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He painted the door red so that it would match the walls.

If he had painted the door red it would have matched the walls.
Which of the following sentences is grammatically correct, after combining the above two sentences ?
1. If he had painted the door red so that it would have matched the walls then I would be happier.
2. If he had painted the door red so that it would match the walls then I would be happier.
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Debpriya DeHe painted the door red so that it would match the walls.If he had painted the door red it would have matched the walls.Which of the following sentences is grammatically correct, after combining the above two sentences ?1. If he had painted the door red so that it would have matched the walls then I would be happier.2. If he had painted the door red so that it would match the walls then I would be happier.
Red walls! Unusual.

In the second sentence, the condition implies that he did not paint the door red, as was desired, but the "so that" clause implies that choosing a color that matches the walls is still possible. These two factors contradict each other.

I find that the first sentence makes more sense, though it is more awkward than necessary. Other versions work even better:

I'd be happier if he had painted the door red so that it (had) matched the walls.

CJ
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CJ, could you please elaborate on why "If he had painted the door red so that it would match the walls then I would be happier." is not correct ? I didn't quite catch it.
Debpriya DeCJ, could you please elaborate on why "If he had painted the door red so that it would match the walls then I would be happier." is not correct ? I didn't quite catch it.
"so that it would match" seems forward-looking to my ear. (He painted the door so that it would match ~ He painted the door so that it was going to match ~ His intention, when he painted it, was to make it match.)

"if he had painted" seems backward-looking to my ear. It's counterfactual. (If he had painted the door red -- but he didn't -- ...)

So the combination sounds to me like He didn't paint the door red so that it was going to match the walls or He didn't paint the door red with the intention, when he didn't paint it, of making it match the walls. In short, the explanation of the motivation for doing something ("so that ...") doesn't seem to go with the fact that nothing actually happened.

The combination of tenses is probably not technically incorrect, but, as I showed, there are more natural ways to say it. Even so, note that if you said that sentence, your listener would understand you just fine by using his common sense.

CJ
You're right, CJ. I could use more unambiguous sentences.
But I have another question regarding the would/would have structure.

"You stole my pen."
1. Why would I steal your pen ?
2. Why would I have stolen your pen ?
Which of the two sentences is grammatical and more natural ?
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Debpriya DeYou're right, CJ. I could use more unambiguous sentences.But I have another question regarding the would/would have structure."You stole my pen."1. Why would I steal your pen ?2. Why would I have stolen your pen ?Which of the two sentences is grammatical and more natural ?
They are both fine. These choices are similar to those in your previous question. The second one is probably the more logical, since the original statement is in the past, but in that situation people do often say the first one instead to indicate a sort of timeless claim that they would never steal anything.

CJ