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As Sam Wexler approaches his 30th birthday, he faces significant self-doubt and confusion as a struggling writer. Living in the bustling environment of New York City, he endures an endless stream of rejection letters, which deeply affects his confidence and passion for writing.

During a difficult phase in his life, Sam meets Rasheen, a spirited young foster child, on the subway. Their encounter sparks something in him, prompting Sam to offer Rasheen a temporary escape from the challenges of the foster care system, highlighting Sam's innate compassion.

Meanwhile, Annie is grappling with her own struggles, particularly her battle with alopecia, which leaves her self-conscious and searching for meaningful connections. Her journey underscores the theme of vulnerability in the quest for love and acceptance.

Sam's cousin, Mary Catherine, reveals her plans to leave New York for a job opportunity in Los Angeles. This news sends her into a personal crisis as she discovers she is pregnant, leading to feelings of self-doubt and uncertainty about her future.

Sam tries to return Rasheen to social services but is met with resistance. Rasheen expresses his desire to stay with Sam, revealing their growing bond and the transformative effect it has on both their lives, prompting Sam to reconsider his role as a temporary guardian.

Encouraged by Rasheen's attachment, Sam decides to adopt the boy, striving to create a stable environment for him. However, this decision leads Sam into the complex and often confusing legalities of adoption, putting him face-to-face with unexpected challenges.

In an unfortunate turn of events, Sam faces a humiliating arrest while navigating the adoption process. This incident serves as a critical wake-up call for him, forcing him to confront the realities of becoming a guardian and the responsibilities that come with it.

Determined to support Rasheen, Sam discovers the boy's hidden talent for drawing. He begins supplying him with various artistic materials, fostering Rasheen's creativity and providing him with a positive outlet amidst his tumultuous upbringing.

While dealing with the responsibilities of parenting Rasheen, Sam embarks on a complex romantic relationship with Mississippi, an aspiring singer. Their relationship becomes challenged by various misadventures, reflecting the difficulties of maintaining connections while facing personal challenges.

By the end of the story, Sam begins to recognize a newfound sense of purpose in his life. He learns to embrace his evolving relationships with Rasheen and Mississippi, discovering that these connections provide the stability and motivation he desperately needs.

As Sam navigates his role as a guardian and a partner, he confronts the uncertainties that come with these responsibilities. The film closes on a hopeful yet uncertain note, leaving viewers to ponder whether this newfound stability will withstand the challenges that lie ahead.