By With February beginning, we all know what that means: Valentine’s Day. And with this holiday comes something we all dread—the memories we try to forget. I’m talking about those awkward first dates, embarrassing moments with your crush, or the hangout that just didn’t go as planned. Now, maybe I’m just cynical, but I’m sure I’m not alone here. For some people, Valentine’s Day can be a total drag. Of course, if you’re one of the lucky ones who absolutely loves it, I’m genuinely happy for you. But let’s face it, not all of us are that fortunate. With all this in mind, I’ve decided to give you my two cents on first dates—specifically what to do and what not to do—to hopefully spare you from adding another cringe-worthy memory to your love life.
Best First Date:
A walk is always my first thought with first date ideas, especially in Helena. A long walk downtown in the walking mall or even a hike on Mount Helena is an amazing way to get to know someone. One, it’s free, and two it doesn’t involve eating or anything that could evoke potentially embarrassing moments. You get some exercise and you get to know someone, what could be better?
Worst First Date:
Obviously, this could be up for debate, but the movie theater is an immediate no-go. You basically have no time to talk and the whole time you’re watching the movie, you are just overthinking everything and wondering what they are thinking.
A close runner-up would definitely be a sit-down dinner, it just feels awkward and like you’re trapped in silence.
Best Coffee Date Spot:
The Merc is a go-to coffee date setup. The knick-knacks are the perfect conversation starters and allow you to walk around and just feel out the energy. They have amazing coffee, as well as other teas and chai of sorts. It’s more of a community space than a coffee shop, and computers actually aren’t allowed. It’s meant to be a place to spark conversation and do mindful things. They’re cozy seating options that are absolutely perfect to cozy up in and chat.
Best Dinner Spot:
Dinner is a big one, but I’m here to give my two cents. If you’re 21+, On Broadway is an absolute staple for date night. They have an extensive drink menu with so many options. You wait in a comfortable area, where you can get appetizers and drinks before you head to the main dining room. The lighting is low and the energy is amazing, it’s perfect for a late-night chat over some pasta.
If you need a cheaper and maybe more chill spot, the Old Salt Outpost is burger heaven. Take it to go for some comfort food at home or sit and enjoy the bar energy while catching up. Old Salt uses Montana-raised beef so by supporting them, you are supporting your community which is always a huge plus.
Best Activity Date Spot:
It’s cold out and that’s for sure, but let’s say you both like to get after it. Skiing or snowboarding is a super fun date activity. Get some exercise in, chat on the lift, and enjoy some warm food at the lodge while spending time together. If you aren’t comfortable with the mountain, there are a few local ice rinks you can visit to test out your ice skating ability this winter. While it may end up with a few spills here and there, it is definitely worth the bonding moment.
If you’re looking for an activity that doesn’t involve the risk of falling, take a stroll downtown to visit The Painted Pot. It’s the perfect spot for creative minds to unwind and make something special. Not only does it spark conversation, but it also gives you the chance to enjoy some quiet time together while chatting. They’re open most days and offer a wide variety of options to choose from.
Take my advice or don’t, but trust me when I say this is expert-level guidance—I’ve seen it all. And nothing, nothing could be worse than one of my first dates being on Valentine’s Day.
I was excited, nervous, and a mix of everything in between when my high school crush decided it would be a great idea to go four-wheeling at night in the snow. Of course, my gut told me it was a terrible idea, but when you’re head over heels, what do you do? Lesson learned, let me tell you. We ended up tipping over, and yes, I did, in fact, see my life flash before my eyes.
But hey, I live to tell the tale.
Pro tip: Never, ever get on a four-wheeler for a first date, no matter how cute the high school football player is. Trust me, there are better fish in the sea.
