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Three women, six men, one very messy pregnancy—Asian rom-com chaos at its finest.
TMDB
60
IMDb
72

When I Fall in Love... with Both (2000)

messy love triangle supremacy90s/2000s city romancesoap opera energy

Overview

DramaRomance

From Singapore to Hong Kong to Macau, 3 different women with different lives experience the same situation of falling in love with 2 men and how they deal with the dilemma. In Singapore, meet Joy who's torn between her boss and an idealistic baker. In Hong Kong, Cherry dreams of the strong, macho type but also wants the sweet, sensitive New-Age guy. In Macau, Cecilia and Chun-Nam have been an item since high school. The passion dies, as it always does, and while working in Macau, Cecilia meets old schoolmate Tung. One night, Cecilia sleeps with both Chun-Nam and Tung, and gets pregnant.

Flag of HKHKCantonese
Content warning

Standout Aspects

Acting

Fann Wong's comedic timing saves Singapore segment.

Costume

Peak Y2K fashion across three glittering cities.

Writing

The pregnancy twist that ties all three stories.

Best for:Streaming: Late-night nostalgia trip with wine and judgment.·Friends: Yelling at characters together is mandatory.·Rewatch: Spot which guy you'd pick differently now.
Heads up:Sexual Content: Affairs, infidelity, and one very complicated conception.
Samson Chiu Leung-Chun

Director

Samson Chiu Leung-Chun

ReleasedMar 20, 2000
Runtime1h 55m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium

Top Cast

Michele Reis

Michele Reis

Cecilia / Xixi

Theresa Lee Yee-Hung

Theresa Lee Yee-Hung

Cherry

Fann Wong

Fann Wong

Joy / Lele

Peter Ho

Peter Ho

Sam Ho

Alex Fong Chung-Sun

Alex Fong Chung-Sun

Nam / Zhen-nan

David Wu

David Wu

Tung / A-Dong

James Lye

James Lye

Chi Sing / Zhi Xing

James Chen

James Chen

Zhi Wu

Sean Chan

Sean Chan

Zhi Wen

Law Kar-Ying

Law Kar-Ying

Joe Cheung Tung-Cho

Joe Cheung Tung-Cho

Ask about When I Fall in Love... with Both

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Deep Dive

Trivia, insights & behind the scenes

Cultural

This was part of a brief boom in pan-Asian co-productions aimed at Mandarin-speaking markets across Singapore, Hong Kong, and Taiwan.

Trivia

Michele Reis reportedly took the Macau role specifically because Cecilia's moral complexity was rare for Chinese cinema heroines at the time.

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