Why did he ask his coworker....

Ok, at one point in the movie, he asks his lady coworker if the two of them were "cool." He said, "we're cool right?" or "we're good right?" (or something to that effect). She said yeah, and he kept pressing, and she said, "get over yourself"

Ok did I miss something? why did he ask her that? Did the two of them have a fling or affair at some point? or did he think she had a crush on him? I don't understand why he was even asking her that. Did she do something? I think i may have looked away from the movie for a brief moment so i'm wondering if I missed something that would explain that part.

Thanks for your help!