• Instagram - Grey Circle
  • Grey Twitter Icon

Dating in The Big City

With cuffing season just around the corner, it is more necessary than ever to have a good first date location in your back pocket at all times!

First dates can be awkward, uncomfortable, and downright awful – but if you’re lucky enough to have scored yourself the opportunity to have 1-3 hours of uninterrupted interrogation then consider yourself lucky! Finding a suitable match in the big city is a tough gig.

I’ve carefully crafted a list of the perfect first date locations with your comfort in mind! I’ve taken into consideration all the awkward road bumps and chosen the smoothest sailing locations to get you in a committed relationship in no time!

The first date is absolutely no time for ridiculous activities such as apple picking or skating or any other idiocrasy of the sort. Everybody just needs to sit down and talk it out, which is why I’ve devised the date ideas into bars, coffee shops, and for those of you feeling up to the challenge: a miscellaneous category.


Pumping yourself full of alcohol is a killer way to ditch the first date jitters and be your most authentic self – which is key when looking for love!

Bellwoods Brewery - 124 Ossington Ave, Toronto, ON M6J 2Z5

Wallflower -1665 Dundas St W, Toronto, ON M6K 1V2

Loveless -1430 Dundas St W, Toronto, ON M6J 1Y5

Pray tell - 838 College St, Toronto, ON M6H 1A2

Cocktail bar - 923 Dundas St W, Toronto, ON M6J 1W3

416 Snack Bar -181 Bathurst St, Toronto, ON M5T 2R

Coffee Shops

If you don’t want to get carried away on your first date and are keen on finding out if you and your potential life partner are genuinely compatible – then a coffee date is the move for you!

Boxcar social (many locations all over the city)

Ezra’s Pound -238 Dupont St, Toronto, ON M5R 1V7

El Almacen -1078 West Queen Street, Toronto, ON M6J 1H8

Manic Coffee -426 College St, Toronto, ON M5T 1T3

Quantum Coffee -460 King St W, Toronto, ON M5V 1L7

Rooster Coffee House -479 Broadview Ave, Toronto, ON M4K 2N4


Dabble in the miscellaneous category at your own risk – I would highly recommend these situations if you actually know your prey prior to the first date (i.e. do not attempt this as a Tinder date unless you consider yourself v ~chill~)

Park hangout – drinking, eating, watching the sunset

  1. Trinity Bellwoods

  2. Riverdale Park

  3. If you are feeling crusty – Christie Pitts Park

Ice cream/froyo date (v casual)

Toronto Islands

AGO – (Wednesday night is free if you want to be a cheap date)

Activity bar/cafe

snakes and lattes/laagers - 489 College St. Toronto, ON M6G 1A5

Track and Field Bar - 860 College St, Toronto, ON M6H 1A2

Get Well -1181 Dundas St W, Toronto, ON M6H 1Y3

Dundas West Video -831 Dundas St W, Toronto, ON M6J 1V4

I hope these suggestions ease your transition into cuffing season, and hopefully land you a second date and in the best-case scenario: a significant other!

It’s a dog eat dog world out there so don’t hold back!! Pull out all the stops!! Pre-drink every date!! And most importantly – smile and be yourself.

Good luck friends!

© 2020   Avenue24 Magazine.  All rights reserved.
Use of and/or registration on any portion of this site constitutes acceptance of our User Agreement (updated 1/1/20) and Privacy Policy and Cookie Statement (updated 1/1/20).  Your Ontario Privacy Rights  Cookie Settings  The material on this site may not be reproduced, distributed, transmitted, cached, or otherwise used, except with the prior written permission of Avenue24 Magazine.  Avenue24 Magazine may earn compensation on sales through affiliate programs.

  • Grey Facebook Icon
  • Grey Twitter Icon