The context of the following conversation is Jordan told Bob that they would take them for a drink if they won.  Jordan held up their end of a deal.:
Jordan says Well, I guess I lost that bet with Bob. Teaches me not to get in these situations..
The friend responds I still can't believe that he won, it was such a close game and his team won by a last minute winner..
Jordan responds The bet was so much fun, I'm mad I lost but we laughed it off over a drink I owed him in the end..
The friend responds Good stuff..