According to librarians, these 56 sad books will make you cry. Learn more about why these emotional picks are all must-reads.. true sad love stories that will make you cry Here are a few true sad love stories that will tug at your heartstrings and likely leave you in tears: Story of Mary and Jake Mary and Jake were high school sweethearts who had been together since they were 16. They were inseparable, and everyone around them thought they would end up married. However, Jake was diagnosed with a rare form of cancer.
From heartbreakingly beautiful memoirs to thought-provoking fictional stories, these sad books make us dissolve in a puddle of tears.. Read Maybe from the story Sad Short Stories That WILL! Make You Cry by OutOf_Love with 20,706 reads. shortstories, reallygood, crying. Cindy and Thomas were bo.