Which boss does Rebecca Howe have a crush on in her debut season?

Rebecca Howe has a crush on her boss Evan Drake in her debut season of Cheers.

Rebecca debuts in season 6, after Sam Malone’s boat is lost and the bar comes under corporate management. Evan Drake, played by Tom Skerritt, is her senior executive at the Lillian Corporation and becomes the focus of her first major romantic storyline.

Her attraction is largely one-sided. Rebecca tries desperately to impress Drake and make him see her romantically, often turning ordinary business situations into elaborate, embarrassing schemes. The comedy comes from the contrast between her polished professional image and her increasingly anxious behavior around him.

Viewers sometimes confuse Evan Drake with Robin Colcord, another wealthy corporate figure who later becomes central to Rebecca’s relationships. John Allen Hill is also a frequent source of romantic tension, but he is primarily Rebecca’s competitive business rival. Drake is the specific boss tied to Rebecca’s season-6 infatuation, making him the canonical answer to the question.