Valentine's Day date ideas for every stage of a relationship

Posted by Jen Kirsch, February 13, 2017
Neon Heart

When it comes to Valentine’s Day things can go only one of two ways: very wrong, or very, very right. You can end up in the proverbial doghouse, which is pretty much the least chic/least cute place to be, or you can end up in the palace of love: a place that’s not an actual palace (sorry!) but a love nest where a bunch of love and a lot of more than love goes down.

And though this historic, romantic, chocolate-induced, Hallmark-driven day of love (also known as the one day of the year you’re guaranteed to not only disappoint but also get in a fight with your significant other) is meant to be one where we bask in the company and cuddles and affection of another who has our heart, and body and…ok I’ll stop there, it’s also become a day that – if not strategically planned, and if expectations aren’t discussed - can add a shitton of pressure, a whole lotta disappointment, and an opportunity for us to be cut from our love’s life once and for all. (As an aside: Feb 14th marks one of the busiest days of the years for couples to break up. I know. Gulp.)

As a relationship columnist who gets material by going on dates across the country, and by coaching couples who do just that, I’ve had my fair share of Valentine’s Day disaster stories (T-Swift, need a ghostwriter, girl?) and Valentine’s day highlight reels (I’ll save those for my book). And so, I thought I’d fill you in on where to go and what to do depending on which stage of the relationship you’re in.

Underground couple

If you’re single and on the hunt
Whatever your end game is, chances are you'll find something to suit your needs and wants by downloading happn. It's the only geo-location based dating app that matches people that actually pass you and are in your immediate vicinity (within 250 meters.) The free dating app is based on the premise that it’s your second chance at a missed connection. All you gotta do is download the app on your phone and just do you. If you go into the app, the people you’ve most recently passed pop up on your screen and you have the option to either click a heart, or an x. If you click the heart, and they do as well, you guys connect in a mutual window where you can share and send private messages to one another. Hole up on the Sky Yard or in the lounge with your besties and grab a cocktail (may I suggest TKTKT?) before checking out who’s around. What I love about this app is that you avoid the rejection that comes with approaching someone at a bar you’re at, only to find out they’re in a relationship or don’t swing your way. The app clears the pressure.

If you met on a dating app a couple weeks ago
You know it’s Valentine’s. They know it’s Valentines Day. And though you have yet to discuss the day, it’s almost weirder when you fail to acknowledge it. This early on, it can be a make it or break it moment. Whether you just want to hook up, or perhaps see a future down the road, now's the time to make a sweet gesture, but do so in a way that is affordable, playful and doesn’t put pressure on either one of you. My suggestion? The Drake’s Valentine’s Day Comedy Underground show.

No Vacancy

If you’ve been hooking up all year but don’t have a title but want one
This is simple, book a flirty Pillow Fight Package at the Hotel or The Drake Devonshire Inn, which includes a Pleasure Menu gift from Come as You Are (Available until Feb. 28, 2017). It shows that you’re willing to not only make a financial investment, but also an investment in your time, and the alone time out of one of your abodes will allow you to feel the luxury as if you’re on vacay, while sussing out whether or not you want to make something more serious about the situation. And hey, if it goes well, it’s the perfect backdrop to have "The Talk".

Your bae for days
Romantic gestures are totally wanted and encouraged, and won’t be misconstrued with someone you’ve been with for a while. Head over to The Toronto Flower Market at the Hotel and at Drake One Fifty with your love, and allow them to pick out their fave bouquet. Want to surprise them? The helpful florists can tell you what to choose if you let them know your other half's personality. It’s sweet. It’s romantic. And you’ll win extra points for doing something unexpected. Cliché though it might be, there’s nothing sweeter than being gifted with a bouquet on the international day-o-love.


If you’re married or want to be v. soon
Valentine’s Day dinner at the Hotel, Drake One Fifty, + Drake Devonshire. Each venue offers great Valentine’s Day menus, a cozy yet sexy ambiance, and dim lighting and delicious music to help set the tone and spice things up, as if you need it!

A last tip for you lustful, little, lovebugs: Hit up the photo booth at any of The Drake properties while you’re on site. It’s a great way to get a private moment (before you click the flash button) and a sweet forget-me-not to commemorate your time together, whether it lasts for many days here on in, or whether you get dumped that night.

Oh and if you want some privacy if you tend to fall down that PDA rabbit hole? There’s a lot of cozy nooks on each floor at The Drake Hotel to have your privacy. Bon appetite and, shall I say, bottoms up?!

Photo booth

Jen Kirsch is a relationship columnist and dating expert. Want to thank her for winning you your V-Day? She's registered at The Drake General Store! ;) or you can just follow her on twitter, @jen_kirsch.

Posted in: Hotel + Travel

Tags: Comedy Underground  Toronto Flower Market  Valentine's Day