Content Warning: This section of the guide includes discussion of illness and sexual content.

The novel uses the love triangle romance trope to explore the possible complications of navigating friendship and romance. Ridge Lawson, Sydney Blake, and Maggie Carson have been involved in a love triangle throughout Hoover’s Maybe Someday Series. In Maybe Now, the characters begin to set boundaries in their relationships in order to establish a healthier dynamic.

As Ridge and Maggie transition their six-year romance into friendship and Ridge and Sydney transition their one-year friendship into romance, new conflicts arise between them. Ridge doesn’t want “to walk away from Maggie completely, knowing she has no one else,” but he worries that Sydney might “put [him] in a position to choose between her happiness and Maggie’s health” (129). Meanwhile, Sydney worries that Ridge’s constant concern for Maggie’s well-being is evidence that he still has feelings for her; at the same time, she knows that she’d be worried if Ridge suddenly cut Maggie out of his life, given her medical needs. Maggie feels similarly trapped between Ridge’s, Sydney’s, and her own competing feelings and needs.