Q: What is the best time to go to the dentist?

Q: What is the best time to go to the dentist?
A: Tooth-hurty


This is a pun. The words "tooth-hurty" sound both like two-thirty, and "tooth hurt". Two thirty is a time (and a reasonable time to go to the dentist) and since dentists help people whose teeth hurt, "tooth-hurty" is sort of like saying "when your teeth hurt".

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