We’re always looking for fun, easy ideas for winter date nights, simple ways to make a Friday or Saturday night feel more festive. I’m not always in the mood to hit a restaurant…either it’s too cold, we’re too tired (a pitch-dark 5PM always feels like midnight to me), or the kids are feeling grumpy about it (restaurants are hit or miss with them). So instead, we’ll look for creative ways to make everyday adventures feel a little extra-special.
5 Cute Winter Date Ideas (Think: Couples, Family Fun Night Or Valentine’s Day)
These five ideas are the ones we turn to the most often, and they can be executed with or without the kids. Because they avoid the traditional romantic restaurant scene, these ideas are our usual moves for Valentine’s Day celebrations, too. Festive, fun and easy.
For a little glimpse of what I’m talking about, give our winter date night video a watch. Below I’ve gone into a little more detail about each date, as well as linked up the pieces featured in the video (if interested).
Date Idea 1: Chocolates & Champagne At Home

I’m embarrassed by how often we do this. I mean, it’s not every weekend…but…well. It’s close. That said, it’s kind of amazing how a Saturday night can feel extra-special when opening a fancy box of chocolates to the little “pop!” of a champagne cork. (Wandering around and picking out special chocolates and bubbly is one heck of a fun, themed walk for a Saturday afternoon, too.)
Date Night Outfit Pieces
Date Idea 2: Ice Skate, But With Après
The après scene doesn’t have to be just for skiing! Many outdoor city rinks have some sort of après, but if not, bring thermoses of hot cocoa (spiked or not), or hot apple cider and/or mulled wine. This would even be fun at a sledding hill, to be honest (and I’d bring our Rumpl stash mat for that).
While we most often take the kids with us when we go ice skating…Mike and I recently snuck over by ourselves. The kids had ski practice, but the conditions were too icy for me, soooo…ice skating? Mike and I ended up having a blast, just the two of us. It served as a good reminder that changing it up a bit makes for a pretty memorable day. I forget, sometimes, that even adults need to play.
Ice Skating Outfit Pieces
Date Idea 3: Go Skiing, But Eat At The Fancy Lodge

We almost always pack our own lunches when we ski (lodge prices are ridiculously high, and one can only eat so much chili and fries) but the occasional lunch splurge makes a day of skiing feel like a date. Whether it’s the fancy lunch at the top of the gondola, or having a beer in the hilltop bar…it makes our usual skiing day a little extra special.
Sidenote: Last year, only Pax trained on Fridays, so Raines skied with Mike and I. We almost always did a little happy hour situation in the hilltop bar (Raines had hot cocoa, of course), and he later remarked that sitting outside with us, with his drink and the view, was one of his favorite things about last winter. It’s deceptively fun.
Ski Lodge Outfit Pieces
Date Idea 4: Have A Bougie Bonfire
The name, ‘bougie bonfire’ is a joke, of course. But there’s something extra-special about layering up, adding blankets, and cuddling around an outdoor fire in the winter. You can make the snacks as bougie as you want (or not at all). We swear by our Solo stove (although, I don’t think the smaller size works nearly as well, which is annoying) as well as Rumpl blankets. They’re lightweight, portable and warm* — we bring ours everywhere.
*It was, like, 5 degrees (F) when we shot this, and Rumpl blankets are NOT warm enough for that type of cold. Twenty degrees warmer and I would’ve been fine. But let’s all appreciate my sacrifice for the aesthetic, haha.
Bougie Bonfire Outfit Pieces & Supplies
Date Idea 5: Shoot Some Pool
Instead of sitting down for a nice dinner, my boys are always MUCH more willing to hang at a bar and play some pool. This weekend “tradition” of ours started years ago, when a fun crew of 20-somethings taught my boys how to play at Sunshine (a ski resort near Banff). It was fun when they were small, and now that they’re older and getting pretty good, it’s even better.
Sidenote: While shooting this video, we all played the worst game of pool of our lives. And while I’m pretty impervious to strange looks at this point…having folks watch us PLAY TERRIBLY WHILE FILMING was a new, embarrassing low. 🙂
Another side note: I do love to dress up a little on a Friday night, even if we’re just heading out to play pool. That said, the bodysuit I’m wearing in the video was a mistake for pool playing. Whenever I bent over…yikes. It’s great for everything else, though.
Pool Night Outfit Pieces
That’s it!! I’m always on the hunt for fun ideas, so if you have any good ones, please share!!
xo,
S