Roger's feelings about Tamsin can be summarized as "Oh." He doesn't care what she does with her life, but neither does he understand it.
Roger flirts with Lucy (in a good-natured, not necessarily serious way) everywhere but on the pitch. There, he screams at her to get her act together like every other one of his players. And then quickly resumes attempting to write a play that will cause her shirt to lift up far enough that her bra's visible. Because a man's got to have priorities, goddammit.