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David_J_Balan comments on Rooting Hard for Overpriced M&Ms - Less Wrong
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On the contrary - if the bill had been $5 instead of $1, then your bank account would have had $4 less in it, and you couldn't have generated the gains from trade.
Paradox cleverly resolved!
(Actually, I suspect the real answer is that you have a "warm" preference for M&Ms over $1 and a "cold" preference for $5 over $1. System 1 vs. System 2.)
I think the answer in the parenthetical is probably closer to the mark. But it's still the case that even in the "warm" moment I wouldn't have paid $5+ for a bag of M&Ms, so it doesn't totally work.
I think there are two questions being resolved:
Your happiness was strictly a result of answering YES to question 1, and it was a System 1 judgment that happened before you had time to think about question 2. The subsequent realization that YES on #1 implies having $4 less than NO (via question 2) is a System 2 judgment, so it didn't occur until (much) after the happiness had occurred, and because it is System 2 rather than System 1, the feeling that it would have been better if it were a $5 doesn't feel anywhere near as strong as the feeling that you can get M&Ms.