I’ve written about my favorite date locations in Toronto before, but now I am a grown-ass adult. Just kidding. Very much not that. However, since writing that post, I did start dating someone who has much more refined taste than me in things like cocktails and fine dining, and he has introduced me to many places in my own city that I had no idea existed and had no idea I’d love so much. So I thought it might be time to revisit this series.
A note: many of these places are pricier than I would typically recommend, and I’m aware that that makes them inaccessible to many. These could become your go-to date spots if you’re well-off enough to make that happen, but if you’re like me, they’re likelier to become special-occasion-only sanctuaries. Or maybe you’ll convince your sugar daddy or grandfather or tech-bro friend to take you to one. Hey, I don’t know your life.
Northwood has become my favorite cocktail bar in the city. (BlogTO agrees. Be still, my heart.) The atmosphere is chill and relaxed, though still fancy enough that I don’t feel out of place if I get dressed up for a Northwood jaunt. They do a bunch of proprietary drinks as well as a whole host of classics, and if you have an off-menu special request, they’ll usually do that, too. I adore their Lady Grey Sour (a sharp and refreshing whiskey sour with, oddly enough, black pepper sprinkled on top) and Black Walnut (a cinnamon-y, nutty sour that’s perfect for fall); they’ve also made me many a Southside, my favorite cocktail, and it’s always wonderful. If Ilissa is working, you know you’re especially in for a treat. Crucially, I feel completely at home here whether I’m with a date or just by myself with a journal or book. This place is a fave and will remain a fave.
Insomnia is partly known for its late-night eats (hence the name) but I’ve mostly come here for lunch and brunch. Their French toast, eggs specials, and breakfast cocktails are all delightfully fancy and the food is very filling. I’m particularly enamored with whatever magical tomatoey sauce they put on their homefries. The atmosphere in here is bustling and you’ll probably have to wait for a table, but it’s worth it.
Jacobs & Co. is a fancy-ass steakhouse tucked away in a nondescript building. I felt like a queen tottering up and down their many staircases in my high heels. The staff is fiercely smart and knowledgeable; our server gave us an extensive spiel about every cut of steak on the menu and helped us choose the right main and sides for our preferences. You’ve gotta try the incredible Caesar salad, prepared table-side; we also loved our oysters and potato puree. And of course, the steak was out-of-this-world delicious. I was especially charmed that they were able to make me my favorite off-menu cocktail, the Southside (sensing a theme?), and that they sent us home with plastic-wrapped dinner rolls to enjoy later that night or in the morning. The attention to detail here is commendable.
Bar Isabel is a Spanish-inspired bar and restaurant that gets pretty much universally positive reviews from Toronto foodies. The seductively low lighting makes this place feel intimate and cozy, and the kitchen is open late (midnight most days, 2AM Fridays and Saturdays), so this is an ideal spot for a post-sex bite or a night-owl date. I love munching perfectly-cured ham and sharp cheese on bread and sipping cocktails while cuddled up to my love.
El Catrin is a Mexican restaurant in the heart of one of my favorite Toronto neighborhoods, the Distillery District. If you crave authentic Mexican food and drinks, this place is a must-do. I adore their chicken tacos, guacamole, and tortilla chips. Having a traditional margarita here also kickstarted a months-long margarita obsession for me, and honestly, I’ve been unable to find one I like better in Toronto than the ones made here.
La Banane is where my darlin’ taught me to eat oysters – aww! It’s a fancy French restaurant with a seafood-heavy menu. We loved sitting at the bar, where we could watch chefs handling seafood up close and chat with them a bit (my partner’s an extrovert, okay). We were impressed with how the staff went above-and-beyond to make us happy, and seemed genuinely invested in making sure our meal was great.
Auberge du Pommier is a French restaurant located, weirdly, in the otherwise quiet and humdrum North York. I was surprised to see such a beautiful, ornate place hidden in that area. We sat on the lush patio and sipped white wine while marveling at the gorgeous decor. I tried foie gras for the first time here, and it was prepared to perfection. The black truffle risotto here is also one of my faves I’ve had, and I say that as a confirmed risotto fiend.
Queen Margherita Pizza is a big, bright Neapolitan pizzeria with multiple locations; I’ve only been to the Dundas West one. As you might expect, their wood-fired pizzas are A++. I also dig their lavender old fashioned, though my boyfriend insists a drink can’t technically be an old fashioned if there’s lemon juice in it. Oh well; it’s still delicious. The waitstaff here are always friendly, whether I’m here with a friend, a partner, or just a book to read. I love sitting in the window here and people-watching while I eat.
Pray Tell is a hoppin’ bar with great brunch offerings. It’s truly the epitome of Fancy Millennial Food, with items like avocado toast and mochi donuts appearing on the menu. We enjoyed their unusual selection of cocktails and their goofy, friendly staff.
Civil Liberties is a cocktail nerd’s dream, but also a great place to go if you know nothing about cocktails and nonetheless want to drink some. They have no menu; you just ask for what you want, however vaguely, and the genius bartenders will bring you something cool. I’ve ordered “a refreshing sour,” “something with ginger or cinnamon,” “something like a Southside,” and so on, always with excellent results. The vibe of this place is usually a little louder and more crowded than I would prefer for an intimate date, but I’m a sensitive li’l introvert, so your mileage may vary. In any case, if you and your sweetheart can get a couple of seats at the bar, you’ll be able to snuggle up close and whisper seductively in each other’s ears while you sip your drinks.
The Broadview Hotel was built from the wreckage of ancient strip club Jilly’s, which I unfortunately never got to visit before it closed for good. At least its replacement is lovely, though. I haven’t stayed at this hotel yet, but I’ve been to both the ground-floor bar and the rooftop bar. Both are beautifully designed and serve tasty cocktails, but we preferred the rooftop bar for its better, faster service and (obviously) better views. If you’re looking for a great rooftop patio in the city, it’s hard to go past the Broadview (and the Drake).
What are your favorite Toronto date spots?