They made it 'painfully' obvious/clear that we were not welcome. [=they made it very clear in a way that was rude or upsetting that we were not welcome]
His ankle is swollen and 'painful to the touch'. [=his ankle hurts if he touches it]
After the injury she was 'painfully' aware that her career in tennis would be over.
(..) You. Listen, I'm sorry. But there was a disturbance. I don't know you. And I can't keep thinking about you. I's too painful. I've been reading poetry lately. Whatever that means. Day by day he gazed upon her... Day by day he sighed with passion Day by day... (..)2004 Spider-Man 2