Halfway through our date, I found out he'd been in jail for stalking

In the small Montana town where I used to live, there was about one degree of separation between most people.

That means it’s hard to find someone who doesn’t know someone you know, which makes the dating pool quite shallow.

So when I hit the dating apps in 2015, I knew I’d have to weed through my friends’ exes, plus all the guys who self-described as ‘nonsmokers and social drinkers’, though their barroom habits indicated a different story.

Joss* brought my swiping finger to a standstill. He had classic good looks — think a young Robert Redford — and was so clean-cut I could almost smell the soap through the screen. 

I didn’t recognise him and suspected he was new to town. I located him on Facebook, and we had a handful of friends in common, but most of them I’d consider acquaintances at best. 

At the same time, there was a ruggedness about him, too. He was outdoorsy, and his pictures showed him skiing, sitting around a campfire, or harvesting vegetables from his garden.

We started messaging about our work and hobbies, and I immediately noticed he was clever and articulate. We agreed to meet for a beer and chose a popular happy hour spot near where I worked. 

Earlier in the day, we exchanged phone numbers on the app and agreed on 7pm. We said that we’d meet out front to avoid that awkward moment inherent to most first dates where you’re searching a crowd for each other. 

When I arrived, I discovered the bar was hosting a fundraiser, so the place was packed and loud. I saw many of my friends through the windows and decided it wouldn’t be a good spot to have a getting-to-know-you conversation.

I was still determining which direction Joss would be coming from, but then I saw him inside, working his way through the crowd to come meet me outside.

In some of his photos on the app, he wore a red fleece, which he was wearing the night we met. But now — like Joss himself — the jacket looked a bit worse for wear, as well as ratty and full of burn holes.

In addition, Joss’s short, sun-bleached blond hair had grown to his shoulders and was shapeless, greasy and the colour of dishwater. His handsome face was recognisable, though his cheeks were sunken and were a terrible colour. He was not the vibrant outdoorsman I’d seen in the photos. 

It sounds awful, but I knew I couldn’t be seen with Joss in a busy place, filled with my friends — plus, it was already clear that we weren’t a match — but I wanted to be polite, so after we met, I said hello, and suggested a dive bar a block over.

He told me that his location was monitored by law enforcement. My heart stopped

We each ordered a beer, and he attacked a basket of peanuts like he hadn’t eaten all day. He was thinner than I’d expected — almost gaunt — and although he was recognisable, he had the heartbreaking look of neglect.

He looked and smelled dirty. At one point, I wondered if he was homeless. 

I was wearing a nice dress from work and had even refreshed my mascara. I wanted to laugh, and cry at the same time. 

Truthfully, I really just wanted to get home to my dog.

I thought of the good conversation we’d had while messaging on the app, but Joss seemed disoriented and not like the confident person he’d portrayed himself to be. 

Joss kept scooting closer to me, too, and I kept scooting away. He touched my knee, and I removed it. He didn’t take the hint.

‘I like you,’ he said, leaning in, possibly for a kiss though I didn’t want to take any chances, as I leaned back.

Then, he added: ‘I want to show you something before we go any further.’

I didn’t have a chance to tell him we weren’t going beyond the next 10 minutes before he rolled up his trouser leg and showed me that he was wearing a GPS-tracking anklet.

‘Oh my god,’ I said, nearly falling off my stool. I looked at my beer, which was still more than half-full. I knew I should put money on the bar and walk out, but I’m a sucker for a good story.

I discovered that Joss had impregnated a woman I knew casually — or at least that’s the story he told me. She didn’t want him in the baby’s life, but he didn’t take no for an answer and was arrested and thrown in jail for stalking. 

Now, he was out, but told me that his location was monitored by law enforcement. My heart stopped.

Honestly, it was one of those ‘black out’ moments where I don’t remember if additional words were exchanged, but I definitely knew that it was time to go.

He was on a date with me, while wearing a GPS anklet for stalking another woman – I certainly didn’t feel obligated to explain, or stop to listen to, anything…

I didn’t need any additional information. I couldn’t get the cash out of my wallet and into the bartender’s hand fast enough.

A few months later, I came around a corner at a busy craft fair and was face-to-face with Joss. I hadn’t planned the moment, but I instinctively knew what to do: I looked away and kept moving.  

*Names have been changed

So, How Did It Go?

So, How Did It Go? is a weekly Metro.co.uk series that will make you cringe with second-hand embarrassment or ooze with jealousy as people share their worst and best date stories.

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