The context of the following conversation is Once Lee became upset and started to cry, Riley stopped teasing Lee.:
Riley says Oh man, I felt so bad..
The friend responds What happened?.
Riley responds I was teasing Lee about his break up and he started to cry..
The friend responds Wow, you must've really upset him..
Riley responds I did. I didn't really think he cared about the girl. I stopped teasing him as soon as I realized he was in pain..
The friend responds I'm sure he'll understand. You two are always teasing each other..