"I keep track, you know." Because, as her boss, her hand to, but also because he was curious. Very curious. It usually got him into trouble in the end, but Jefferson wasn't a very cautious person.
"Important work with school? Helping your boyfriend with something?" Was he prying? Maybe just a little. His tone was light, though. Playful as it usually was. Jefferson didn't hold a stern or serious tone unless it was absolutely necessary.
"Girl troubles?" He had a daughter and had had a wife. He knew of these things.