Originally Posted by LuciferMutt
I'd bet dollars to donuts (wtf does that even mean)
Dollars to donuts is a faux bet in which one person agrees to put up the same amount of dollars to another person's donuts in a bet (where a donut is considered to be worth much less than a dollar). Betting someone dollars to donuts is a rhetorical device that indicates that the person is confident in the outcome of an event, but it does not usually involve an actual bet with actual payoffs (either in dollars or in donuts).
Betting dollars to donuts may not be such a good bet today. When this phrase was coined, you could buy many donuts for a dollar. Today, when a donut often costs more than a dollar, the bettor who bets dollars to donuts is actually making a bad bet.
Other versions of this phrase have been used in the past: "The almost forgotten terms 'dollars-to-buttons' and 'dollars-to-dumplings' appeared in the 1880s, meaning 'almost certain' and usually used in 'I'll bet you dollars-to-buttons/dumplings.' They were replaced by 1890 with the more popular 'dollars-to-doughnuts' (a 1904 variation, 'dollars-to-cobwebs,' never became very common, perhaps because it didn't alliterate)."