Date Ideas
To help take the guesswork out of date planning, I’ve made a list of my favourite restaurants and activities. If you have your own ideas for our party for two, you’ll find me to be up for pretty much anything. (Quail hunting? Sure, why not.)
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FOOD AND DRINK
Care for a pint?
There are so many cool pubs and breweries in Toronto, which can be perfect if you feel most comfortable with a more casual scene. They’re also great for shorter dates. (If you prefer not to drink, no pressure – these places offer 0% beers!) Here are a few of my faves, though Toronto has many more…
Downtown
- Mascot Brewery, King St W & Simcoe St – Just a 10 minute walk from my place!
- Collective Arts Taproom, Dundas St W & Markham St – They make great coffee too
- Bellwoods Brewery, Ossington Ave & Dundas St W – Great vibe & location
- Steam Whistle Taproom, Bremner Blvd & Lower Simcoe St – Right next to CN Tower & Rogers Centre
- BeerTown Public House Toronto, University Ave & Wellington St W – Not a brewery, but they have a great rotation of craft brews
Not-so-Downtown
- Blood Brothers Brewing, Geary Ave & Dufferin St – This one’s a fair distance from downtown, but about a 15 minute drive from Yorkville… and worth the journey
- Godspeed Brewery, Coxwell Ave & Eastwood Rd – They also serve WVRST!
- Left Field Brewery, Liberty St & Atlantic Ave / Gerrard St E & Greenwood Ave – A personal go-to for me! Left Field has a Liberty Village location in the west end and a Leslieville spot in the east
Coffee Date
While I usually have enough energy to keep us both going, a coffee date – maybe followed by a stroll? – can be the perfect mid-morning or afternoon date.
- De Mello, The Well – An old favourite of mine, now at The Well, within walking distance of my condo
- Fahrenheit Coffee, Portland St & Richmond St W – Great neighbourhood coffee
- The Library Specialty Coffee, Trinity Bellwoods Park – Perfect spot for an espresso and stroll through Trinity Bellwoods
- Goldstruck Coffee, Yorkville – Near the Park Hyatt, at Cumberland St & Bay St
Dinner Dates
I love good food. (Crazy, right?) There’s really no better way to get to know someone than sharing a delicious meal together. I hope you won’t mind me sitting next to you when possible – I like to get cozy.
I eat everything and have an adventurous palate (within reason… I can’t say Balut appeals to me much). I’ve made a list of a few local favourites of mine, as well as places I’d like to try, but I’m up for just about anything.
Downtown
- JaBistro, University Ave & Richmond St W – A refined yet unpretentious sushi and sashimi spot offering a casual take on Omakase
- Alo, Spadina Ave & Queen St W – Upscale, contemporary French (typically requires advance reservations)
- Byblos Downtown, King & John St – Delicious Eastern Mediterranean cuisine
- Rodney’s Oyster House, King St W & Spadina – A great, casual vibe with dependably incredible oysters (and caviar)
- Le Sélect Bistro, Wellington St W & Spadina Ave – I once saw Margaret Atwood dining here, so I consider this place holy ground
- Lee, Richmond St W & Portland St – Come for the Singapore-style slaw and stay for… well, everything else
- Jacobs & Co Steakhouse, CIBC Square – I’ve never been, and would love to!
- Nobu Toronto, King St W & Blue Jays Way – Located within steps of my condo!
