14 Toronto Bars To Bring A First Date To Ensure You’ll Get A Second Date
Tried, tested, and true.
Photo cred - Jason Cook
So you’ve met a babe, whether it be on the online or in the real life, through a friend, on the street, or on Tinder or OkCupid. IRL or URL, this is someone that you want to take out.
But where the hell do you go?
Maybe you don’t know Toronto that well. Maybe you just want a new suggestion. But whether or not you’re looking to get it in tonight, we’ve got a list of bars you can take your new beau, from the best dive bar around to some places that are a little more upscale, depending on your standards and the cash you have on hand.
Peruse at your leisure, and hopefully settle on something before you rush out out the door, so you at least have an inkling of a plan of what you two will do tonight.
537 Queen Street West
Literally the best place in Toronto. Don’t bother going anywhere else. This is the best, the pinnacle of everything you’d ever want in a bar: Cheapest drinks around, cheap and moderately decent food, a large patio for those perfect warm evenings, and the best haggard-looking bar vibe yet. I go to Java on the regular-- this place makes a comfortable and chill setting for a first date.
Photo cred - Uncle Lynx
Ronnie’s Local 069
69 Nassau Street
I have had my share of misadventures at Ronnie’s, and I’m only putting this on the list because it’s a straight up awesome small bar in the heart of Kensington. Surely you will both get so drunk your new flame will think you are a thousand times more charming and funny than you really are. Of course, then you’ll have to come back. Oh, and it’s right across the street from The Grilled Cheese. Which, if you order and then hit up the bar, delivers.
Thirsty & Miserable
197 Baldwin Street
Oh look, they named a bar after me. This place doesn’t get as packed as Ronnie’s and Java, at least not in my experience. They’ve got good, local ciders available (for those non-beer drinking folks) and it’s small and seems pretty #tough. It just feels cool when you’re in there.
60 Kensington Avenue
A mystery. Just kidding-- it’s at 60 Kensington Avenue. Good luck finding it.
I was taken here for a second date once and I’ve never been more impressed in my life. A sort of literal hole-in-the-wall, you have to know where it is to find it. It’s 24 hours and ALWAYS popping. I’m not gonna tell you where it is, but if you know, you will know.
458 Queen Street West
This place plays the best music, none of that Top 40 stuff most of the bars play (though I dig that as well)-- it kinda varies from . It’s laid-back, got a really fun atmosphere, affordable pitchers (for that inevitable initial awkwardness), and a pretty decent tex-mex menu going on too. The patio has fairy lights strung up, which just makes me love it more.
Hair of the Dog
435 Church Street
A “fancier” bar on Church Street, it’s one of the few places in Toronto that serves Delerium on tap, along with a load of other imported beers. It’s a bit pricier with food than your local hole-in-the-wall, but the boozy selection and elegant ambiance makes up for it.
431 College Street
A Toronto icon, Sneaky Dee’s is the place to be if you are having a group date. Always bumping and selling the best atmosphere, this disgusting local filthhole is the best filthhole around. Not to mention that the all-day breakfast is, potentially, to die for.
Free Times Cafe
320 College Street
Not as popping as its Kensington counterparts, this College Street place has the best laid-back vibe for a casual first date, and it’s fairly roomy. I suggest wearing plaid. The latkes are also nice comfort food if you’re in the mood to grab eats.
Photo cred - The Empty Room
334 Queen Street West
Eleven pool tables make for an open-ended first date as you can awkwardly try to impress each other with your horrible drunken pool skills-- or you can just get drunk. A true Toronto joint, we’ve all started or ended our nights here, in the best or worst of ways. Located right on Queen West, if you leave, there’s still a lot to get up to in the nearby walking area. The Rivoli is also a common setting for shows and concerts.
600 King Street West
For the beer connoisseur couple looking to talk about their love of the wheat beverage together. Not for the gluten-intolerant-- if you took a Celiac here, I doubt drunk fun would be had. Still, the King West location is large and beautiful-- much more elegant than any of the dive bars already on this list, and offering a decent excuse to dress up.
295 King Street West
This happy-go-lucky place is right in the Entertainment District, so before (or after) a couple of drinks, you and your beau can see a movie or a play or whatever musical happens to be going on.
The Rex Hotel Jazz & Blues Club
194 Queen Street West
If you’re new to jazz or it’s all old hat, the Rex is always a cool place to be. There’s live music a lot of the time, and the place has a big enough patio to accommodate larger groups if need be. However, you can always stay inside with your date and watch the band play. The vibe here is always fun and exciting, and a lot of the time, the place is often packed. Grab a seat, grab a drunk, and enjoy the show.
13 Ossington Avenue
A bit of a more intimate atmosphere, this Ossington place is good for a low-key, first time meeting. It’s small and casual, perfect for a quick drink before heading out elsewhere-- or for staying the whole night and getting to know each other in this perfect, tiny setting.
Photo cred - Michael K N
This End Up
1454 Dundas Street West
This place has the best mojitos I’ve ever had in the city. And the reason you will get a second date is because they are expensive.