2

I want to say

My manager wants me to introduce my older brother to his younger sister.

My attempt is as follows.

マネージャーは私に弟を妹に紹介してほしがっています。

The problems of my translation above is the ambiguity because who is introduced to who is unclear. 

Should I repeat 私 and マネージャー or 彼 to clarify who 兄 and 妹 belong to? How to say it clearly (without ambiguity)?

4

After some playing around, I've settle on this:

マネージャーは私の兄を彼の妹に紹介してほしがっています。

Notes on the changes made:

  • 私に is dropped and instead 私の is added to 兄. This compresses two phrases (私に and 兄を ) basically into one (私の兄を), with gain in readability and without loss of information. (It'll be still clear who is being ask to introduce "my older brother".)

  • 彼の is added to 妹. 彼の is essential in immediately clarifying whose younger sister is being spoken of. It also helps establish parallelism(?) (私の兄 - 彼の妹), which is cognitively pleasing.

There are other and probably better versions. とりあえずご参考までに!

4

(私は)マネージャー(or his/her actual title) に (or から) うちの兄を 先方{せんぽう}の (or 向{む}こうの) 妹さんに紹介してくれと言われている is what I'd say in that situation.

There are some points.

1) Don't use pronouns like あなた, 彼 or 彼女 when you need to show some respect to him/her (otherwise, you don't have to mind but they are not an intimate expression either). Those words are saved for journalists or critics. Beside うち, こちら/こっち for "I/we", そちら/そっち for "you" and 向こう/あちら/あっち for "they" (when things are going in a closed scheme) are important vocabulary in conversation.

2) Don't use ほしがる when you need to show some respect to him/her. (I personally believe avoiding ほしがる is a useful strategy beyond this case in Japanese composition.)

3) When animate things and inanimate ones are involved, you usually make the former the subject of the sentence and the latter the object, and when two people are involved, make the one who is closer to you the subject.

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