I always gamble with my best friend. Having the same bet with them can have both positive and negative aspects. Positive in a way that you'll feel comfortable and supported, especially when losing, just laughing it off. And negative in a way that there will be times that the two of you will have differences in opinion and strategies. It creates pressure on confirming the final decision of the bet. Although, sometimes, listening to them can always get insights that they have a point.