- PAI, Adelaide St W & Duncan St – Casual (and delicious) Thai food
Ossington/ Trinity Bellwoods
- Union, Ossington Ave & Queen St W – Canadian-French bistro offering local ingredients
- Le Swan, Queen St W & Shaw Ave – An art-deco style French diner and one of my favourite little spots
- Mamakas Taverna, Ossington Ave & Queen St W – Elevated Aegean cuisine
- La Banane Toronto, Ossington Ave & Dundas St W – Maybe my current favourite French restaurant with amazing cocktails
- Côte de Bœuf, Ossington Ave & Dundas St W – A cozy spot for delicious farm-sourced meats and French cheeses
- and/ore, Ossington Ave & Queen St W – Modern Canadian cuisine served in a Victorian-inspired fantastical setting
West End
- Yasu Toronto, Spadina Ave & Harbord St – The best omakase in the city – to die for
- Bar Isabel, College & Shaw St – Contemporary Spanish Tapas-style dishes
- Antler Kitchen and Bar, Dundas St W & Dufferin St – Unique, seasonal menu featuring local wild and foraged ingredients
- DaiLo, College & Bathurst St – Incredible French-inspired Chinese cuisine
- Milou, Dundas St W & Gladstone Ave – A French bistro in Little Portugal, open all day every day
- Bar Raval, College & Bathurst St – Spanish pinxtos bar with great cocktails and stunning wood panelling
East End
- ēst Restaurant, Queen St E & Broadview Ave – Intimate setting with contemporary French courses and wine
- The Rosebud, King St E & Sumach St – A cozy French wine bar in Corktown
- The Wood Owl, Danforth & Greenwood Ave – A quaint retreat with good food on the Danforth
- Cherry Street Bar-B-Que, Cherry Beach – No restaurant list is complete without a BBQ spot!
North-ish
- Barberian’s Steak House, Yonge St & Dundas St W – My favourite steak house with old school vibes and a great wine list
- Adega Restaurante, Bay St & Dundas St W – Intimate spot for Portuguese and Spanish seafood
- Actinolite, Ossington Ave & Hallam St – Evolving set menu featuring in-season and local Ontario ingredients
Yorkville
- Adrak Yorkville, Avenue & Davenport Rd – Flavourful and decadent fine Indian cuisine
- Alobar Yorkville, Bloor St & Avenue Rd – Delicious seafood and meats, with a great wine list and amazing cocktails
- Amal Toronto, Bloor St W & Queens Park – Modern presentations of classic Lebanese dishes
- Osteria Giulia, Avenue & Davenport Rd – Fine Italian cuisine with a refined atmosphere
ACTIVITIES
Sporty Spice
When I’m not playing hockey, I’m watching it. And though I don’t play any of the games ending in ball, there’s nothing like the atmosphere of live sports.
- Jays games – I love the vibes at a Jays game: beers, hotdogs,… and not to brag but I look pretty good in blue
- March – September 2025
- https://www.mlb.com/bluejays/schedule/2025/fullseason
- TFC games – This isn’t the Premier League, but TFC games can be a ton of fun. The stadium also has gorgeous views of the lake and city at sunset
- March – October 2025
- https://www.torontofc.ca/schedule/matches#competition=all&date=2025-04-20
- Leafs games – The good ‘ole hockey game is the best game I can name
- Preseason September – October 2025
- Regular Season October 2025 – April 2026
- https://www.scotiabankarena.com/teams/detail/toronto-maple-leafs
- Raptors games – A great excuse to show off my cutest sneakers
- Preseason October 2025
- Regular Season October 2025 – April 2026
- https://www.scotiabankarena.com/teams/detail/toronto-raptors
- Hockey Hall of Fame – Somehow I’ve never visited!
- In my world, spa days are an integral part of any fitness routine
- Skating lessons from Cassie – Skating isn’t just for the winter! Let’s rent ice and go for a spin
Fun & Games
Watch my competitive streak come out over a game of table tennis, bowling or air hockey.
- Bowling at National, The Well – This place has great bowling and the snacks are delicious. There’s also an arcade!
- Table tennis at Spin, King St W & Spadina Ave – Admittedly I’m not the best at table tennis, but still find it a ton of fun
- Mini golf at Par-Tee Putt, John & Adelaide – These tiny courses are adorable
- Billiards – I really suck at pool, and would love someone to help me learn!
