Two stories. First story is about a hairdresser who's popular with the ladies but is rude, expressionless, and tactless. A makeup artist tries to fix his attitude by befriending him and teaching him how to be a decent person. Second story is about the insecure older brother of the hairdresser. He was always compared to his younger brother who was always great at everything so he developed a huge inferiority complex. A clumsy coworker then confesses his like for him and they start going out but his insecurities get the best of him.
I really liked the second story. It was so heartbreaking for the big brother to feel so insecure no matter what successes he's accomplished.
Sayonara, Itoshi No My Friend