How to Lose a Guy in 10 Days
Why this pick
Like Working Girl, it turns Manhattan professional ambition into buoyant romantic comedy, with a sharp, determined heroine navigating status games while chemistry complicates the plan.
A FILM WORTH A CLOSER LOOKTHE FEATURE PRESENTATION
IF THIS ONE STAYED WITH YOU
Keep the feeling.
SIMILAR PICKS / A PERSONAL CONNECTION
Why this pick
Like Working Girl, it turns Manhattan professional ambition into buoyant romantic comedy, with a sharp, determined heroine navigating status games while chemistry complicates the plan.
Why this pick
Its polished workplace setting, power reversals, and brisk enemies-to-allies romance echo the pleasurable combination of career stakes and wish-fulfilment charm in Working Girl.
Why this pick
A smart professional woman and her demanding wealthy boss generate the same glossy New York mix of class friction, office banter, and romantic possibility.
Why this pick
This late-1980s comedy shares Working Girl’s warm, stylish confidence in a capable woman reinventing her life without losing its grown-up romantic sparkle.
Why this pick
Ambitious assistants try to manipulate their powerful bosses’ love lives in a breezy, affectionate update of the workplace-romcom energy that makes Working Girl so satisfying.
Finding the atmosphere, tension and little details that made this one stay with you.
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01 / THE STORY
Tess McGill is an ambitious secretary with a unique approach for climbing the ladder to success. When her classy, but villainous boss breaks a leg skiing, Tess takes over her office, her apartment and even her wardrobe. She creates a deal with a handsome investment banker that will either take her to the top, or finish her off for good.
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02 / FACES IN THE FRAME

Tess McGill

Katharine Parker

Jack Trainer

Oren Trask

Personnel Director

Tim Draper

Lutz

Tess' Friend