Ernest Hemingway wrote to F. Scott Fitzgerald that “The good parts of a book may be only something a writer is lucky enough to overhear or it may be the wreck of his whole damn life — and one is as good as the other” (305). With that, I created a collection of short stories that analyzes my generation of women’s struggles. Framing the thesis are two stories involving three women, Lindsey, Jenny, and Sarah, “The Generation of Discontent” and “Revisions,” with the characters attempting to sort through love, success, and happiness in society. The piece “The Bachelor” has Amanda torn between her currently successful life and the glamour and sometimes infamy of being on ABC’s reality show The Bachelor. In “Eggs Kennedy Style,” the fine line between delusion and dreams becomes defined in both Nan and Kelley of being one of America’s royal Kennedy family. “Cops and Robbers” shows the inner turmoil of women who do not aspire to be mothers and feel guilty for their aspirations as well asthe resulting resentment when they have to give up their dreams. The ideas of taking your loved one for granted and life goals become the driving aspect of “Flat Tire” where story picks up in the middle of major fight between Nicole and Tommy stemming from him dropping the garter the night before at their friend’s wedding. “Almond Blossoms” between a flashback to Amsterdam with Sam’s Dutch fling Andric and present time suburban Ohio with her finance Kevin showing the conflict of being single compared to being settled. As Fitzgerald said, “An author ought to write for his generation” (ix) and I wrote based on my personal experiences as well as my friends’ tales and tribulations that tell of our generation’s struggle. Giving a voice to the high hopes and resulting discontent I feel is important which models the Modern writers like Fitzgerald’s Gatsby’s green lighted hope for Daisy. I hope to revive a bit of that Modern era in my time though our green light just might be the glow of The Bachelor from the television.