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に微笑みかけた

smiled at

→ に
phrase Rare #36,415
smiled at The に marks the person being smiled at. 微笑みかけた is the past form of 微笑みかける, meaning to smile at someone or direct a smile toward them.
JA: 先生は私に微笑みかけた。
EN: The teacher smiled at me.

彼女は赤ちゃんに微笑みかけた。

She smiled at the baby.

彼らはお互いに微笑みかけた。

They smiled at each other.

彼は女の子に微笑みかけた。

He smiled at the girl.

彼は振り返って私に微笑みかけた。

He turned around and smiled at me.