What's the most awkward situation you got yourself into that actually ended in your favor with great benefits?

I was once roped into a 'quick poker game' by a couple of mates.

I only knew two people, but they needed me to make the numbers up. So i caved and said I would. This was a tuesday night and I had to be up for 6.

Once I get there, it becomes immediately clear it's not just a quick game, but actually a bunch of blokes 10 years older than me getting hammered, playing cards and doing large amounts of various substances.

When we eventually sit down to play, the host shouts 'Right lads, £30 buy in, lets go!'. Now I wasn't too flush with cash, and £30 would have been half of my going out money for that week, but feeling the pressure, again I caved, putting my money down and getting my chips. I was regretting it already. These were MEN, and I was 19. I planned to play this game, make my boyish excuses and leave.

I figure now i'm in for the long haul and hadn't driven, ill sink some beers and have a smoke. We play, the players thin out until its down to just me and the host. I'm way out in front, so agree to let him keep his£30 for another game and I'll take the rest.

£240 well made. We went again for £20 each, and I won, one guy had to bet his Fossil watch, which I also won. I felt bad and tried to give it back and he got pretty offended saying 'real men pay their way lad, it's yours'.

So I came out with £400 and a cool new watch. I was really hungover the next day, vomiting and such from the drinking until 2AM.

/r/AskReddit Thread