If you’re new to Toronto, or even just the downtown core, it can be tough to navigate the best dating spots. And, of course, who are you to go on a subpar date? Before you know it, the hot and heavy beginning of the semester will be over, so don’t miss your chance to ask out that person you made awkward eye contact with in tutorial.

Here’s a dating guide to the city, tried and tested and tested and tested by yours truly. Broken down by personality type for your convenience:

You’re a classic U of T student who has either just discovered the Annex or a neighbourhood ride-or-die

Don’t mistake any snark in the subheading for a disdain for the Annex; I fall into the latter category described above. My highly-specific recommendation is to not eat at Sakura Sushi — I used to live above it. Instead, focus on the neighbourhood’s archaic but charming stores. BMV, with its books and records, is a place to get lost in before finding yourself asking how Queen Video is still around. Inti Crafts is a fun place to look for quirky bits and bobs (hey, do you want to come back to mine and decorate?). Grab dinner at Victory Cafe or Sushi on Bloor Street West before drinking something cheap at The Lab, likely in excess. Definitely finish the night with cake at Future Bistro.

You’re appropriately hip with a flair for art and vintage

Hit up the Art Gallery of Ontario and take advantage of the free admission deal, before swinging down to Queen Street West for thrifting at Black Market and a meal at Queen Mother Cafe. Proceed to join the throngs of tourists and suburbanites for the parade west on Queen until you grow tired. If you make it to Bellwoods, you win — pass GO and collect $200.

You’re appropriately hip with a flair for art and vintage AND willing to travel

Hit up the Museum of Contemporary Art and think hard about taking advantage of the partner deals at the nearby Henderson Brewery and the Drake Commissary — before doing just that. Try your hand at thrift shopping at the Bloor Street West and Lansdowne Avenue Salvation Army and, if it’s a Thursday, don’t miss the Dufferin Grove farmer’s market. Be sure to hit up Sugo for dinner — be prepared to wait — and Burdock Brewery for drinks. If you walk back east: trust me, Christie Pits Park at night isn’t as romantic as you’d think — probably the harsh lighting or something.

You’re bougie — or at least your parents are

Admittedly out of my own wheelhouse. Start with the most expensive coffee ever at Goldstruck, before browsing Bloor Street West’s luxury shops and hoping you’re the sugar baby in the relationship. Have dinner at — and these are unironic, good picks — Alobar Yorkville or Trattoria Nervosa. The Gardner Museum and Toronto Reference Library provide some lighter culture and architectural interest on the fringes of this neighborhood. But that might spoil the vibe.

You’re a genuine foodie and want to get stuffed 

Toronto is a great food city, and I can’t just recommend a restaurant or two. If you want to sample a wide variety of goods, and more generally immerse yourself in food culture, I’d tell you to start in Kensington Market. Sanagan’s is the best butcher in the city and is next to maybe the best bakery, Blackbird Baking Co. Nearby is Global Cheese Shoppe, Wanda’s Pie in the Sky, and a few minutes away is Carlos’ House of Spice. From there you can easily make your way into Chinatown to lose yourself, or walk along Dundas Street to find whatever the coolest new eat is.

You’re dedicated to making a park hangout work as a date

You have two fundamental choices to make: west or further west. Pick up drinks and food along Queen Street West — takeout tacos from Grand Electric will not let you down — and cross the street into Trinity Bellwoods. If you’re a bit more adventurous, get on public transit and head to High Park, which is a much bigger, better, and more private park. There are some great bars and restaurants in nearby Roncesvalles, with Bar-Que, La Cubana, or Bandit Brewery being my recommendations, and I guarantee your classmates won’t have been to any of them.

You’re sporty and actually healthy

You think I fucking know? Go do hot yoga and eat the less-tasty things on the menu at Urban Herbivore.

You’re obsessed with the outdoors

The relative isolation of urban nature spaces may not be the best call for a first date. But who am I to tell you what to do? Ride your bikes through the Don River Valley to the Evergreen Brick Works for a picnic and pose for hot Insta pics. Depending on the day there could be some pretty cool events there, like the Saturday Farmers Market. For something a bit more strenuous and away from the hustle, ride out to the end of the Leslie Street Spit through Tommy Thompson Park — the best place for birdwatching in the city. Plus, what if we kissed at the southernmost tip of mainland Toronto?

A catch-all winter edition because the cold equalizes all personalities

Browse the bustling St. Lawrence Market, where the only game in town for lunch is Carousel Bakery or Mustachios. Then go buy some of the best groceries at the city to cook later in the warmth of your shitty apartment or dorm. Recommended nearby activities include ice skating and hot chocolate at the Harbourfront Centre.

Disclosure: Jack Denton was the 2018–2019 Editor-in-Chief of The Varsity.