Advice for gambling with someone you don't know...

No offense intended, but race to 7 for $20???

I played race to 5 for $20 over 20 years ago, and that was just friendly competition among friends.

No way I would consider race to 7 for $20, "gambling"

Oh, I guess you could call penny ante poker "gambling" too, so whatever floats your boat.
Do you go to the pool room every night and give up the nuts for $20.00 a set and lose a $100.00? Because as you say "It isn't real gambling".
 
The guy could have decided it was worth the 25$ investment (after table time) to book a loser to you, in hopes of more action from you/friends later. I mean your posting on the internet about it, so if thats what he was doing, mission accomplished. Don't road players work a room/town for days to weeks before setting up the big game and getting on to the next town?
 
I started gambling to bring out my best game and improve but I was too focused on the money aspect.

If this is the case then the stakes were probably just right. Ignore all of the bashers putting down the stakes you were playing at. They don't have to pay your rent.

When your just learning to gamble the stakes should be enough to keep you interested but not enough to let it stress you out. Sounds like you were right on the edge. When you book a game, consider the money gone and fight like hell to get it back.
 
Believe it or not there people who gamble at pool and are not great players just like there are pool players who gamble at dice or cards and lose their money.

If you are worried about him being a hustler, keep it limited to small money and you won't get hurt.
 
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