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Cheng You-Ching (Ariel Lin) is the manager of a Taiwanese shoe manufacturer. On her 30th birthday, Cheng You-Ching receives an email on "the symptoms of premature aging" from Lee Ta-Jen (Bo-lin Chen), her best friend who she has known since high school. Unable to accept that he is like a bottle of fine wine that will get better with age and she is like a grape that will dry into a raisin as years go by, she agrees to a bet with Ta-Jen to see who will get married first before they turn 35. So they start to look for their potential lovers. However, Ta-Jen often says the girls he date are not a match for him and at the same time, he is not satisfied with the boys You-Ching dates. After Ta-Jen's relationship with his colleague, Maggie, he admits to Maggie that he has been in love with You-Ching the whole time. But there is a coincidence that when You-Ching is single, Ta-Jen has a girlfriend; while Ta-Jen break up with his girlfriend, You-Ching has reconciled with her ex-boyfriend. So Ta-Jen is always missing the opportunity to tell You-Ching his true feelings. As Cheng You-Ching looks around for a potential husband, she discovers that she was surrounded by unacceptable candidates. The only man who could love her despite her ill temper and stubbornness is her best friend. The only problem with this pairing is their extensive friendship.