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.
(..) It's just a barbecue. No big deal. You wanna come along? Well, actually, my crew has invited me out for a drink. Ooh, progress. Well, however slow, however painful, I think they're coming around. Give me a few minutes. I'll give you a lift. Okay. Cool. I got the next game! (..)1997 G.I. Jane