Matthew Logelin faces an unimaginable tragedy when his wife, Liz, passes away unexpectedly following an early caesarean section delivery of their daughter, Maddy. During her funeral, he is surrounded by his loving best friends Jordan (LilRel Howery) and Oscar (Anthony Carrigan), along with his mother Anna (Thedra Porter), and Liz's parents, Marion (Alfre Woodard) and Mike (Frankie Faison). Suddenly thrust into the role of a single father, Matt must navigate the challenges of raising his infant daughter alone.
In the initial months, the struggle to care for Maddy is overwhelming, especially after both Anna and Liz's parents leave. However, Matt perseveres, finding a way to raise Maddy on his own. As the years pass, Maddy, now around five years old, starts attending a private school.
One day, while at a park for a birthday party, Matt crosses paths with a woman named Swan (DeWanda Wise), who is introduced to him by Oscar and Rose, hoping to spark a connection. Matt and Swan hit it off, enjoying their time together, and soon he introduces Maddy to her, with both forming a lovely bond.
However, not everything goes smoothly. At school, Maddy faces ridicule from her peers over her outfit, leading her to bravely confront one of the boys, resulting in an injury that requires stitches. Panic sets in for Matt when he learns about Maddy's fall. He rushes to the hospital, a place he is hesitant to return to since it holds traumatic memories of Liz's passing. Ultimately, Matt allows the doctors to treat Maddy, feeling guilty for not being there for her. This incident drives him to end his budding relationship with Swan, as he worries he’s not doing enough as a father.
Amidst this turmoil, Matt’s boss, Howard (Paul Reiser), informs him of a job opportunity in Croatia, prompting Matt to send Maddy to spend time with her grandparents. However, he soon realizes that they want Maddy to stay with them indefinitely. Faced with the harsh reality of potential separation, Matt wrestles with thoughts of inadequacy, fearing he cannot provide her the happiness she deserves. After a heartfelt conversation with his sleeping daughter, he returns home to an empty space, grappling with his choice.
When Howard announces his retirement and suggests Matt take on his old role, Matt feels a pang of gratitude mixed with sorrow, knowing this could mean fewer opportunities to see Maddy. With help from friends Jordan and Oscar, he tries to cope, but loneliness grows as he searches for comfort.
In a touching moment of realization, Matt uncovers Liz's necklace, which Maddy had been longing for. As he heads towards the airport with Oscar, thoughts of Maddy flood his mind, compelling him to abandon the trip and return to her side. Their reunion is filled with warmth as she embraces him tightly, and he presents her the long-missed necklace.
As Matt bids farewell to Marion and Mike, emotions run high, particularly for Marion, who reflects on how much happiness Matt brought into Liz's life. He and Maddy head back to Swan’s place, where he offers an apology, and to his relief, she readily accepts, agreeing to join them for some ice cream.
In a lighthearted closing, Matt accompanies Maddy back to school, proudly donning a skirt to support her as they introduce a more relaxed dress code allowing jeans. This gesture symbolizes the lengths he will go to ensure Maddy feels happy and loved.