- VIP Billiards & Lounge, College St & The Danforth
- https://vipbilliardsclub.com/toronto/
- Arcade at The Rec Room, across from the Rogers Centre
- Retro arcade at Tilt Toronto, Queen St W & Dufferin St
- Board games at See-Scape, Keele St & Dundas St W – This is a true dive bar and not for the faint of heart! If you like weird vibes and weirder cocktails (and don’t mind an Uber drive to get there) this place is a lot of fun.
Into the Wild
… Meaning the wilderness of Toronto. I’d love to join you for a walk, hike or bike ride.
- Toronto Island
- Scarborough Bluffs
- Evergreen Brickworks
- High Park
- Rattlesnake point, Milton
- This one is longer, and further outside Toronto
- Columbias, not Vans, suggested for this one
- https://www.conservationhalton.ca/parks/rattlesnake-point/
Adrenaline Pincher
While I won’t be jumping out of a plane any time soon, I definitely enjoy a good adrenaline rush. Nothing like a bit of a thrill to make me squeeze your hand a little tighter.
- CN Tower EdgeWalk – Full disclosure: I have chickened out in the past. But I think I can do it this time (really!)
- Toronto helicopter tour – A bucket list item for me
- Axe throwing – I may need you to sign a liability release form beforehand (just kidding?)
- There are a few options, but Escape Manor Toronto is near my condo at King & Spadina
- They also have escape rooms. You be Velma, and I’ll be Scooby-Doo… eating snacks and cheering you on
- https://www.escapemanor.com/toronto
- Snuggles and scary movies – I loooove scary movies, and they provide a great excuse to get a little closer under the covers. (This idea is not limited to scary movies… we can also cuddle and watch Before Sunrise.)
Dancing (and Laughing) Queen
Music is most definitely the soundtrack of my life. I’m always attending concerts – it’s genuinely one of my favourite things to do, especially in the spring and summer. I’ve compiled a list of upcoming events (including comedy) I’m itching to attend. If our taste in music aligns, I’d love to hold your hand and get lost in the rhythm.
I enjoy music of all genres… seriously. Below you’ll find rock, rap, jazz, classical, the opera and everything in between, listed by date.
- The Practically Hip
- August 21, 2025 at The CNE
- This one is a bit weird… I love The Tragically Hip and don’t mind pretending with a cover band
- They’re playing at The CNE so this date also includes deep fried Oreos
- https://practicallyhip.com/dates.html
- Blue Rodeo
- August 23, 2025 at Budweiser Stage
- https://www.livenation.com/event/1AvZZbJGkllEN8m/blue-rodeo-with-special-guests-allison-russell-and-aysanabee
- Nine Inch Nails
- August 23, 2025 at Scotiabank Arena
- https://www.scotiabankarena.com/events/detail/nine-inch-nails
- The Black Keys
- August 31, 2025 at Budweiser Stage
- https://www.livenation.com/event/1AvZZbJGkSldNlB/the-black-keys-no-rain-no-flowers
- John Mulaney
- September 2 – 5, 2025 at Massey Hall
- https://masseyhall.mhrth.com/tickets/john-mulaney/
- System Of A Down and Deftones
- September 5, 2025 at Rogers Stadium
- https://www.ticketmaster.ca/system-of-a-down-deftones-with-toronto-ontario-09-05-2025/event/1000618BA61C10DC
- TIFF 50 – I’d love to see a film’s premier!
- September 4 – 14, 2025 at various theatre venues
- https://tiff.net/films?schedule
- Hozier
- September 10, 2025 at Rogers Stadium
- https://www.ticketmaster.ca/hozier-unreal-unearth-tour-2025-toronto-ontario-09-10-2025/event/1000623D892C0BF4
- The Pogues
- September 10, 2025 at History
- https://www.ticketmaster.ca/the-pogues-rum-sodomy-the-lash-toronto-ontario-09-10-2025/event/1000627D2F74646E
- Morrissey
- September 13, 2025 at Budweiser Stage
- https://www.ticketmaster.ca/morrissey-toronto-ontario-09-13-2025/event/100062BFEB1E598A
- Lorde
- September 24, 2025 at Scotiabank Arena
- https://www.scotiabankarena.com/events/detail/lorde-1
- Gounod’s Roméo et Juliette
- September 27 – October 18, 2025 at the Four Seasons Centre of the Performing Arts
- https://www.coc.ca/tickets/2526-season/romeo-et-juliette
- Sex Pistols
- October 1, 2025 at History
- https://www.historytoronto.com/events/detail/the-sex-pistols
- Whitney Cummings
- October 3, 2025 at The Elgin & Winter Garden Theatres
- https://tolive.com/Event-Details-Page/reference/Whitney-Cummings-2025
- Queens of the Stone Age – I’m a huge fan of theirs!
