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Example sentence: 雖然當我們在一起的時候有時候我不常常說話、而且我可能正顏厲色、我要讓妳知道我很開心。

Intended meaning: Although when we are together sometimes I don't talk very much, and also my face may be solemn, I want to let you know I am happy.

Is there a specific order? My second guess would be:

當我們在一起的時候雖然有時候我不常常說話、而且我可能正顏厲色、我要讓妳知道我很開心。

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Is there a specific order for 雖然 and 當...的時候?

No, I do not think there is a specific order for 雖然 and 當...的時候

A way to see the reason is that , you can insert commas in the sentence and see that 當...的時候 is a adverb clause, and 雖然... is a conjunction word.

(1) 雖然, 當我們在一起的時候, 有時候我不常常說話, 而且我可能正顏厲色, 我要讓妳知道我很開心。

(2) 當我們在一起的時候, 雖然(,)有時候我不常常說話, 而且我可能正顏厲色, 我要讓妳知道我很開心。

(3) 當我們在一起的時候, 有時候我不常常說話, 而且我可能正顏厲色。 雖然這樣, 我要讓妳知道我很開心。

雖然這樣 is a way to connect a subordinate clause in Chinese.

There is a order for 雖然...但是...

雖然媽媽總是批評你,但是她還是很愛你的。

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From your English I would get this:

Although, when we are together, sometimes, I don't talk very much and also,my face may be solemn, I want to let you know I am happy.

尽管有时候,我们在一起时,我不说话而且看起来很严肃,但是你必须知道,我心里很高兴跟你在一起

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