milking a dead rat

to be involved in an extremely frustrating and tedious activity with unclear or disappointing results. (origin of the phrase is attributed to an archaic Russian jargon).

1) - Why did John drop out of the grad school after 8 years?
- His advisor was nuts. John was milking a dead rat all this time.

2) Dude, trying to sleep with her before marriage is like milking a dead rat.

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