Spin City (1996)

S6E7 Sleeping with the Enemy

As the mayor gears up for a debate against his rival, Charlie finds himself dating Jennifer, the rival's campaign manager, for three weeks. The mayor urges Charlie to end the relationship, but he refuses. One night, the mayor pays Charlie a late-night visit to reveal potentially damaging information regarding the campaign, but Jennifer might have caught wind of their conversation. Meanwhile, Paul and Robin's connection deepens, with Paul viewing it as a budding relationship while Robin perceives it as a casual fling.