The most intuitive way (well, only intuitive way) I can think of to explain why the logic "I have a 50/50 chance of winning/losing" and "if I win then I gain more than if I lose" is faulty is because, particularly if this were to happen in the real world, the wives would not spend some amount of money on a necktie that could like anywhere within the range of positive real numbers. There would have to be some probability distribution of how much money they could spend on a tie. As soon as you create a probability distribution from which the two ties are drawn, it becomes clear that the more valuable your tie is, the more likely you are to lose the bet.