Travel Blog

3 Nov

First Impressions Count: Ideas for Fall First Dates in Whistler

TAG: Arts Culture, How-To

Posted by: Nikkey Ward

Guest Author: Brian Hockenstein

Winter is fast approaching and for those of us who find themselves single it’s often the time of year we start thinking of finding that special someone to share those powder days and lazy morning with. Summertime is for fun times in the sun with your squad but there’s really nothing better than having someone to share the magic of winter with, and to share breakfast with before hitting the slopes! Meeting people in the Sea-to-Sky has never been a major issue – the social scene is alive and well – but sometimes it can be hard to pick an activity for that ever important first date. In order to help you with that task, I’ve selflessly flung myself into the Whistler dating scene and hit the pavement to find out what the best first date activities are. It’s a tough job but someone’s gotta do it!

Couple Walking the Valley TrailCHAD CHOMLACK PHOTO

These five first date activities are tried, tested and true. If they don’t work a charm you’ve got no one to blame but yourself … luckily that next first date is just a swipe away!

1. The Fancy Dinner Date

One of the best thing about people from British Columbia is how generally laid back and chilled out they are, but don’t be fooled – there’s not a woman alive who doesn’t appreciate being taken out on the town to a fancy restaurant and being shown a proper old-fashioned good time. Use the occasion as an excuse to get a bit dressed up and show her your classy side. Open the door for her, let her order first, flex those conversation muscles and show her that chivalry is not dead. Making this even easier for you is the fact that many of the best restaurants in town have out of this world specials all fall where you can sample some of the finest dining in the world for a price that won’t break the bank. Flip through the Pique, all the deals are in there.

My personal fave – and the one I oh-so-generously checked out for this article – is the Rimrock Cafe. It’s laidback atmosphere is as pretentious-free as it comes but the food there is some of the best in a town already known as a foodie’s mecca. $50 gets you a three course meal that would cost well over $100 any other time of the year. (Editor’s Note: Brian made a fine choice here. The Rimrock Cafe has just been nominated #2 Fine Dining Restaurant in Canada by TripAdvisor. Bonus points!

Fine Dining in WhistlerMIKE CRANE PHOTO

2. The Lounge Date

Whistler is known for its clubs and party scene but take it from someone who knows, you absolutely DO NOT want to head to an underground nightclub on a first date. There’s just too many variables at play down there, trust me! Alternatively, the lounges and hotel bars around town are absolutely perfect for getting to know someone. There’s the ever important alcohol to take the edge off things (drink responsibly though) and the atmosphere in most of these places is perfectly conducive to a nice, deep, get-to-know-you conversation. If there’s a lull in the conversation, you can play a bit of people-watching and better yet, if you’re smart and take her to a place where one of your buddies are working behind the bar, you get to impress her with that ever-important local status. “Oh hey there Dave, I totally forgot you work here. Two free cocktails? Don’t mind if I do”. You get my drift.

There’s a ton of sweet lounges around town but if you’re looking to go high-class head to The Mallard Lounge in the Fairmont Chateau Whistler. Looking for something a bit more casual? The Attic at 21 Steps is the place to be. Tell Dave I sent you.


3. The Dog Walk Date

This is my personal go-to. I haven’t met a woman yet who doesn’t love the idea of taking a walk in the forest with a dog. There’s a few reasons this is a killer idea. First off, it’s basically just an excuse to go for a walk in the woods and who doesn’t love that?! Rain or shine, the coastal rainforests Whistler is carved out of are simply magical. Secondly, it shows your responsible side. For those of you who haven’t taken the step into pet ownership, fear not. No doubt you know someone who has and would be more than happy to lend your their furry friend – it’s a win-win as you get a date out of it and they get their pet some exercise without having to actually do anything. Best part of this killer date idea? It’s 100% free!

Where you go is up to you but to get you started I’d personally suggest the Cheakamus River trails near the Cheakamus Crossing neighbourhood. The trails are mellow, easy to follow and you can spend as little as 30 minutes or as long as two hours exploring the forest and river.

