Worst. Date. Ever.

By Ben Olson
Reader Staff

Usually when Valentine’s Day draws near, we take time to show our significant others how much they mean to us. This year, though, I can’t help but remember the worst first date in my life.

Years before I met the love of my life, I was working at Hidden Lakes Golf Resort as a golf professional. I had worked at Hidden Lakes every summer since I was 15 years old and worked my way up from a kid washing golf carts to teaching golf lessons and manning the pro shop.

Most lessons that I taught were either to older golfers who wanted to shave a few strokes off their score or juniors who hadn’t swung a club before.

One day, to my surprise, my student was neither. Rather, a beautiful blue-eyed woman appeared with a set of clubs and I felt my heart flutter. We’ll call her Annie.

To say I was smitten with Annie is putting it lightly. She was easy to talk to and had a smile that could launch a thousand ships. I gazed at her like a puppy.

I was only 21 at the time, filled with the baseless confidence we seem to have at that age. I walked her to her car after the lesson and, suddenly, before I knew what was coming out of my mouth, asked if she ever wanted to go “get a drink or something.” I didn’t often ask people out cold like that, but I was encouraged by her secret smile throughout the lesson.

Her forehead wrinkled and she smiled again, but shook her head and told me she wasn’t really interested in dating anyone. She was gracious about it, and let me down like the pup I was.

I could have been humble and accepted defeat, but I pushed the issue, asking in my faux smooth way if we could see each other sometime.

“You know, your zipper is down,” she said, pointing to my khakis. I looked down and saw, to my horror, my fly was indeed down and a bit of my polo golf shirt tail sticking out for all to see.

She got into her car right when I realized the zipper must’ve been down for the entire 40-minute lesson. She drove away as I stood there blushing like an idiot.

About a week later, I mustered my courage and called her. I asked her again if she’d like to hang out. I said we could go out on the boat, have dinner at Bottle Bay. This time, to my surprise, she said, “Sure,” and I hung up feeling like I had landed a double backflip.

The day of the date came around and I was well prepared. I shined up the boat and filled it with gas, then picked her up in Hope for our “date.” We motored around for an hour or so, stopping to drink some beers and share stories about our lives. The more we talked, the more I grew smitten with her. I learned she was 10 years older than me and had a professional job that put her way out of my league. Maybe it was my unfounded confidence, or that first lesson when my zipper was down that amused her, but I got the feeling she might like me, too.

We then drove the boat over to Bottle Bay for dinner. While idling into the visitor dock, the beers swimming in my head, she asked if I could explain how to dock a boat. With a pompous air, I went through the motions of boat angles and throttle positions, then, when just about perfect, I said, “Now, when you’re in position, just tap the throttle in reverse and…” 

I lost my footing and landed with my hand on the throttle, pinning it all the way forward. The boat lunged ahead, the bow rising in the air. It went up and over the dock, teetering carefully on its hull for a moment before groaning back down into the slip. It landed like the sound of failure. I scrambled off the boat and tied off as fast as possible, head down and red-faced again. Again, Annie was gracious. She only laughed at our little misadventure and deftly stepped onto the dock with a, “Well that was interesting,” kind of whistle.

We walked up to the restaurant and I heard a round of applause coming from the dining deck. Looking up, I realized with even more shame that the entire restaurant had watched me crash the boat onto the dock and they were now clapping at my nautical “mastery.” I replied with my head down, hand in the air to acknowledge my status as an idiot.

Undaunted, I led the way to the bar, where I saw a dog lying there sleeping. I bent down and said something goofy, patting him on the head, but the pooch suddenly sprang up, yelped and ran from me at top speed down the beach. His forlorn yelping could be heard across the bay.

“What the hell did you do that for?” the bartender yelled at me, running after the dog. “He has issues, you know.”

“Sorry!” I called after him. On cue, every head from the applause section of the dining room turned and looked at me, first the boat crasher now somehow abusing some poor dog. Their disdain for me was as thick as their porterhouse steaks.

“Boy, you’re really on a roll,” Annie said, with another laugh. She seemed to be enjoying the unfolding tragedy.

Later, at our table, after most of the heat died down, a server quietly slipped me a note as we worked on after-dinner beers. I read the note and blushed again, prompting my date to ask what it said. I didn’t want to tell her, but she managed to steal it from me and read it aloud: “Please watch your language. There are children here.”

I hadn’t remembered swearing loudly on the deck, but apparently I had, because looking around I saw several purposeful glares. 

“Fuck that,” Annie hooted, and we laughed like the last people on the Titanic, riding it down without a care.

We managed to pay the bill and motor out from the dock without any more incidents, but when I dropped her off in Hope for the end of our date, I leaned in for a kiss and winced as she turned away, pushing me back gently.

“Friends,” she said, graciously. “We’re just friends, right? I told you that before, right? I hope you don’t think I was leading you on or anything… I’m like 10 years older than you.”

I nodded, crushed, and accepted the consolation hug from her.

During the course of the date I had smashed the boat into the dock, unnecessarily upset a poor dog and our server asked me to stop swearing at the dinner table, only to have my attempted kiss rebuffed at the end. 

Driving away, I winced again, realizing I still had three golf lessons to complete with her. I looked down at my lap in shame, noticing one more thing: My zipper was down. 

Worst. Date. Ever.