- October 5, 2025 at Massey Hall
- https://masseyhall.mhrth.com/tickets/queens-of-the-stone-age/
- Yusuf/Cat Stevens
- October 8, 2025 at Massey Hall
- https://masseyhall.mhrth.com/tickets/yusuf-cat-stevens/
- TSO – The Billy Joel Songbook
- Oct 8 & 9, 2025 at Roy Thomson Hall
- https://roythomsonhall.mhrth.com/tickets/new-test-page/
- Louis CK
- My all-time favourite comedian
- Oct 10 – 12, 2025 at Massey Hall
- https://www.stubhub.ca/louis-c-k-tickets/performer/182236
- Adam Sandler
- October 12, 2025 at Scotiabank Arena
- https://www.scotiabankarena.com/events/detail/adam-sandler-1
- Modest Mouse
- October 13, 2025 at History
- https://www.historytoronto.com/events/detail/modest-mouse-2
- The Rocky Horror Picture Show – This date features a sexy Halloween costume
- October 28, 2025 at Roy Thomson Hall
- https://roythomsonhall.mhrth.com/tickets/the-rocky-horror-picture-show/
- Stevie Nicks
- November 15, 2025
- https://www.scotiabankarena.com/events/detail/stevie-nicks-1
- Portugal. The Man
- November 27, 2025 at History
- https://www.historytoronto.com/events/detail/portugal-the-man-1
TRAVEL
Niagara
Only about 90 minutes from Toronto is the Niagara region, one of the most acclaimed grape growing and winemaking areas in Ontario – offering dozens of wineries, breweries, farm-to-table restaurants and quaint B&Bs. Of course, the area is also the home of Niagara Falls, the not-so-quaint Wonder of the World. Ready to explore with me on your arm?
While visiting Niagara, I’d say a wine tour is basically a requirement. Here are a couple that caught my eye:
- A private wine tour offering a selection from over 35 wineries in the region
- Here’s a bucket-list item I never knew I had: a helicopter wine tour
- Of course I had to include a tour which also has craft beer tastings, with both custom private tours and a public Something for Everyone tour
More info/options:
https://www.visitniagaracanada.com/
Prince Edward County
PEC is a couple hours east of Toronto, meaning it’s also not far from Ottawa, Montreal and Upstate New York. I haven’t had the chance to explore the area yet, but I’ve heard amazing things about the County – particularly the wine.
Here’s a tour that caught my eye: https://princeedwardcountycustomwinetours.com/ourtours
More info/options: https://visitthecounty.com/
Montreal
I don’t care what anyone says, Montreal is the best city in Canada.
… Okay that may be a tad bold, but I really love it. I also love that it’s only a short train ride from Toronto. The list of activities and restaurants in Montreal might rival those in Toronto, so I won’t add them here, but just know that I’m always thrilled to visit MTL for some romance. I can even pretend to like the Habs.
Abroad
All of the ideas above should give you a notion of who I am and what I love most in life. I’ve kept it local so far, but I often find myself yearning for experiences in more exotic destinations. I’m laid back, yet always full of energy, making me a great travel companion. Only down side? I sunburn easily, so I’ll need your help rubbing sunscreen all over. Hope that’s okay.
Consider me passport-ready and eager to embark on our next adventure.
