Dame na Watashi ni Koishite Kudasai

From Dazzling Scans: The unemployed Shibata Michiko is betting everything she has on her romance with a younger man—literally. In order to keep him happy, she deprives herself of the things she wants and buys him expensive clothing and accessories. Since she's flat out broke, she needs to find a job before she starves to death and loses her young love interest. However, Michiko discovers that the boy was never interested in her romantically. Depressed at being dumped and after a series of unsuccessful interviews, she bumps into Kurosawa—an intimidating former boss she used to dislike.