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 ...