Maybe Someday by Colleen Hoover chronicles the turbulent relationship between Sydney Blake and Ridge Lawson. Published in 2014, Maybe Someday is the first book in the Maybe Someday series, which features three books. Maybe Not follows Maybe Someday and documents the uncanny origins of the relationship between Warren and Bridgette. Maybe Now is a sequel to Maybe Someday and continues to follow Ridge and Sydney’s story. Written from the alternating perspectives of Sydney and Ridge, Maybe Someday explores the complexities of infidelity, disability, and passion.

This guide was written using the Simon & Schuster eBook edition of Maybe Someday.   

Plot Summary

A prologue details the aftermath of Sydney Blake’s discovery of her boyfriend Hunter’s affair with her roommate Tori. Outside in the rain, Sydney struggles to decide where to go after she flees her apartment. She reluctantly agrees to her neighbor Ridge’s invitation to stay in his apartment despite her anger over Ridge’s delay in exposing the affair to her.

Two weeks earlier, Sydney listens to Ridge playing guitar from across their apartment courtyard. Experiencing writer’s block, Ridge asks Sydney for her number and requests she share the lyrics he witnessed her mouthing to his song from her balcony. Self-conscious, Sydney hesitates before sending her lyrics over. Impressed, Ridge shares her lyrics with his younger brother Brennan, the lead singer of their band Sounds of Cedar, and they agree to employ Sydney as a songwriter. Aware of Hunter and Tori’s affair, Ridge decides not to tell Sydney the truth.

A week later, Ridge finally tells Sydney how impressed he was with her lyrics and asks her to send him more. Sydney obliges. As Sydney and Ridge continue to communicate via text message, he grows conflicted over his decision not to tell Sydney about Hunter’s infidelity. On her 22nd birthday, he decides to disclose the truth.

Chapter 4 returns to the present. Sydney moves into Ridge’s apartment and learns that Ridge is deaf. They continue to communicate over text message. Desperate not to be alone in her heartbreak, Sydney asks Ridge if they can hang out as a distraction. They begin to write songs together. As they grow closer, Ridge divulges personal information about his past while Sydney begins to develop a deeper attraction to Ridge. To aid their songwriting, Ridge and Sydney engage in close physical contact. Ridge feels Sydney’s heartbeat as she sings, and he plays the guitar. One night, they fall asleep as they embrace. Awakened by knocking on the door, Ridge pushes Sydney into a bathroom and confesses that he has a girlfriend of five years named Maggie. Ridge’s childhood best friend and band manager Warren questions Ridge about his relationship with Sydney, but Ridge brushes off his concerns.

Later that evening, Maggie arrives for a visit and invites Sydney out to a club to celebrate her birthday. Throughout the evening, Sydney feels conflicted over her jealousy of Maggie and notices Ridge’s jealousy over her friendship with Warren. As Warren and Maggie drink excessively, Ridge and Sydney share details about their pasts. Ridge explains his traumatic childhood as a child who was deaf with parents with substance use disorders, and how he was shamed for his speaking voice. Sydney explains her father’s disapproval with her decision to pursue music education and her financial independence. Once again, Ridge and Sydney fall asleep together and are awakened by Warren.

Weeks later, Ridge and Sydney reunite to work on a song together, which they title “Maybe Someday.” In the song, Ridge and Sydney express their desire for one another and their hope to be together someday. Later, as they listen to a rough cut of the song provided by Brennan, they share a passionate kiss. The next day, Sydney and Ridge attempt to navigate their guilt. They write long messages to each other that convey their mutual decision not to act on their feelings.

As friends, Sydney and Ridge continue to work on music together. The lyrics of their songs express their feelings for each other and their struggles with temptation. Through the songwriting process, they continue to share intimate moments as their attraction grows. As they prepare for Warren’s birthday party, Ridge finds himself sharing details about his childhood that he has never shared with Maggie. At the party, Sydney becomes intoxicated to ease her anxiety. A drunken Maggie attempts to help Sydney. Eventually, Ridge forces both women to go to bed and cares for them throughout the night.

As he cares for Sydney, Ridge becomes overwhelmed with guilt and writes on Sydney’s hand a request for her to move out of the apartment. Before Sydney can read the message, she wakes the next morning, decides to move out on her own, and discovers Maggie unconscious in the bathroom. Warren calls an ambulance and informs Sydney that Maggie has cystic fibrosis-related diabetes, which shortens her lifespan considerably. After following Warren and Ridge to the hospital, Sydney finally reads Ridge’s message on her palm.

As she recovers in the hospital, Ridge attempts to convince Maggie to move in with him, but she refuses and asserts her need for independence. Back at the apartment, Warren tells Sydney the origins of Ridge and Maggie’s relationship and Ridge’s unwavering devotion to protecting Maggie. He comforts Sydney and aids her in her search for an apartment of her own. Ridge returns to the apartment to say goodbye to Sydney. He speaks for the first time in 15 years to express his deep feelings for her. A text message from Maggie interrupts this intimate moment and reveals that Maggie has discovered the truth about Sydney and Ridge’s kiss from weeks earlier. Ridge rushes off to find Maggie, but she avoids him and, in a note, asks him to give her space.

Sydney moves out of the apartment. Ridge reaches out to Maggie and travels to San Antonio to reconcile. Instead, Maggie breaks up with Ridge because of her need for independence. Three weeks later, Ridge begs Warren to share Sydney’s address, and visits Sydney at her new apartment. They share a passionate kiss, but Sydney resists Ridge’s efforts to begin a relationship with her out of fear of his continued devotion to Maggie. In a letter, Ridge expresses his true feelings for Sydney and his lack of desire for Maggie. He does not push his desire to be with Sydney and offers to wait until she feels ready to begin a relationship.

Three months pass by. During this time, Ridge plans a show with Brennan and Warren. He begins writing music inspired by his love for Sydney. Warren convinces Sydney to attend the show without telling her about Ridge’s participation. At the show, Ridge plays his new music for Sydney and publicly displays his love for her. Through the music, he asks Sydney when they will be together. As a sign that she is ready, Sydney embraces and kisses Ridge. Back at her apartment, Sydney tells Ridge that she loves him in American Sign Language. The two have passionate sex.