I would have paid him off, not said anything else. Next time you see him and he wants to play, say "we are playing even now, you beat me last we played, its even from now on and we play for at least $10 a game now".
At the risk of sounding female, go to him discuss the situation. Tell him your relationship with him is important to you (ick...bad taste in the mouth). Tell him your feelings (ouch....that hurt). Tell him when he does things like this to you, (oh God...I think I im going to throw up) , it makes you wonder if he really cares (oh crap...my head hurts).
Whew.....ok....I need to go out and kill a small animal now. Then a trip to the titty bar to finish regaining my manhood! Good luck!
This is what really upset me! I always had good friendship feeling to him and many pool regulars, we've known each other for many years, yet he had the audacity to pull something like this;
Thanks to all that replied, i have no intention of playing him again.
There's always 3 sides to every story, so hearing only one side gets you a one sided answer that most likely isn't accurate.
Regardless, the real point, IMO is YOU NEVER GAMBLE WITH FRIENDS, PERIOD.
Why? The outcome in the long run, more times than not, is someone ends up into someone for just enough that someone suggests upping the bet a little. At that point the cancer begins to grow to either an argument at some time , loss of a friend, or at the very least loss of a pool playing partner, and it all starts with a "little friendly 5 dollar bet" In this case, it seems the symptoms of this cancer are beginning to manifest themselves.
What's the point in risking any of that for a small 5 dollar bet?