Photo Courtesy Brian Hockenstein

4. The Sporty Date

Whistler, and BC in general, is full of some of the top athletes in the world. There’s a good chance your server last night is a professional skier and an even better chance that person you just asked out on a date loves nothing more than getting muddy while biking or going for a run. If you guys share a common sport, heading out on the trails is a great way to spend a day together. Sure, it’s hard to keep a conversation up while hoofing it up-hill for half an hour and sweating your brains out but once you get up there, take a seat, pull a couple of choice snacks and a mini bottle of wine out of your pack and bam – instant picnic!

There’s a big caveat here. There’s a good chance that petite innocent looking girl you met at the bus stop can – and will – absolutely crush you on the trail. Keep that ego in check and don’t get all pouty-face when she nails that drop you just chickened out of. Nothing is sexier than a man who isn’t afraid to be shown up by a girl.


5. The Hiking/Activity Date

As the snow slowly creeps its way down the mountains there’s no better way to enjoy the beautiful fall season than hitting one of the plethora of hiking trails around town. From super mellow hikes at Lost Lake for the inexperienced, to sweat-you-shirt-see-through hikes like Wedgemount Lake, stretching those legs and getting out in nature is one of the best ways to create a bond between two people. Do a bit of research though and make sure you know what you’re getting into – there’s no quicker way to get the ol’ eye roll than pretending you know what you’re doing only to have it all end in getting lost in the woods. As an added bonus, at this time of year sooner or later you are more likely than not to hit the snowline, and you know what that means. . . Snowball fight!

Local’s tip: The still fresh Skywalk Trail isn’t for the faint of heart but will get you up into the amazing alpine of Rainbow Mountain under some huge hanging glaciers that are sure to take your – and hopefully her – breath away. And for something a bit easier on the legs head to the newly revamped Train Wreck hike. There’s a brand new suspension bridge that makes access a snap and the trails to, and around, this interesting site are absolutely gorgeous.


So there you have it. Five perfect first dates for you and that special someone. The only thing I’ll add is that if any of these get you the ever elusive second date – you owe me a beer!

Ladies Choice

By Pip Campbell

While I’m sure the ladies will all agree that a little chivalry goes a long way, we’re also up to plan a few first dates of our own. I’m here to level the playing field with a few choices from the ladies side and since we welcome equality and diversity here in Whistler feel free to throw the traditional guy-girl choices out the door and choose what works for you. Happy dating!

  1. Hiking/Biking/Skiing/Boarding – Brian has this one absolutely right. An active first date is a fun first date and if you keep your eyes off your phone on the chairlifts this winter you might even find love between laps. Hello, new adventure buddy. Shall we après?
  2. Coffee, Tea Sweet Treats – Keep it low key and cozy. Head to a warm spot like Mt Currie Coffee or the Whistler Tea House, grab a warm drink and have a chat. Their choice of sweet or savoury treat might just give you a little window into their mind – what if they pick the salted caramel bar? Lemon meringue? Abstains from sugar completely? Food for thought.
  3. Cocktails – Should you desire a partner who knows their single malt from their Malibu, grabbing a cocktail with them will separate the wheat from the chaff, as well as being an excuse to dress a touch above ‘mountain casual’. Try Bar Oso, Alta Bistro or the Cure Lounge at Nita Lake Lodge for beverages that ramp up the class.
  4. Cultural Outing – combine one or more of the above with a trip to one of Whistler’s museums or art galleries if you want to find out if they have brains as well as brawn and aren’t afraid to hold an intelligent conversation.
  5. Event Date Night – Whistler’s got a ton of events happening year round, making for built-in entertainment. Top picks for a Whistler date night in coming months are the food and drink fest, Cornucopia and the Whistler Film Festival.
  6. Dancing – Brian and I diverge slightly on this one. If the evening is going well, consider taking that next step and hitting the dancefloor. Not ready for underground? Fair play. Check out the GLC for a rad selection of DJs and Hip Hop nights or Brandy’s for a little bit of funk.
  7. Toque shopping – as Feet Banks once said ‘a toque is an extension of your personality, so select wisely’. In the simple act of strolling the Village and picking out a new head warming garment, you just might get a glimpse into what makes them tick.


Not sure what it is about the mountains, but they’re a pretty special place for dates, proposals and weddings. If all goes well and you need to *ahem* get a room – can sort you out.

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