My Online Date Turned Into A Weird Threesome Proposal

Things got weird.

We’ve all made bad choices when it comes to dating.

Odds are good that you have one dating story your friends love to hear you re-tell over dinner on a Saturday night, one that was terrible at the time but makes for a good laugh with a few years between you and your horrors.

Mine involves Hannah Montana, a tractor, and an awkward invitation to a threesome.

There was once a time where Craigslist wasn’t as dangerous of a place to cruise for dates. You weren’t going to find many quality connections, but I dipped my toe in that pool a time or two. I was surprised when a genuinely great woman responded to one of my ads – she lived a few hours away, was a mother of two, and said she was into several of the same nerdy things that I was. We chatted over email about video games, movies and politics, then gradually moved to phone conversations. After another week of those, we agreed on a date to meet up in person. We picked a coffee shop that was central to town and an equal trip for both of us.

I’d spent all morning planning my outfit, so I was crushed when the harried mother called me to confess that her babysitter for the evening had cancelled and she had no way to come out and meet me, “But if you’re willing to drive out here, I’ll have a dinner waiting for you.”

I really wanted to meet her, and I was impressed by her dedication to her children. Rather than stick them with someone last minute she decided to try and salvage the situation in a way that allowed her to still look after her kids. I quickly agreed, and it wouldn’t be until I actually started driving up there that any sense of trepidation would start to sink in.

The part of town she lived in was pretty typical for a rural outskirts town, but my 22 year-old self had lived a lot closer to the city her entire life and was in no way prepared for the reality of how remote the area was. As my car rumbled down an unpaved gravel road, I started to note things like how dark it was, how far apart the lights were, and how we were surrounded more by trees than actual homes.

Her trailer was tall and well settled; there was a small set of wooden stairs that climbed from the driveway to her front door. I sat there in my car and pictured every horror story I’d read on the internet, every time I’d shouted at my friends for making such unbelievably stupid decisions in their stories, and shrugged. What were the odds? I went inside.

The two kids were still up, helping themselves to a microwave dinner before being tucked off to bed. Once they’d been introduced and had gone off to sleep, she turned to me with a smile and asked me what movie I’d like to watch. We hadn’t had a lot of time for small talk since I’d gotten there, but we had several conversations about our interests. Knowing we shared similar tastes, and knowing that mothers don’t often get to choose their evening movies, I told her to pick out anything she liked.

She picked the Hannah Montana movie.

Not to knock on Hannah Montana fans, but learning about the woes of being a teenager leading a double life in the country isn’t exactly the most romantic thing in the world to watch on a first date. Not to mention it was pretty far from the science fiction and action films we’d shared a similar interest in before. Every time I tried to ask her a question or make a comment she shushed me, like I was talking through the key moment in a major sports match.

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The movie wasn’t even over before I knew this wasn’t going to work out. We had no chemistry on top of everything else, so I started planning my escape after the film. When it wound down I said I had a long way to drive and I ought to get going. Purse in hand, I poised myself in front of her door, which was open with a closed screen door to let in a bit of air. She chatted with me for a little while longer, though I noticed she kept glancing over my shoulder and out the front door. I didn’t want to be rude so I didn’t turn away – not until I heard the rumbling, at any rate.

She grinned and I turned around, squinting into the darkness. A single light bounced against the gravel road, and as it got closer I saw what it was. A tractor. More precisely it was a man riding a tractor, which he then parked squarely in her front yard.

As he bounded up those same wooden steps I had, my date opened the door, ran into his arms, and introduced the man as her husband.

So I feel like I should take this moment to offer a bit of advice to threesome seekers out there.

One: you should probably let your would-be date know in advance that this is what you’re looking for. Lying by omission to them for nearly a month by failing to mention you have a husband in the first place isn’t going to win you any brownie points, shocking though this may be. Secondly; you definitely shouldn’t reveal your interest in this activity by having a creepy guy you’ve never met before stand between said date and their exit, leering at you while armed with a tool belt and a sense of entitlement.

When my panties failed to drop immediately, they seemed to sense something was wrong.

“I thought you should meet,” my date elaborated.

“You know, to make things go more smoothly tonight.”

It wasn’t until those words that I let the reality of the situation sink in fully. This was actually happening.

I had to escape, fast. I got the guy talking, and he did his best to woo me with stories that depicted his manly daring, including one in which he told me he used to copy the DVDs he got in from Netflix until he sent a copy back by accident instead of the actual DVD and that’s why he was banned from the service now.

Sometime during our conversation, he relaxed and moved over towards the couch, and that’s when I made a bee-line for the door. I reiterated that I was tired and had a long drive, and before they could even get up off the couch, I waved goodbye and made my way to the car as fast as I could.

The drive back home was as surreal as the event itself had been, and I wasn’t certain what to make of it all at the time. I only knew one thing for sure: Craigslist was crossed off my dating pool list, for good.

Comment: Do you have a dating horror story?