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Context: A divorced father has had his son over for a few hours and they ended up having a heated argument that ruined the evening. His ex-wife talks with him two days later. She is angry and says this:

What happened? Why couldn't you just have had a fun time with him?

Is this sentence phrased grammatically correct and natural for the context (in particular "have had")?

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It's grammatically correct. In conversation, I think it would be more natural to say "Why couldn't you just have fun with him?", or "Why didn't you just have fun with him?".

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