に結婚を申し込んだ

proposed marriage to

→ に
phrase Rare #42,261
proposed marriage to The に marks the person being proposed to. 結婚を申し込んだ is the past form of 結婚を申し込む, meaning “to propose marriage”; it is somewhat formal and can also be expressed as プロポーズした.
JA: 彼は長年付き合っていた彼女に結婚を申し込んだ。
EN: He proposed marriage to his longtime girlfriend.