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5 Of The Worst Outdoor Dates You Can Imagine

Author: Brooke Hess

October 08, 2019

In the era of online dating, it has become increasingly easy to find and go on dates. Before even meeting a person, you have access to all their info. You know their name, age, gender, hobbies, profession, favorite food, relationship history, religious preference … so with all that information, dating should be easy, right?

Well… maybe not for everyone. And by everyone, I mean me. I have had some horrendously awful first dates in the past few years. So bad, in fact, that I decided to write them down, and then ask my friends if they had any good (bad) first date stories. Turns out, I am not the only outdoor enthusiast struggling with the online dating game. But at least we ended up with some good stories—right?

All stories are written in first person from the storyteller’s perspective, but all names have been removed to ensure anonymity for all parties involved.

Not Your Babysitter

I went on a Tinder date with this surfer dude. I picked him up because he didn’t have a car or even a license. This should have been red flag number one, but at 18 years old, I didn’t think much of it.

We planned to go surfing. I didn’t own a board, but he told me he would figure it out for me. He put his surfboard and wetsuit in the back of my car and we headed to the beach. I parked the car and asked about the board for me and he said, “Well I thought it would be cool if you just watched me surf for awhile.”

If a date said this to me today, I would leave immediately. But, like I said, I was 18 years old. New to the dating scene and not much confidence. I watched him surf for two and a half hours while he failed to catch every wave. Just as I was about to drive him home and end the “date,” he offered to make me dinner.

“OK, maybe he will redeem himself,” I thought. He then lit up a bowl without asking if I was okay with him smoking weed in my car. (I was not, by the way.)

His big talk of a fancy dinner turned into spaghetti with premade sauce. Again, 18 years old, so spaghetti didn’t seem so bad. And just when I thought the date was starting to turn around, he started to cry. I wasn’t really sure how to respond when he sat down in my lap and blubbered, “Sorry, I took a hit of acid earlier today and I guess it is hitting me way harder than I thought it would.”

He then puked on my floor, watched as I cleaned it up, and asked me for a ride home.

A Case Of Mistaken Climber Identity

I went on a Tinder date and was immediately smitten with this individual. She was very attractive, and really into climbing. Almost to the point of being obsessive.

I think she thought I was someone else, though, because she definitely thought I was a crusher. Now, I like climbing—I can lead moderate sport routes and easy trad. But I am not a super hardcore, super strong climber. Maybe I have a doppelganger who’s a much more advanced climber than I am, and she was confusing me with him.

She kept bringing up climbers who I would have known if I was really hardcore, and I would respond with, “Uhhh, I don’t really know who that person is.”

I thought the date was going well otherwise, so we started talking about going on a climb together. But when we got down to the nitty gritty about how hard we climbed, she seemed unhappy with me. We were discussing a route to potentially climb together when I expressed hesitation about leading the crux pitch.

“Sorry, but I’m just not quite comfortable leading a multi-pitch 5.9R trad route yet.”

As soon as I said this, the date was over.

“What the f*ck,” was the last thing she said to me, and I never heard from her again.

Hopefully she has found my doppelganger and gone on a date with HIM instead!

All Talk And No Game

Driving to the ski resort together, all I hear is talk of this guy’s dream ski lines. “I can’t wait to get on some massive backcountry lines this season,” my date says. “I have a huge goal of making it up to Alaska this spring to hit up some spines.”

I grew up skiing. My parents had me on skis before I could walk, I was skiing double black diamonds by the time I was eight, and was skipping school for powder days by high school. I love skiing and am fairly competent at it. But I know my limits, and know that steep spines in Alaska probably aren’t on my checklist. This guy, apparently, is on another level. My only impression of him is that he loves to ski. And he is f*cking good at it too, apparently.

We’re gearing up for an early-season skin up and down a chill resort run before the resort opens. My date finishes buckling his boots, grabs one of my skis, and starts putting my skin on it for me.

“Oh, I got it,” I say. “Thanks, though!”

Skinning up the first few hundred meters, we stick together as a pair. Discussing favorite ski lines, climbing goals and plans for grad school. We approach a steep section, and my date suddenly announces, “Cool, well if you don’t mind, I’d like to get a good workout in today, so I’m gonna hustle on ahead. I’ll see you at the top!” And he takes off.

