Maggie Hardin, the dedicated director of business development and outreach for art and design students at The New School in New York City, finds herself yearning to become a mother. In her quest, she reconnects with a former college acquaintance, Guy Childers, a quirky math major turned pickle entrepreneur, to donate his sperm.
During her time at the university, Maggie crosses paths with John Harding, a "ficto-critical anthropologist" married to a tenured professor at Columbia University. Their chance meetings on campus lead John to confide in Maggie about his ambitious novel. This shared interest draws them closer as she begins reading his work, leading to regular discussions that spark a deep connection.
In an attempt to start her motherhood journey, Maggie plans to inseminate herself with Guy's sperm. However, her plans take an unexpected turn when John arrives unannounced, revealing his feelings for her and expressing his desire to be the father of her child.
Fast forward three years, and Maggie and John are happily married with a daughter named Lily. However, Maggie finds her career ambitions often sidelined as she juggles the responsibilities of raising Lily and two stepchildren, while also supporting John's writing endeavors. During a stroll with Lily, Maggie bumps into Guy, who mistakenly believes Lily to be his daughter. She gently clarifies that the child is actually John's.
At a book signing event, Maggie confronts Georgette, John's ex-wife, acknowledging her lingering feelings for him. Maggie, realizing she wants to rekindle their relationship, offers to help Georgette get back together with John. Initially hesitant, Georgette ultimately agrees to the plan.
With Maggie's support, Georgette persuades John to attend a conference in Canada, where sparks reignite between the former couple, culminating in a romantic encounter. Upon returning home, John confesses everything to Maggie, who selflessly tells him that he belongs with Georgette.
After an accidental discovery reveals Maggie's intentions to reunite him with Georgette through a drunken slip from one of Maggie's friends, John leaves Maggie and Lily, disappearing for a while. Concerned, Maggie seeks out Georgette, hoping to get updates about John, and ends up inviting Georgette and the children to stay with her.
While at Maggie's home, Georgette spends the day absorbed in John's novel. Later, she candidly critiques it before returning it to him in an unexpected form – a bag of ash. Realizing Georgette understands him better than he knows himself, John forgives her involvement in the scheme, and they reconcile.
As time goes on, the blended family enjoys ice skating together. To Maggie's surprise, Lily begins to recite numbers, a talent neither she nor John possesses. Just then, she spots Guy approaching the rink, a look of revelation dawning on her face, hinting at new possibilities ahead.