It's Mary-Kate's first Valentine's Day with a boyfriend and she is filled with Valentine's Day spirit. So much so that she decides to put an ad in the school paper and advertise herself as a singing telegram for White Oak and Harrington! She's having a great time sending Valentine's messages for her friends . . . until she gets a request to give a Valentine to her own boyfriend -- from someone else! Ashley isn't thinking about Valentine's Day. She got a bad grade on a science test and the only way she'll get an A on the next one is if she can convince the biggest nerd in the class to tutor her. He says he'll do it -- but only on one condition. Ashley has to turn him into a total stud in time for Valentine's Day so the girl of his dreams will go out with him. The problem? Nothing Ashley does seems to change him at all! And if she doesn't change him soon, she'll be out of luck for her next test!