Lovely; dear; feeling affectionate fondness toward someone or something.
赤ちゃんの寝顔を見ると本当に愛おしい気持ちになる。
Seeing the baby's sleeping face makes me truly feel affectionate.
長年使ってきた古い時計が愛おしい。
The old watch I've used for years feels dear to me.
彼の不器用な優しさが何だか愛おしい。
His awkward kindness somehow makes me feel affectionate toward him.
Pitiable; evoking sympathy — feeling sorry for someone or something.
道端で震えている子猫の姿があまりに愛おしかった。
The sight of the kitten trembling at the roadside was so pitiable.
試合に負けて泣いている彼女の姿を見ると愛おしく思った。
Seeing her cry after losing the match made me feel pity/affection for her.
困難な状況にいる友人の話を聞いて、どうにか助けたいと愛おしく感じた。
Hearing about a friend in a difficult situation made me feel I wanted to help—pity mixed with affection.