There’s no nice way of dressing this one up, so let’s just dive straight in: to suffer a moll’s three misfortunes is to ‘break a chamberpot’, ‘beshit the bed’, and ‘cut your arse’.
Or at least it is according to Eric Partridge’s superb Dictionary of Slang and Unconventional English (1937). With extra emphasis on the ‘unconventional’ there, admittedly.
So. Two questions: why, and—like, seriously, why?
Well, firstly, as we explained on Twitter, there’s a good reason why beds and chamberpots are mentioned here. Moll is an old nickname for a prostitute, in which sense the name has been kicking around in English since the early 1600s. It was also once a nickname for a female pickpocket, while the gallows were known as a Moll Blood, and a mollshop was a brothel. There is some good news for any Mollies who might be reading this, however, because a Moll can also be a sweetheart or girlfriend, or a dear female friend or close companion.
Why such extremes of meaning? Moll is a pet form of the name Mary which (as we’ve also mentioned on Haggard Hawks before) has historically proved one of the most consistently common girls’ names out there.
And it’s nothing more than that commonness that led to Moll being attached as a slangy nickname to just about anything and everything over the centuries—including, alas, some pretty unpleasant characters, and all they bring with them.