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Is it correct to say, “He was the happiest when”?

Someone recently came to my website from Google after searching for the following question:

Is it correct to say that he was the happiest when…?

And I thought it seemed as good as any other question for me to answer.

Happiest is the superlative form of happy. That means it’s the highest level of happy, and like happyhappiest is an adjective. We use it as a way to describe other things, for example:

In every example, happiest describes something: the happiest period, the happiest person, the happiest story.

The problem with the original question is that it’s missing something—the happiest what? Personally, I’d probably rewrite it to be something like, “He was at his happiest point when . . .

Do you have grammar questions? Let me know in the comments.

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