Things to Do Valentine’s Day in Toronto 2020

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Jully Black as Caroline in Caroline, or Change, photo courtesy Mirvish
Jully Black as Caroline in Caroline, or Change, photo courtesy Mirvish
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A Valentine’s Day dinner at a restaurant is a safe bet for the most romantic day of the year, but some years, you want to mix it up a bit. If you want to skip the fancy (and often expensive!) V-Day dinner, there are many other things to do Valentine’s Day in Toronto 2020 where you can spend time together doing something you both enjoy. Check out these fun Toronto events for Valentine’s Day 2020 below:

The Second City Totally Likes You

If you are looking for fun Valentine’s Day events in Toronto, you might want to attend Second City Toronto’s newest comedy show, The Second City Totally Likes You. The Second City comedy troupe mocks dating, sex, meet-cutes, and meet-uglies in this super-charged show that features classic material and brand-new sketches. This 90-minute comedy has two shows on Valentine’s Day Friday, February 14, 2020 at 7 p.m. and 10 p.m. Tickets are General $32 (you have to share a table) or Rail $52. Purchase tickets online or at the box office. You can add dinner at Wayne Gretzky’s (next door) for an additional $33.04 (two course) and $38.94 (three course). Second City is located at 51 Mercer Street, 416-343-0011.


Couples Massage at Novo Spa

Start Valentine’s Day off with a Couple’s Valentine’s Day package at Novo Spa in Yorkville that includes:

  • 55-minute Therapeutic Massage by Registered Massage Therapist
  • 15-minute Head Massage or Foot Massage
  • Couple’s private steam, jets, colour therapy shower
  • Beverage for two and chocolates
  • Red Rose

The Couples Valentine’s Day package is $410. Other Valentine’s Day packages include the Valentine for Two Couples package, $350, which includes a Rose Petal Foot Soak & Massage (15 min); Rose Salt Scrub (15 min); Chocolate Body Mask and Chocolate Mini Facial (40 min); couples private steam, jets, Colour Therapy Shower, beverages for two, chocolates and red rose.

Paint stations set up for Paint Nite at Midtown Gastro Hub in Toronto.
Paint stations set up for Paint Nite at Midtown Gastro Hub in Toronto.

Valentine’s Day at Paint Nite Toronto

Express your creativity at Valentine’s Day Paint Nite events on Friday, February 14, 2020 at 7 p.m. at Marche Movenpick; Fox and Fiddle; Originals Ale House; Pie Bar; Chelsea Hotel; The Rhino Bar & Grill; and Krepesz Cafe & Bar. Participants will paint a specific painting with step-by-step instructions provided by the class instructor. Cost is $45 plus tax. Read about Blogger Diana Condolo’s experience at Paint Nite.

Motherhood The Musical at Lower Ossington Theatre

Immerse yourself in the challenges and pleasures of motherhood in the comedy, Motherhood The Musical, at Lower Ossington Theatre. The musical focuses on soon-to-be first-time mom Amy; lawyer Brooke; mother-of-five Barb; and single working mom Tina. The show features the Billboard Top 10 comedy hit, “The Kids Are Finally Asleep;” plus “Costco Queen;” and “I’m Danny’s Mom.” Performances on Valentine’s Day Weekend 2020 are on Friday, February 14, 2020 at 7:30 p.m., Saturday, February 15, 2020 at 3:30 p.m. and 7:30 p.m. and Sunday, February 16, 2020 at 3:30 p.m. Tickets are $59.99 plus tax and service charge. Purchase tickets online or at the Box Office. Lower Ossington Theatre is located at 100 Ossington Avenue.

Taking Back Valentine’s Day

Enjoy a night of full tribute sets to Jimmy Eat World, My Chemical Romance, Paramore, Fall Out Boy & Thrice on Friday, February 214, 2020 by members of PONY, Pretty Matty, So Young, Weak Hands, Wild Black, Feels Fine, Nice Going & Baby Band. The event is a fundraiser for Supporting Our Youth, which works to support the health and well-being of queer and trans-spectrum youth. Doors at 8 p.m. $15/NOTAFLOF at Junction City Music Hall, 2907 Dundas Street West.

