Watch How Do I Love Thee? (1965) Official Trailer

Jan and Penny are college roommates who disagree about what is appropriate dating behavior. Penny feels that Jan is a prude for not getting into the swing of the changing attitudes of the "second half of the 20th Century." Responding to the topic of petting, Jan says, "Why you make it sound as harmless as an extracurricular activity." One day Keith introduces himself to Jan in the library by helping her find a poem for their English literature class, and then asking her out to discuss it later. They hit it off immediately, and start enjoying sporting events, dancing, and studying together. Soon Jan is wearing Keith's frat pin. However, Keith's roommate Stan tells him that "Love has gotta include sex" and Penny is telling Jan the same thing. When Keith tips in this other direction one evening, Jan is hurt and will not go down this new path. Happiness lies along only one of the paths, and either Jan or Penny will soon find that their actions have brought regretful sorrow.