You a hipster? Have an important first date coming up? Wondering what to do that will impress and show off your cool hipster style? Well, I’ve got the answer! Here is a perfect night out in and around Queen West that is sure to impress your date.

First and probably most important, make sure you look the part – put together an outfit that’s both cool and comfortable and reflects your hipster style. Start off the night when the sun is out – everyone looks great in a pair of Ray-Bans – and head over to Reposado on Ossington. Tequila cocktails and a cozy back patio are a combination that can never go wrong. Reposado features a list of tequila that is both extensive and exclusive, as well as a list of inventive tequila cocktails. And I’m not talking straight up margaritas – though those are awesome too, especially the mango flavoured one. But on a first date, go for something spicier like the Hot Ruby, which combines habanero-infused tequila and strawberry tequila resulting in a cocktail that tastes like a spicy strawberry candy. Tingles, anyone? Nothing better to start heating up your evening…

After a couple of cocktails, take a stroll down the street to Union. I love this place. Again, adorable little back patio and a vibe that is both romantic and French bistro-like. These guys take a lot of pride in what they do from their vibe, to their food to their wine list – and the prices are super reasonable. The menu is small but tasty, truly locally driven (the chef actually owns a farm) and offers a nice selection of sharing plates. I suggest starting off with a half dozen oysters – just a few each to keep that spicy tequila heat going – and follow that with the steak tartare. In my opinion, this tartare is one of the most traditional and delicious in the city. Coming from France, this classic dish is paired ideally with Dijon and warm butter toasted bread, and this is exactly how it’s served at Union. Mains are amazing as well and if your connection is strong, I suggest sharing a couple of those or if you’re both carnivores, go for the Cote de Boeuf for two – a prime rib from Scotch Mountain, Ontario served with frites and vegetables. Heaven on a plate, really.

You may decide to end your evening on this charming back patio sharing their delicious sticky ginger cake, which is simply divine. Or, if your connection is going strong, walk west on Queen over to the Melody Bar at the Gladstone Hotel. Named one of the top 10 bars in North America by Conde Naste Traveler, the Melody Bar has very cool contemporary art décor, late night live music, and unique cocktails. It’s cozy and cool at the same time. The Melody Bar is the cherry on top of the perfect recipe to end your night on a high note. Trust me, your date will be so impressed with your choices to create the perfect first rendezvous, you just may get lucky.

Liked this post? Next week I will create the perfect date for two competitive adventure seekers living in a big city. And, if you want any other restaurant advice, email me!

Photo courtesy of Reposado’s Facebook page