When Does "Always Be My Maybe" (2019) Take Place?
"Always Be My Maybe" is a romantic comedy film written by Ali Wong with Randall Park and Michael Golamco that released May 29th, 2019. So when is "Always Be My Maybe" set?
It takes place in the year:
We know this because right at the beginning of the main action we see Sasha Tran's "2019" award "FOR THE CATEGORY OF EXCELLENCE IN CUISINE" though the award does read "03/04/18" above "DATE". So it must be after March of 2018 AD.

2019 AD
We know this because right at the beginning of the main action we see Sasha Tran's "2019" award "FOR THE CATEGORY OF EXCELLENCE IN CUISINE" though the award does read "03/04/18" above "DATE". So it must be after March of 2018 AD.
More specifically, the new award Sasha wins at the end is clearly labeled the "2019 VISIONARY OF THE YEAR" award.
Specifically, the flyer for Marcus Kim's band Hello Peril's concert that Sasha attends about one-quarter into the narrative reads "Friday,May10" so we begin in May of 2019 AD.
Later, almost halfway through a different flyer is seen for the "Cherry Blossom Festival" at which Hello Peril either has performed at or will later perform and it reads "SAT JUNE 1- 2019". So the story continues to during or after June of 2019 AD.
Furthermore, the main action begins with a time and place setting subtitle reading "Los Angeles, 2019".
Additionally, the story begins with sequence that includes a time and place setting subtitle that reads: "San Francisco 1996". Sasha watches the television show "Clarissa Explains it All" (1991) on TV and it debuted on March 23rd, 1991 AD. Presumably it is 1996 AD.
Very soon after, there is a time jump and a time setting subtitle of its own reading "2003". In this segment Sasha sings along to ? on the radio. Presumably, it is 2003 AD.
Furthermore, the movie opens with a visual timeline of the characters at various ages that rolls backwards from "2019" to "2003" then "1999" and finally to "1996".
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