Cherish the Day - 1 ª Season

Evan takes his niece Esther to the library where he notices a woman named Gently James trying to avoid late fees for her boss, Miss Luma Langston, at the front desk. Though Evan offers to pay the late fees, Gently insists it's not about the money, and he is impressed when Gently convinces the librarian to waive the fee. Later, Evan and Gently connect on social media, and they meet at a cheesecake shop. As they learn more about one another, Evan offers to help Gently run an errand to pick up a used refrigerator for Miss Luma. They pass the time at a nearby arcade while they wait for the owner to return, but their powerful connection takes a sharp turn when Evan says something that makes Gently feel judged. They finally arrive to pick up the refrigerator, but they once again disagree about how to solve an issue. When the conversation escalates, they separate, feeling regret about the evening.

A year after their first date, fate brings Evan and Gently back together when they meet at an art gallery. The chance meeting turns into a wild date night that ends in the hospital.

It's three months into Gently and Evan's relationship, and Evan invites Gently to his parents' anniversary party. Just as Gently reluctantly agrees, she receives a concerning text about her mother. Later, at the anniversary party, Evan and his mother have a heated exchange about Gently. Gently is thrilled that Evan stands up for her, and they express their love for one another.

A year and a half after the start of Evan and Gently's relationship, Evan consults with both Ben and Miss Luma to plan a romantic getaway for Gently. However, Gently ends up surprising Evan in a move that could re-chart the couple's course forever.

Evan takes a day away from his new tech company to help Gently make as many wedding decisions as possible, but they soon realize they have wildly different expectations for their big day.