Pictures:

Why was Bobby's mother concerned with he came home from school with this sheet of paper?

He came home with a black 'i'.

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What is it called when two people argue about who won a contest?

They're contesting the contest.

3321

What was Jim's reaction when the other poker player wanted to deal the cards?

Well, it's not ideal.

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What chess term refers to a marriage that needs to be re-invigorated?

Stalemate.

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What is the difference between an orange and a bad law?

An orange is peeled, and a bad law is repealed.

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Why did Betty enjoy the Uber ride?

It gave her a lift.

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After someone stole Bobby's clothes while he was swimming, did he get home without people seeing him?

Yes, but just barely.

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What rap singer also told puns?

Rapunzel

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Why did Kay feel that she could do whatever she wanted?

Because whenever she did something strange, people would say Oh Kay!

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How did the Teddy Bear feel after dinner?

It felt stuffed.

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What do athletes and musicians have in common?

They want to make records.

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How would you describe a woman in trouble, if all you can identify is her dress?

A damsel in this dress.

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