I like how he put a soft look on his face when he is with his friends around. 彼が友達と一緒のときにだす柔らかい表情が好きです。 does this sound natural?

The Language Level symbol shows a user's proficiency in the languages they're interested in. Setting your Language Level helps other users provide you with answers that aren't too complex or too simple.

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  Has difficulty understanding even short answers in this language.

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