Hallmark holiday or not, Valentine’s Day is here to stay. This February 14th, we’ve decided to embrace the chance to celebrate our loved ones; after all, this winter could use a healthy dose of heart-shaped fun as a reprieve from the -20 wind chill. As we finalized our V-Day plans for 2026, the SHARP editorial team decided to jot down a few Dos and Don’ts this year. Read below to discover hot takes and horror stories.
Things to Do This Valentine’s Day
Let’s start off positive — here are four pro tips to get Cupid’s celebration right.
1. Communicate Your Needs
“Communicate, communicate, communicate. Though so many of us were raised with the idea that we’re supposed to just inherently know what our significant other wants and needs, humans can’t read minds. Talk to your partner about the holiday and what it means to them — there’s no better way to ensure you’re both on the same page about what really matters this Valentine’s Day. That said, there’s nothing wrong with a good surprise if you feel like trusting your gut.”
— Justin Mastine-Frost, Director of Digital Content
2. Celebrate V-Day A Tad Early (Or Late!)
“If you’re planning to go out for dinner, go the night before or after. Reservations are easier, and the crowds are smaller. Also, flowers and chocolates are always a good idea.”
— Haley Dach, Fashion Director
3. Find A Place Your Partner Has Been Dying to Try
“Take note of the restaurants that catch your partner’s eye throughout the year. For me and my fiancée, sharing a good meal is one of our favourite experiences together, and has given us countless core memories. Even the small moments like “Oh, I love the look of the bar” or “My friend ___ said ___ was amazing” plant a seed. In the weeks leading up to the day, feel free to sprinkle a few different reservations around the aforementioned spots, bring each restaurant up casually in conversation, and stick with the one that still seems to capture their excitement most. It shows you’re listening, it shows you’re excited and intentional about sharing the experience, and if all goes well, you get a great meal out of it. It’s a win-win-win.”
— David Stol, Managing Editor
4. Add A Thoughtful Surprise to Go With Your Gift
“Make your partner’s life easier. By mid-February, the long nights and freezing temps take a toll on all of us — little gestures will go a long way. Whether that means putting gas in their car, scheduling a surprise cleaning spree before they get home, or stocking the pantry with their favourite snacks, small conveniences like these will make your partner’s daily grind a tad lighter. Just don’t forget to grab something you can gift-wrap, too.”
— Cormac Newman, Associate Editor
Here’s What Not To Do This Valentine’s Day
And, to evade an awkward scenario, here are some things to avoid this Valentine’s Day.
1. Be Nosy
“Don’t ask people that you aren’t close with about their plans for Valentine’s Day. Let them tell you if they want to share, but everyone treats the holiday differently, and it can carry a lot of emotion for some (either positive or negative).”
— Justin Mastine-Frost, Director of Digital Content
2. Forget Your Valentine’s Proposal
“Don’t forget to ask your special someone to be your Valentine! Being cheesy makes life (and love) more fun.”
— Haley Dach, Fashion Director
3. Mess Up Their Skincare Routine
“Don’t try to reinvent the wheel, and by wheel, I mean her skincare/makeup routine. Look, I know men are evolving in their skincare. And thank goodness. But let’s not let our hubris be blinding. The truth is, you (probably) don’t know better than her when it comes to what works best for her skin/complexion/personal taste. Instead of grabbing the most expensive product from the buzziest brand in some Hail Mary attempt to signal “I remembered!”, pay attention to the items she’s constantly using and stock up. If you want to go a step further, note down the products, and when you’re at a specialty skincare store, ask which complementary product would be a dream for someone with her skin routine. Sometimes it’s about leaving it to the experts and, as painful as it is to admit, sometimes, we’re not the experts.”
— David Stol, Managing Editor
4. Let Expectations Ruin the Excitement
“Don’t put too much pressure on things. Holidays tend to crumble under weighty expectations. However your plans shake out, don’t forget what Valentine’s Day is meant to be: an occasion to celebrate the way you feel about your partner. So, while we can’t all snag the best seats in the restaurant, we can make an effort to enjoy dinner.”
— Cormac Newman, Associate Editor
