Tulsa you in effect had the right idea. You ask which road would your brother send me to happiness if I asked him.
If road "A" is happiness, the brother who lies all of the time would point you to road "B", lieing about which road his brother would send you down.
If you asked the brother who tells the truth, he too would tell you his brother would send you down road "B".
Thus you would go down road "A" and never have another losing bet, but would that be fun knowing every bet you placed was going to win?