What does "pick a lemon" mean? [duplicate]

Related questions:

• What does "lemon on" mean in this context?
• What is the origin of the phrase "when life gives you lemons, make lemonade"?

In the above questions, "lemon" is used to mean a faulty or defective item. A typical use might be to describe a second hand car that, once bought, turns out to have serious faults, as a "lemon".

Why is the delicious fruit associated with faulty goods?

Etymonline says:

• perhaps via criminal slang sense of "a person who is a loser, a simpleton," which is perhaps from the notion of someone a sharper can "suck the juice out of."
• A pool hall hustle was called a lemon game (1908);
• while to hand someone a lemon was British slang (1906) for "to pass off a sub-standard article as a good one."
• Or it simply may be a metaphor for something which "leaves a bad taste in one's mouth."

But none of these rings true for me, and words like "may be" and "perhaps" show a lack of confidence. Can anyone shed more light?

Evan Morris over at The Word Detective, answering a similar query, has some helpful musings.

He argues that despite all the good lemons have done, they've suffered from an image problem since the dawn of their cultivation—due primarily to their stinging acidity and tough skins.

He continues,

The word “lemon” comes to us from the Old French “limon,” which was derived from Arabic roots and served as a generic term for citrus fruit in general (which explains how the same root could also give us “lime”). The use of “lemon” to mean “disappointing result” or “something unwanted” is very old, reflecting the fact that, while useful in cooking, a lemon standing alone is just a lump of sourness with a tough skin to boot. In Shakespeare’s play Love’s Labours Lost (1598), for instance, one character proclaims, “The armipotent Mars, of lances the almighty, Gave Hector a gift …,” to which another puckishly suggests, “A lemon.”

And, clearly drawing from some of the OED citations mentioned by @Barrie, he concludes,

In the mid-19th century, “lemon” was used as a colloquial term for a person of a “tart” disposition, as well as, more significantly for our purposes, slang for a “sucker” or “loser,” a dim person easily taken advantage of. It has been suggested that this latter use stems from the idea that it is easy to “suck or squeeze the juice out of” such a person (“I don’t know why it is, rich men’s sons are always the worst lemons in creation,” P.G. Wodehouse, 1931). By 1909, “lemon” was also firmly established in American slang as a term for “something worthless,” especially a broken or useless item fobbed off on an unsuspecting customer.

It’s likely that the current use of “lemon” to mean “something that doesn’t live up to its billing” or “a disappointing purchase” comes from a combination of “lemon” in the “sucker” sense (i.e., the buyer got “taken”) and the much older sense of “lemon” meaning “something undesirable.”

Also of note, I found occasional use of the phrase (at least as early as 1918), "to give someone a lemon and pass it off as a nugget (of gold)." If this was the original saying, later shortened to "handing someone a lemon," then the implication of trickery is confirmed and the metaphorical use of lemon further explained.

I note the reference to Shakespeare's Love's Labour's Lost, originally flagged by Evan Morris over at The Word Detective and referenced by Callithumpian here. We are given to understand that Hector is given a gift, which is then described disparagingly as a 'lemon'. I think Morris is on to something, but it's more subtle than just a matter of 'sourness' as suggested above. Take the full exchange from Love's Labour's Lost (According to Pauline Kiernan in her 'Filthy Shakespeare', a play notorious for its word play):

*Arm. The armipotent Mars, of lances the mighty, Gave Hector a gift, -

Dum. A gift nutmeg

Biron. A lemon

Long. Stuck with cloves.

Dum. No cloven.*

Nutmegs in Shakespeare's time were astronomically high value items, and given as gifts. Sometimes this is written as a 'gilt' nutmeg. This doesn't change the essential context of Lord Dumaine's remark, he's referring to a high value item. Biron counters by suggesting that the gift is not a nutmeg, but a lemon. Shakespeare at this point is - I'd argue - not using 'lemon' as a metaphor for 'a sour surprise', but rather as a 'cheaper' substitute for the nutmeg. A lemon stuck with cloves (the sharp cloves 'stabbed' into the lemon skin) was a common New Year's gift, something that smelled pleasant and was said to ward off disease. It may also be a reference to the fruit of the nutmeg, which is not unlike a lemon. The rejoinder from Lord Dumaine, 'No, cloven' might be a coded reference to the tendency of the nutmeg fruit to split and reveal a bright red interior, a visual metaphor that I'll leave alone.

I am inclined to the view that Shakespeare's relatively obscure reference has worked it's influence on the English usage of the term 'lemon' as a 'poorer substitute for the real thing', and that this usage has been reinforced over time by the association with the inherent sourness and bad taste of lemons.

The earliest figurative use of the word, in 1863, was, in the OED’s words, as

a person with a tart or snappy disposition. More usually (slang), a simpleton, a loser; a person easily deluded or taken advantage of.

The OED’s earliest citation showing it used as

something which is bad or undesirable or which fails to meet one's expectations

is dated 1909, and in this use it is of US origin. There is also a citation dated three years earlier showing its use in the expression 'to hand (someone) a lemon’ meaning

to pass off a sub-standard article as good; to swindle (a person), to do (someone) down.’

I suppose it’s not too unlikely a progression from being used to describe a person who is in some way unsatisfactory to being used to describe a thing that is is in some way unsatisfactory.