Concerned her widowed mother Tracy will be lonely when she leaves for college, kind-natured Ashley secretly creates an online dating profile for her mom and meets Jared, who seems like the perfect match. When Tracy "accidentally" meets Jared and they fall in love, Ashley is comforted to see her mother happy until Jared moves in and begins doing whatever he can do to shut her out of their new life. It quickly becomes apparent that Jared's hold on Tracy will lead to devastating consequences if Ashley doesn't do something about it and must find a way to take Jared down.

College student Sandy's new boyfriend meets all the criteria for a good partner according to her dad's best-selling dating handbook titled "Most Guys are Losers". However, when she brings him home to Chicago for Thanksgiving, her father thinks he knows better. His well-intentioned investigation into the new beau soon leads to awkward misunderstandings, spilled secrets and heartwarming moments.

The summer before college, Auden meets the mysterious Eli, a fellow insomniac. While the seaside town of Colby sleeps, the two embark on nightly quests to help Auden experience the fun, carefree teen life she never knew she wanted.

Italian-American crime bosses Vito Genovese and Frank Costello run their respective families during the 20th century. In 1957, Genovese moves to assassinate Costello.