Drinks and dinner always go down well for a date night, and there are plenty of options in Toronto's ever-evolving east end. The neighbourhoods east of Yonge are often underrated, but they can give the rest of the city a run for its money when it comes to excellent food and entertainment. From historic landmarks to lively pubs, your night will be popping at these date-worthy east end joints.
You’ll both feel relaxed at The Comrade, where the propaganda art and suave, retro decor is plenty chic while still unpretentious. The communist-themed imagery is strictly tongue-in-cheek, and no Soviet-era bar ever served drinks like these. The cocktails are arguably some of the best in Toronto and sure to keep your conversation flowing. Try the Earl Grey-infused bevvy or divine, white wine sangria. There are light eats like cheese and charcuterie boards, and a smoked salmon platter that’s great for sharing.
This cinema has been a neighbourhood fixture since the silent movie era. Opened in 1914, the Fox graduated to talkies and now screens slightly offbeat films that engage the mind and soul, but aren’t so weird that they’ll frighten your date away. A vintage lobby, seating area, and old-fashioned snack bar complete with popcorn machine, offer a comfortable backdrop to help you become acquainted.
If your timing is right and your date is a culture buff, you might catch an opening night reception at this eclectic, east end gallery space. It showcases work by exciting new and mid-career artists in group and solo presentations, paintings, collage work and photographs. The award-winning room will warm you up for a night of conversation that can be as highbrow as you want it to be.
Be brave. We dare you to bring your date here for the Tuesday “foofer” karaoke, where aspiring pop stars and shower-singers alike belt it out or croon romantic tunes. You’ll both get comfy in the underground ambience, elegant-industrial decor, and open, inclusive vibe. There’s a good mix of imported beers, including Kronenberg and Tetleys, and signature cocktails like the Tropical Buddha: a mix of Malibu, raspberry liqueur, ginger-pear and guava juice.
Treat your date to their favourite seafood dish; from oysters to clam chowder and fish tacos to ceviche, the smell of the sea is in the air. The acclaimed menu at Eastside Social is definitely ocean-oriented but also offers savoury main course salads and daily-fresh homemade pastas. Special menus on different weeknights add the element of surprise. It won’t just be dinner but an experience worth sharing.
By day, this Corktown locale feels like a Scandinavian heaven with its light wood, lofted ceilings and functional design. By night, the mood switches as the chic daytime space becomes a dusky, European-style bar serving draft and bottled beers and Canadian wines. Try it for a date night that’s classy but not over the top.
You can live in a town for years and never see some of its best attractions. Date night is ideal for checking out those places you think are reserved only for tourists. Invite your date to the brick and cobblestone lanes of The Distillery District. Whether you’ve been here before or not, it begs repeat visits for the mix of fine restaurants, shopping, and seasonal events set among the restored 19th-century warehouses.
You’ll get an A+ for sensitivity, romance, and originality with this date night selection. As the name suggests, Pocket Concerts presents chamber music in tiny venues like an office space, public library, or even your own home. Your tickets include an evening of music and post-concert reception. It can feel like a private serenade even in the midst of fellow music lovers. #Classy!
An underground theatre troupe known as Zero Gravity Circus rises from its deep pit of dysfunction to stage the Lunacy Cabaret, a talent showcase unlike any in the city. It’s an often wild and unpredictable night of vaudeville revivalism held several times a year on the site of a century-old theatre. Bring an open-minded companion for an evening of laughs and debauchery; if your date still likes you after this show, you’ve met your perfect match.
