I Tried Outside-The-Box Activities On First Dates & This Is What Happened

Illustrated by XAVIERA ALTENA.
Refinery29 is teaming up with The Laughing Cow for an #AntiRoutine mission that's all about shifting your perspective to unlock new possibilities. Say goodbye to your monotonous routine and instead, make the choice to switch it up with simple lifestyle changes that will garner lasting, positive effects. Ahead, one writer takes on the challenge.
When it comes to dating, most of us are guilty of succumbing to a boring first-date routine — no matter whether we’re Tinder devotees or anti apps entirely. We rely on the same go-to bars and restaurants that, while comfortable and familiar, inevitably lead to the same stifled getting-to-know-you conversation date after date.
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So when my friend recently caught me yawning at her roster of wine-bar dates lined up for the week, she asked me how I would switch things up while getting to know a complete stranger.
I’ve dealt with plenty of adventurous situations in my life, from devouring live octopus in Korea to trekking through the Sahara on a camel. But when we're talking first dates, departing from the ordinary is arguably just as risky; there’s so much room for judgment and discomfort in suggesting ideas to a stranger that many would consider inappropriate or flat-out weird. That said, trying something unexpected for a first meet also has the potential to bring people closer together — or, at the very least, keep them far more entertained.
So I decided to challenge myself: For one week, I’d skip my go-to first-date locales and only suggest completely atypical activities. To make things even riskier (and more enlightening!), I also planned to ask each suitor to reflect on our experience. Here's what I learned.
Illustrated by XAVIERA ALTENA.
Date #1: Apartment Hunting
While it usually takes a year or more to work up to apartment hunting with a significant other, for me and Y*, it took exactly three minutes in the wine aisle at the grocery store.
Y and I bonded over an Argentinian Malbec, which led to a conversation about the best patio bars to sip red in our neighborhood. After he smoothly proposed that we check one out together, I bravely one-upped him and asked if he’d first like to check out apartments in the area. Casually confident or insanely creepy? Surprisingly, he laughed and said it sounded like quite the interesting proposal.
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So for our first date, we met and toured four separate apartments in the city. There we were, complete strangers, hit smack dab in the face with kitchen-backsplash-tile and floor-to-ceiling-window options. Who needs second drinks when you’ve got second bedrooms to plan for? Apartment hunting took visualizing a possible life together to a new level — insanely quickly. Above all, it kept us on our feet and far away from typical first-date distractions like food, drinks, and a crowded venue.
From fantasy-like downtown condos to renewed urban lofts, we floated between rooms, noting what we liked and didn’t like about each space. Between our eerily similar taste in design aesthetics (Exposed concrete beams? Yes.) and Y’s cool confidence in taking on such a unique activity, apartment hunting ended up actually being a fun activity for the both of us.
"I couldn’t fall back on any of my old tactics or 'moves' because they didn’t fit the date," Y told me afterwards. "I had to be present with the situation and my feelings to figure out what to do." It was a sentiment I echoed. Plus, who doesn’t love playing house with someone you’re into? Rationalizing preferences for a deep-set farmhouse sink is arguably sexy.
Illustrated by XAVIERA ALTENA.
Date #2: Road Trip
Ahh, the couples trip. Traveling with a significant other, while glamorous and entertaining in theory (and on Instagram), often serves as a serious make-or-break point between two people. For me personally, it’s a huge sign of compatibility, which is why I like to dive into it early in the process of getting to know someone — whether it’s a friend or a romantic interest.
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So when C* asked me out on a first date, I broke out my list of new spots I’d been dying to check out in Asheville, NC (about two hours away by car) and asked if he wanted to explore all seven of them together for our first date. No pressure.
Our day started early on the road, where we bonded over favorite music and gas-station snacks. Once we reached Asheville, that connection continued in what would become a 12-hour-long first date (possibly a world record?).

Our moments of silence were relaxed, not stiff and awkward like they would be while sitting at a bar.

I’m definitely a foodie and a planner, and C was very comfortable letting me take the reins on our excursion of restaurants, breweries, and hidden gems. Even though we’d just met, wandering through town together felt effortless; our moments of silence were relaxed, not stiff and awkward like they would be while sitting at a bar.
C was down for anything and carried an energetic, adventurous personality that made what would be a daunting first date for most a total breeze. I felt like I’d hit the road-trip-partner jackpot. From food-coma levels of pizza eating to impromptu pinball tournaments, it seemed like we couldn’t stop laughing and enjoying ourselves. Or was it just me, easily buzzing along, spending a day doing something I already inherently enjoy as a traveler?
Here’s what C had to say: "Right from the start, your energy helped make me feel like the vibe overall was chill and easy. It was not a high-strung first few moments of hand-wringing and awkward icebreakers — the conversation just seemed to blossom. It was also fun singing in the car to songs we both knew and were hype on. We could just enjoy the revelry of being silly together, all guards down.
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"A trip together on a first date feels like a rare and special intersection to me, and I don't think it can happen very often, nor do I expect it to. It takes an alignment of interest and place in life to be able to flow like that. It felt like we were just riding a wave together, having spent the whole day connecting on so many levels."
Illustrated by XAVIERA ALTENA.
Date #3: Silent Disco All-Nighter In An Art Museum
When I heard there was a silent disco happening at a nearby art museum, followed by an event spanning from midnight to 6 a.m. with acrobatic performances, tarot-card readings, an infinity room, and — most importantly — an infinite amount of free doughnuts, I knew I’d struck gold with my Saturday-night plans. While I’m no stranger to a solo stroll at an art museum, this felt like an opportunity to share a meaningful experience with a date. Besides, I really needed someone to show off my new glow-in-the-dark wolf shirt to.
Luckily, my date for the evening, J*, was just as into wolves and art as I was. As soon as we entered the museum, put on our neon-lit headphones for the silent disco, and took in the magnificent amount of interactive displays in the gallery, it was clear this was not going to be an ordinary date experience for either of us.
Being in an environment full of beautiful artwork, light shows, and captivating entertainment naturally led to far more imaginative conversations than most day-to-day scenarios, much less typical first dates.
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Having built-in activities on the itinerary eliminated any chance of friction in deciding what to do next.

Having built-in activities on the itinerary also completely eliminated any chance of friction in deciding what to do next. Sure, we had trouble squeezing in the conventional questions about each other’s lives and backgrounds between dancing and looking at art, but this was a problem I thoroughly welcomed in breaking routine.
When I asked him for his thoughts afterwards, J told me, "The art museum encouraged creative attire for the event. You choosing a glow-in-the-dark howling-wolf shirt told me everything I needed to know about your self-confidence.
"There’s something about being surrounded by art that makes you look beyond what’s just in front of you, which epitomizes what a date is supposed to mean. It let me focus on your themes as a person, instead of specific life details, which often mislead…especially if you’re a hopeless romantic like myself."
As it turned out, staying true to my outside-the-box first-date ambitions, despite some initial discomfort in the beginning, paid off and restored my faith in finding fellow thrill seekers. My weeklong journey in outlandish dates reached its peak with date number three. My night at the museum with J wasn’t a cult-classic romantic comedy, rather the bold and exhilarating first date I’d been dreaming of, overflowing with the kind of creativity I’d want any of my routine-ridden friends to stir up on their next dating adventure.
*Names have been changed.
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