Valentine’s Day Couples Cooking Class at The Chef Upstairs

Looking for things to do Valentine’s Day in Toronto 2020 that are collaborative? Take the Couples Cooking Class at The Chef Upstairs, 516 Mount Pleasant Road, 416-544-9221 on Friday, February 14, 2020 at 6:30 p.m. You will cook the following four-course meal during the class: The class is also available at Vaughan location at Hwy 7 and Centre Street.

  • Complimentary glass of Prosecco to begin, served with flatbreads, dip, olives and cheese;
  • Seared Sea Scallop with red grapefruit and avocado;
  • Roasted Celery and Garlic Soup, topped with Crisp Prosciutto;
  • Bistecca alla Fiorentina: A 3” thick porterhouse steak grilled to perfection, drizzled with a balsamic glaze and served with sautéed greens, oven-roasted tomatoes and cannellini beans with olive oil, salt, and pepper;
  • Dark chocolate mousse with chocolate-dipped strawberries.

Beer, wine pairings and non-alcoholic beverages are available for purchase during the class. Cost is $250 per couple plus HST. All cooking classes are non-refundable and must be paid for when booked. If more than 7 days’ cancellation notice is provided to The Chef Upstairs by email or phone, you will be eligible to reschedule to a future class.


Jully Black as Caroline in Caroline, or Change, photo courtesy Mirvish
Jully Black as Caroline in Caroline, or Change, photo courtesy Mirvish

Caroline, or Change at Winter Garden Theatre

Valentine’s Day events in Toronto 2020 include the performance of Caroline, or Change starring Jully Black as Caroline and featuring Measha Brueggergosman. Caroline, a single mother of four, is a black maid working for a Jewish family in 1963 Louisiana. In response to suggestions that Caroline’s salary of $30 a week is insufficient, her employer tells Caroline that she can keep the pocket change she finds in the laundry. This act of racial condescension creates a moral dilemma for Caroline and symbolizes the imminent social and economic tensions in the U.S. The musical runs from Jan. 30 to February 15, 2020 with a performance on Valentine’s Day – Friday, February 14, 2020 at 7:30 p.m. – at the Winter Garden Theatre at 189 Yonge Street. Tickets are $129, $109, $89, $59, and $39 and can be purchased online.

Post Malone at Scotiabank Arena

Post Malone performs at Scotiabank Arena (formerly Air Canada Centre) on his Runaway Tour on Friday, February 14, 2020 at 8 p.m. Special guests include Swae Lee and Tyla Yaweh. Tickets $934, $819, $585, $502, $429 and $351 and can be purchased at Ticketmaster.

Afternoon Tea at The Ritz-Carlton, Toronto

Enjoy The Ritz-Carlton, Toronto’s Weekend Signature Afternoon Tea on Saturday, February 15, 2020 and Sunday, February 16, 2020 from 11 a.m. to 1 p.m. and from 2 p.m. to 4 p.m. Some of the delicious menu items include Smoked Salmon & Egg Sandwich; Lobster & Crab Salad Sandwich; Cucumber, Whipped Herb Brie, Lemon Zest & Watercress; Caramel Ganache Cake; Classic Pecan Tart; and Vanilla Mousse Tian. Cost is $54-$69. Call 416-585-2500 for reservations. The Ritz-Carlton, Toronto is located at 181 Wellington Street West.

If you have any suggestions for things to do Valentine’s Day in Toronto 2020, please leave a comment.

6 COMMENTS

  1. These would all be fun to do! I haven’t thought much about Valentine’s Day yet, but it is good to have some ideas and always good to plan ahead.

  2. So many date ideas for Valentine’s day! We don’t have any plans yet, but we can check on the events around our area and see what would be nice (and affordable).

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