5 Holiday Date Ideas

There’s something about the Christmas and holiday season that is super romantic. Whether you want to or not, you get sucked into this world of watching people pick out the perfect gift for their loved ones (especially if you work retail), groups getting together to celebrate at parties and dinners, and couples perusing on the absolute cutest dates imaginable that either aren’t as magical the other eleven months of the year, or even possible to begin with.

Not sure how to fall into that holiday magic with your honey? Hopefully these five date ideas will give you some inspiration:



If you live in the Toronto area, the Distillery District puts on a fantastic Christmas Market every year, in one of the oldest areas of the city. From the lights, to the big tree, as well as a carousel for the kids (the big kids too!), to the many many booths showcasing independent businesses and the works of local artisans, a visit to the Distillery District in December can last from two hours, to a full day. Not to mention the fantastic restaurants that stand there all year round.

Though the T.O. Xmas Market charges patrons on weekends for entry, weekdays are free of charge regardless of whether you go bright and early, or towards the evening. Whether you do outdoor coffee and croissants in the a.m. or mulled wine the evening, it’s definitely a great place to go on a date – the heart with the mistletoe dangling above passersby is not to be missed either.

Alternative: If you live up north in the suburbs, and don’t want to deal with the craziness of getting to downtown Toronto, another option is heading to Unionville Main Street. One street, but lots of holiday spirit. On a weekend, you may be able to catch some Christmas Carollers as well!



20061208_The National Ballet_Nutcracker Dress Rehearsal

Bruce Zinger Photo

One of my fondest memories is my 2nd date ever with my boyfriend. We went to see The Nutcracker on December 30th (several years ago), and it was one of the most magical evenings I’ve ever experienced.From the theme of Christmas Eve in the story, to the glasses of champagne we shared during intermission, that date was even more exciting than our first one.

Follow the ballet with dinner followed with dessert, and the evening is sure to leave a lasting memory in your brain’s reservoir of “date nights”.




Something about hot chocolate and the holidays that just go hand-in-hand. Somehow it tastes better when there’s Christmas music playing in the background than when it’s just the lousy month of February. Whether you prefer something sweet, or a dose of caffeine, it’s a great opportunity to not worry about what you’re doing, but actually enjoy the moment together.

Toronto has some great aesthetically-pleasing cafes, and chances are the more caffeinated beverages they create, the less crowds you’ll run into after the sun sets. Here’s a few to get you started: Bobette & Belle, Dineen, Maman Bakery, Aroma Espresso Bar, Balzac’s.




This may not be everybody’s cup of tea, and certainly not the top most romantic date idea, but boy is it a lot of fun. There’s nothing quite like seeing your boyfriend get worked up over “that horrible pass” and “what was he thinking”.

Put on your jerseys, dish out on a couple of overpriced beers and popcorn, and just get rowdy and enjoy the moment. The adrenaline you’ll get from cheering on your team (and most likely getting angry at them, if you’re from Toronto) is incomparable, and will leave a fun spirit within you for the next little while.



Ah yes, a timeless classic, Sunday Brunch. Heck, if your schedule allows it, go on a weekday and avoid the crowds. The best way to truly enjoy it with your SO is if you’ve got nothing planned for the rest of the day, and you can shamelessly indulge in as many mimosas as you’d like.

Whether you’re going for full out indulging in pancakes with ALL the works, or want to stay somewhat healthy and stick to your salmon eggs Benny, brunch is always a good way to spend some time together when there’s no rush, and you can enjoy each other’s company all refreshed right after a good night’s sleep.


Whether you’re on a budget, need an excuse to dress up, or just want to get loud and support the home team, these five date ideas are just the start to a holiday season of romantic moments.

What’s your favourite date to go on during the holiday season?


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