Ugly Me (2006) on Netflix

A beautiful woman (Mori) decides to transform into an ugly duckling in an attempt to ward off men and avoid more romantic disappointments.

In Santiago, Chile, the efficient architect Amanda finds that her boyfriend Pepe is cheating on her with her friend Fernanda. Amanda threats them both with a shotgun, but is arrested and loses her job. She travels to Valparaiso and decides to disguise as an ugly woman married with children to earn respect of men. Amanda is hired by Max to work at his company with the chauvinist Marcelo; the dedicated but limited family man Guillermo; and the ambitious just graduated architect Karen. Soon she proves to be very efficient and decides to give a lesson to Marcelo, seducing him posing as the sexy Helena. Meanwhile Marcelo gets closer to Amanda, who becomes his best female friend and advisor. When Helena humiliates Marcelo, he changes his behavior and starts falling for Amanda. And she also falls for him, but she is behind the eight ball with the situation she has created. Meanwhile Karen hits on Marcelo, who is now emotionally vulnerable.

—Claudio Carvalho, Rio de Janeiro, Brazil

When Amanda is humiliated by her lover and fired from her job, she decides to move to a new town and start over, but this time by making herself up as an ugly woman in an effort to be taken seriously. When she meets Marcelo, a cocky new co-worker and quintessential 'player', she decides to go one step further and test him by playing both her ugly persona and her real one (whom she now calls Helena) against him. But juggling a double life proves harder than she'd imagined, and when real feelings begin to develop between both Marcelo and Helena, as well as between Marcelo and Amanda, she finds her comedy of errors has turned into an odd and sexy love triangle.

—Marcelo Mitnik