Have You Ever Had a Conversation About Betting With a Stranger That Turned Unexpectedly Honest?

[oli_sussex]

Happened to me on a train from Brighton to London last year.

Man in his sixties. Suit. Reading the Racing Post. We made eye contact when I sat down. He folded the paper. I thought he'd go back to it.

He asked if I followed racing. I said not really. Said I was more of a football markets person. He nodded like that was a complete sentence.

Then he said: "How long have you been trying to quit."

Not a question about whether. Just how long.

I said I hadn't been trying to quit.

He looked at me for a moment and went back to his paper.

I spent the rest of the journey wondering what he'd seen. What the answer would have been if I'd been honest.

The conversation was four sentences. It's stayed with me longer than most.

 

[TaffyTipster]

Long train journey. Cardiff to Edinburgh. Years ago.

Bloke about my age. We got talking because of a rugby match showing on the carriage screen.

Few hours in, somewhere around the Midlands, he mentioned he'd had a problem with betting a while back. Said it almost accidentally. Like it came out before he'd decided to say it.

I said my betting was pretty heavy too.

He said: "Does your wife know how much?"

I said not the exact number.

He said his hadn't either. Said by the time she knew the number the marriage was already in a different place.

Then the announcement came for his stop. He got his bag from the overhead. Said it was nice talking.

Never got his name.

 

[SharpEddie47]

Business flight. Dallas to New York. 2016.

Man next to me noticed I had a statistical model open on my laptop. Asked if I was a quant. I explained it was sports betting analysis.

He was quiet for a moment. Then told me he'd been a professional sports bettor in the nineties. Said the books hadn't been as sophisticated then. Said he'd made real money for about seven years.

I asked why he stopped.

He said: "I realized I was better at it than almost anyone I'd met and I still wasn't happy. That seemed like important information."

He slept for the rest of the flight.

I didn't.

That sentence has been sitting in the back of my head since 2016.

 

[FadeThePublic]

Hospital waiting room. Not me. Waiting for a friend who'd had a minor procedure.

Man next to me. Fifty-something. Watching something on his phone with the sound off. I could see it was a football match.

We started talking the way you do in waiting rooms. Found out he followed the same team I'd been watching.

Somewhere in it he said his son had asked him to stop betting. Said his son had found out how much he was spending and had sat him down like a parent sits down a child.

He said it with this particular tone. Shame but also something else. Almost pride that his son cared enough.

He said he'd told his son he'd cut back. Said he hadn't cut back.

He'd been in that waiting room for three hours and I was the first person he'd told that to.

He didn't know me. Didn't need to manage what I thought of him.

I think that was the point.

 

[ParlayPrincess_88]

Uber. About a year ago.

Long ride. Driver was playing some game on his phone at red lights. I asked about it. Turned out it was a betting app.

He asked if I bet. I said yes. He asked how I was doing.

I said honestly I was probably down a bit overall.

He laughed. Not mean. Just like I'd said something true.

Then he told me his whole thing. How much he'd won on a parlay three years ago. How that win had basically determined every bet he'd placed since. How he was still chasing that specific feeling.

He said: "I keep thinking if I hit it once I can hit it again. But I think I just got lucky once and I've spent three years paying for it."

We were at my destination. He finished the sentence as I was getting out.

I've thought about him a lot.

 

[CoachTony_Bets]

Coaches convention. Few years back.

Guy I'd never met. Different conference. We ended up at the same table at the evening dinner.

Found out he coached high school like me. We talked football for a while.

Then he mentioned something about being glad the conference ran Thursday to Sunday. Said he had to be careful around Monday Night Football.

I knew what that meant.

I said I had some of the same issues with games during the week.

And then we just talked honestly for about an hour. About the hiding it. About doing the analysis under the table during family dinners. About the specific way it changes how you watch games you love.

Neither of us performed anything. Neither of us tried to make it sound better than it was.

At the end of dinner he said: "Glad it's not just me."

That was all.

Haven't seen him since. Don't know his last name.

But for that hour I wasn't the only coach at a school event secretly managing a betting habit.

That mattered more than I expected.