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.