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.
(..) - Yes, I am, - And are you a member, Judge? - My husband was once, One day he took our adopted son with him to the club, It was a painful experience, We've decided it's in the best interest of the city to drop the murder charge and not pursue another lengthy trial, Isn't there evidence (..)1994 The Glass Shield