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Buy a lottery ticket every month for a year
 
       
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On 27 lists and 4 people have done it.
 
Bought an escalating number of tickets (1 in Jan, 2 in Feb... 12 in Dec). Total spend = $156. Total winnings for all those tickets = $28. Net loss was a whopping $128, which would have gotten us a few nice date nights. Turns out that, as expected, lottery tickets are not the wisest investment.