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To be 'in a pickle' means to be in trouble or a difficult situation. What I'm wondering is, where did the root of this phrase come from and what's its history? Is there a special story that caused this phrase to catch on? Was it someone almost being pickled?

Funny thing is, that I was actually eating a pickle when I thought of this.

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    If you find a "special story" that seems to account for a particular strange or entertaining phrase, it is almost always a complete fabrication. There are no doubt a few well-documented cases where a phrase arises from a particular event (and more where it is a "catch-phrase" from a particular entertainment, such as a radio programme). But most such stories circulating on the web have no basis in truth. People invent them for whatever reason (perhaps in good faith) and they get circulated because we love a story, and the truth (often "We just don't know") is not nearly so attractive.
    – Colin Fine
    Apr 29, 2011 at 12:35
  • Probably some "silly" Dutchman... : )
    – user65320
    Feb 10, 2014 at 18:23
  • Its one of those expressions that we really don't know how it came about. I think it came to mean being in a predicament while someone happened to be eating a pickle. The phrase makes more sense than being in an orange! It just doesn't have that same ring to it! LOL
    – Jonathan A Train
    Dec 27, 2016 at 21:43
  • Just a technology note. The manufacture of vinegar for pickling and alcohol for preservation/sanitizing involved the exact same processes, both in the home and at scale for military logistics. In the case of vinegar, the ethanol is converted to acetic acid by bacteria. Indeed, whether you ended up with wine or vinegar was largely happenstance back then. If the vinegar reaction didn't run properly, it was likely because of too much methanol - ill pickle indeed.
    – Phil Sweet
    Dec 28, 2016 at 1:38

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Etymonline offers this:

pickle mid-15c., probably from Middle Dutch pekel "pickle, brine," from a Low German root of uncertain origin or meaning (cf. [...] German pökel). [...] Figurative sense of "sorry plight" first recorded 1560s.

The Phrase Finder supplies some background:

The figurative version of the phrase, meaning simply 'in a fix' [...] arrives during the [16th] century. Thomas Tusser's Five Hundreth Pointes of Good Husbandrie, 1573, contains this useful advice:

Reape barlie with sickle, that lies in ill pickle.

[...]

There are a few references to ill pickles and this pickle etc. in print in the late 16th century, and Shakespeare was one of the first to use in a pickle, in The Tempest, 1610 [Act V, Scene 1, Line 2354]:

ALONSO:
And Trinculo is reeling ripe: where should they
Find this grand liquor that hath gilded 'em?
How camest thou in this pickle?

TRINCULO:
I have been in such a pickle since I
saw you last that, I fear me, will never out of
my bones: I shall not fear fly-blowing.

Follow the links for additional insight.

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According to Wiktionary it was first used by William Shakespeare and imported from Dutch:

http://en.wiktionary.org/wiki/in_a_pickle#Etymology

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    Leave it to Shakespeare to make something ridiculously odd like this up.
    – James Mertz
    Apr 28, 2011 at 22:13
  • Get off Shakespeare's case - he wasn't the first.
    – slam
    Feb 10, 2014 at 22:54
  • A character called Golding asks a falling-down-drunk friend in 'Eastward Hoe' (1605) 'Fie! fellow Quicksilver, what a pickle are you in?' To which Quicksilver indignantly replies 'Pickle! Pickle in thy throat! Zounds, pickle!' So even then they objected to it as kind of stupid. Or drunks did, anyway.
    – slam
    Feb 10, 2014 at 23:03
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shakespeare first said it. Meaning: a difficult or uncomfortable situation.

In “The Tempest,” King Alonso asks his jester, Trinculo, “How camest thou in this pickle?” (In modern language, “how did you get so drunk?”)

The drunk Trinculo responds, “I have been in such a pickle since I saw you last …” (Act 5, Scene 1).

Trinculo’s drinking does cause trouble for him, the way we use the phrase today. Shakespeare’s original intent makes sense though. Many pickling processes use alcohol.

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