I spend the next hour and a half skinning a quarter mile behind my date. No talking, no laughing, no flirting. Just me left in the dust feeling like I wasn’t fast enough or good enough to keep up.

When I reach the top of the run, I find my date sitting in the snow fiddling with his helmet. At first, I can’t see what he’s doing, but then I realize that he’s attaching a GoPro to his helmet. “I don’t want to miss any sick lines,” he explains.

On the ski resort. On a blue square. In November.

As soon as our skins are off, helmets on and ski mode engaged, my date takes off. “See if you can follow my turns,” he yells over his shoulder as he zips off.

Feeling a fire burning inside me as a man I have never skied with offers me guidance down an easy hill, I am motivated to prove myself. Turns out, it wasn’t that hard.

It takes me no longer than 20 seconds to catch up to my date. His primary method of ski turn is the pizza technique. Flying down the hill completely out of control, his skis never quite reach parallel. Complete pizza formation, or floppy and far apart is all I see. At first, I linger behind him unsure whether to pass and enjoy my own turns, or to stay behind and make sure he gets down in one piece. I choose the former, and enjoy some early-season powder turns down to the parking lot.

We meet up back at the car and enjoy a wonderfully awkward drive home. Lesson learned: If he has a photo on his Tinder account of a guy skiing a massive couloir in Wyoming, it isn’t necessarily him!

S.T.Don’t!

Walking back to the truck after a wonderful hike near Mt. Adams, I could tell the date was going well. This guy had good vibes, a wonderful personality, and the body of a Greek god.

We hopped into the truck with a plan to get groceries, then head out again for a picnic under the sunset. Mid-drive, my date turns to me and says, “Hey, so I need to tell you something that might be really awkward since this is our first date… but I have been having severe pain in my right testicle for the past hour and a half, and it is slowly getting worse.”

“Okay… yes that is awkward. But thanks for telling me! Should I take you to the hospital?” I responded.

We decided to wait it out and see if it got worse.

Fifteen minutes later, in the chip aisle, he froze up with a pained look in his eyes.

The emergency room staff was quick to put him into a gown and get him in his own private room. We were both joking around about our first date ending up in the ER when the doctor walked in to examine him. I ushered myself behind the privacy curtain, this being the first date, and waited for the doctor to finish. 

Still in the room, but protected by the privacy curtain, I could hear the doctor: “Well, it doesn’t look like there is any testicular torsion to worry about, so just based on your demographic, I’m going to say this is a classic case of Gonorrhea or Chlamydia. We’ll get you started on some antibiotics straight away and it should be cleared up within a week.”

Needless to say, neither of us got lucky that night.

Communication Junkshow

I met this girl on Tinder. We had hung out a few times and I could tell we were really different, but we had fun when we first met, so we decided to go on a weekend trip to Glacier National Park. I guess I didn’t specify what type of trip it was going to be because she showed up in fancy clothes, like we were going downtown. The entire drive, she kept putting on makeup and foundation, and it dawned on me that maybe we weren’t on the same page. In my mind, we were going to be hiking long days, sleeping in the back of my truck, and not taking showers. In her mind, we were on a fancy weekend getaway.

The trip quickly crashed and burned. The 16-mile hike turned disastrous when her boat shoes—the only shoes she brought–gave her heinous blisters and sore spots. The romantic picnic on my truck tailgate turned into a parking lot mosquito massacre. And all the nice food we brought for a fancy dinner turned into mush in the wet and soggy cooler.

Eventually, my date told me straight up that she was having a horrible time, which was perhaps the first real form of honest communication we had shared. She told me it was a shitshow of a trip. Which it was.

I think I had forced my idea of a rugged, backcountry trip, and hadn’t been very receptive to the fact that maybe it wasn’t what she wanted. I mean, she hadn’t even brought a backpack. I’d just loaned her my extra one and said, “Sweet, let’s go hike 16 miles!”

She wasn’t happy. It was very clear that we were not going to see each other after that.

Brooke Hess

Growing up in Missoula, MT, Brooke was on skis before she could walk, in a climbing harness before she could read, and in a kayak before she could drive. A former U.S. Freestyle Kayak Team member, she spends the majority of each year living in her truck, traveling from river to river in search of the world’s biggest and best waves. A degree in geoscience, plus a lifetime spent pursuing outdoor sports, has led her to a career chasing writing opportunities focusing on conservation, feminism, and outdoor recreation.