We were playing around the other night with homophones which have multiple meanings. I'm wondering who can come up with the most in one sentence? My best so far is...

Would you check a cheque in payment of his check from a Czek wearing a jacket with a check in the pattern?

That's FIVE

As a related game, it might be fun to add a rule that the homophones must all have different spellings.

Consider the ram who found that the females of his flock were all shying away from him, indeed leaving the area en masse for greener pastures. With pithy precision, he called out, "Wait! I can use youse ewes."

Speaking of the Deadly Sins, which we were not, let's list lust last lest lust be lost.

I'm sure this fits no rules, however:

BobHale arrived in a hellacious hail storm, and we all greeted him with hale and hearty welcome; and then we haled him into court.

A Wind In The Willows sequel.

Ratty set his chess set on the table at Badger's set and proceded to set it up but Badger was set against playing.
"I'd like some Jelly" said Mole.
"It isn't set." snapped Badger who was setting the clock to British Summer Time to set an example to the others who always forget. Meanwhile Mr Toad was setting off to visit them and watching the sun set as he strolled towards the Wild Wood.
"Why it looks just like a stage set" he mused as he walked. The wind was set from the east and it was a pleasant evening and he was looking forward to being among his set again. Had they come to him off course they could have played a set or two of tennis but Badger's entertainments were more modest.
"Dear old Badger." thought Toad, "So set in his ways. We can't even watch TV, he doesn't have a set. Pity, Britney is on tonight."

He arrived at Badger's and set his hand against the door.
"Come in" cried Badger "And set yourself down", we'll set up the radio and listen to Britney for you, I know you were dead set on hearing her set."

I am rather sheepishly admitting that Hic's version makes for a challenge I hadn't thought of. However, the flip side is using a word spelled the same with multiple different meanings in the same sentence. ie:

The ram hit the door, knocking the plug out of the wall, and my computer emptied its ram, dumping the picture of my prize ram that I had intended to ram down the throat of the other breeders.

My company will, for a very small fee, deliver a gift of perfume. Our slogan?

Scents sent for mere cents.

wow! I surrender. That is wonderful.

I see that I could cross the seven seas and still not sieze anything better.

The promotion of coffee and teas through the use of photos of young women in jeans and wet T's could backfire since, as is well known, nobody likes a tease.

Jerry Thomas lays about his home waiting for visitors from the mainland, presents them with leis when they arrive, and then invites them to laze a while on the beach.

A book on the early days of psychotherapy: "Back When Jung was Young." (Only two uses, yes, but the title appeals to me.)

(For R.E.) In baseball, especially as played in England, the thrill of the game comes not from its swings and misses; it's from the 'its.

The sheep, all whites and greys, go to the fields to graze along with the aardvarks.

(No, wait. That last one needs work.)

quote:

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Jerry Thomas lays about his home waiting for visitors from the mainland, presents them with leis when they arrive, and then invites them to laze a while on the beach.

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lies !!!

Happy daze !!

So far, the responses have been fascinating. One of the difficulties of teaching English is multiple and very different meanings for the same word. cf my piece on check and BH's Wind in the Willows on set. Although I am a psycholinguist, I do not know a lot about languages other than English, so I am not aware if this a peculiarity of English.

Imagine the difficulty of learning the meaning of this sentence, if you are not a native English speaker.

"Would you play your cello just for play, during the first intermission of the play?