the city (aside from the occasional fellow jogger) has yet to wake up.
3. At a Raptors or Leafs Game
A sporting event proposal sometimes works well, especially if a basketball or hockey game is your typical date night activity of choice with your significant other (SO). Just make sure you know that a) she/he is definitely going to say yes, and b) that she/he’s ok with hundreds of eyes watching on. Otherwise, it could go south really quickly – and will ruin the game for you forever.
4. The Distillery District
Year-round, The Distillery District is somewhat typical but always picturesque place to pop the question. Whether it’s on the Ferris wheel at the Christmas Market, during a summer’s night walk through the historic premises, or – if you want to get cheesy about it – in front of the heart sculpture, the Distillery District makes a solid (although obvious) choice.
5. Doing the CN Tower Edge Walk/Glass Floor
Sure, the CN Tower is a little cliché. But seriously, when was the last time that you rode the elevator up to the top? It’s probably been years. Make the engagement even more thrilling by doing so while hanging 1,168ft feet in the air during the Edge Walk, or – if that’s too ambitious – on the glass floor.
6. On a Ride at Canada’s Wonderland
Tap into your inner kid, and plan to propose mid-ride at Canada’s Wonderland. The key here is to keep the ring safely zipped in a pocket during the ride during the ask, then doing the whole down-on-one-knee thing once you’re back on the ground. This will be the one time that purchasing the ride shot will be worth it.
7. Post-dinner at the One Eighty
If you’re looking for a proposal with a view (that’s complete with a side of great food and wine), head to the One Eighty, located on the 51st floor of the Manulife Centre. Either ask the question during sunset (if it’s not occupied, walk over to “check out the private lounge” for a more intimate moment and best sunset view), or post-dinner, when the city lights as backdrop works just as well.
8. Mid-hike at the Scarborough Bluffs
Until you’ve been, few people realize the beauty of the Scarborough Bluffs. It literally feels like you’re nowhere near Toronto anymore. Bust out your runners, pack a picnic (complete with some celebratory champagne), and head east with your bride or groom-to-be and the ring.
9. At a Paintlounge via the Artwork
Book a special date night at Paintlounge, and make a deal not to look at one another’s works of art until they are completed (you know where this is headed). Whether your masterpiece is a painting of a ring, you on one knee, or simply the words “Will You Marry Me,” your partner will know your desire to make them your family as soon as you reveal your easel.
10. On the Stairs of the Four Seasons Centre After the Opera or Ballet
The stunning, glass-filled Four Seasons Centre adds to the “special factor” of a night at the opera or the ballet. After the show (but not immediately after, that’s when the stairs are full of fellow performance-goers – take a very long “bathroom break”) continue the fairytale-like theme of the evening and get down on one knee at the top of the stairs in the stunning venue. Or, if you trust your balance skills, midway down the stairs works too.
11. On a Sunday Stroll Through Graffiti Alley
Sure, graffiti may not be the most traditionally romantic thing in the world. But if cliche isn’t your thing, and street art is, a proposal in Graffiti Alley during a weekend walk may be a good idea, especially if you have someone hiding in the alley (which sounds a lot creepier than it is) to capture the moment. The colourful graffiti makes for eye-popping pictures, both during the proposal and for the inevitable “she/he said yes” social media post.
Missy S./Flickr
12. In the Middle of the Holiday-Light-Filled Old York Lane
Yorkville is the prettiest in the winter months, when the street lights and trees are adorned with quaint holiday lights, offering a classic Charles Dickens-esque Christmas feel, especially if snow is involved. After dinner at one of Yorkville’s restaurants (perhaps a sensory-stimulating meal at MoRoCo, complete with a takeaway of macaroons), stroll down Old York Lane and pop the question while the holiday lights illuminate your ring.
13. Skating at Nathan Phillips Square or Harbourfront
Really, what’s more romantic than a little skating date? Popping the question during a late night skate session (when the screaming kids have gone to bed) will never go out of style in the classic romance department. Not to mention, it’s more impressive to get down on one knee when skates and ice are involved. If it’s been while since you’ve busted out the skates, you may want to take a day off work to practice.
The City of Toronto/Flickr
14. Riverdale Park After a Walk
A proposal at the top of the Riverdale Park at the end of a quiet walk through the surrounding residential streets has two key elements for a perfect proposal: a stunning view of the city and a park bench. If you time it right on a summer night, you may even be able to catch the ice cream truck for a sweet celebration.
15. On the Toronto Island
While it’s an obvious addition to the list, the proposal possibilities at the Toronto Island are pretty much endless. Whether you pop the question over a champagne on the beach, during a bike ride from one end to the other, or on the ferry (or water taxi) ride home as you take in the view of the city from the water (which will never get old), “the island” is always a good option.
wonkanerd/Flickr
16. The Stairs at the Fairmont Royal York
Surprise your significant other with a “staycation” at the iconic, and ever-classic Royal York Hotel. With its rich history and regal decor, there’s something distinctly special and romantic about a visit to the hotel. Pop the question on the stunning stairs within its front doors, then go celebrate with champagne at the dimly lit Library Bar before taking it up to the room.
17. During a Picnic at Trinity Bellwoods Park
If your low-key lover has a thing for lazy, hazy days in Trinity Bellwoods Park, surprise your SO with a picnic in the park and don’t forget to pack the ring. Make a playlist for the day that will forever become your “engagement playlist” and bring along speakers and a blanket.
margonaut/Flickr
18. Le Papillon on the Park
Thanks to its fireplaces and rooftop terrace with its view of the city, Leslieville’s Le Papillon on the Park is one of the most romantic restaurants in the city, if you’re feeling the restaurant route. Its French cuisine will come with a side of a French kiss (had to) once she/he says yes.
Other notable mentions include the historic Casa Loma and the flower-filled Edward’s Gardens.
There you have it; now you just need the ring (and perhaps to find your future bride or groom).