“My Boss’s Daughter” (2003) My Boss’s Daughter, a 2003 romantic comedy directed by David Zucker, stars Ashton Kutcher as Tom, an eager young man who gets the chance to house-sit for his intimidating boss—only to be entangled in a series of chaotic mishaps involving unexpected guests, drug dealers, and the boss’s alluring daughter, Lisa, played by Tara Reid.
At the center of the film’s tension and attraction is Lisa, who embodies a classic early-2000s ideal of beauty: blonde, tanned, stylish, and effortlessly seductive. Tara Reid’s portrayal leans into this image—Lisa is the kind of girl that the male protagonist (and the audience) is meant to fall for immediately. Her beauty is the main draw, and much of the film’s premise rests on Tom’s awkward, eager efforts to impress her while keeping things from falling apart around him.
Lisa’s character is framed almost entirely through the male gaze. She is the object of desire, not necessarily for what she says or does, but for how she looks and how she functions as the “prize” at the end of Tom’s comedic ordeal. Her gender and appearance are used narratively to generate stakes—Tom doesn’t just want to survive the night without upsetting his boss; he wants to win over the beautiful daughter.
But while Lisa’s role is largely ornamental and idealized, there are moments where her character subtly pushes against expectation. She’s not simply a damsel or eye candy—she’s clever, sarcastic, and aware of how men view her. In a film that often trades in exaggerated stereotypes and slapstick, Lisa still hints at a more knowing self-awareness than the premise fully allows.
My Boss’s Daughter reflects a moment in early-2000s pop culture where female beauty was frequently exaggerated and idealized for male-led storylines, but it also subtly acknowledges how that ideal can be both powerful and reductive. Lisa’s character is attractive, yes—but she’s also framed in a way that reveals how much romantic comedies rely on appearance to justify connection, desire, and even plot progression.
