The second episode of "Surely Tomorrow" commences with the imposing figure of Han-kyung, Kyeong-do's boss, chastising him for his indiscretion in meeting Ji-woo so close to the office. She wields the threat of resignation over the mounting backlash from the article and presses him to safeguard Dongwoon Daily's reputation.
Meanwhile, Ji-woo's brother, Min-woo, shares lunch with his wife, their conversation punctuated by the ongoing controversy. Ji-yeon, quietly observant, wonders if Min-woo is the one who leaked Jin-eon's affair.
At work, Kyeong-do endures taunts about his supposed entanglement with Ji-woo. Even his mother brings it up that night, adding to his distress.
Ji-yeon meets Ji-woo and urgently implores her to lend a hand to Kyeong-do, but Ji-woo resists. Hyun-kyung calls Ji-yeon, agitated by the escalating scandal, and Ji-yeon endeavors to soothe her.
Kyeong-do goes for a run, still reeling from the article's impact. He visits Se-young, where Woo-sik is present, and they brainstorm potential solutions.
The following day, Se-young meets with Ji-woo and suggests a reunion among the five college friends. Ji-woo asks Se-young to take her to Kyeong-do's house. He is startled to see her and she deftly distracts him by evoking their past together.
A flashback transports us back to 2007, where we see Kyeong-do escorting Ji-woo to Se-young's house late at night, facilitating their bond with his friends. The next morning, Mr Kim informs Ji-woo that her parents will be away for weeks. She gleefully decides to stay there, and Kyeong-do packs up as well, their closeness growing over the weeks.
One day, he generously offers to buy her an outfit from JARIM, unaware that she is the heiress to the brand. Ji-woo cleverly conceals her identity, eager to maintain a relatable bond with her new friends. That night, under the influence of alcohol, she teases him playfully about the idea of having sex.
In the present moment, Ji-woo inquires if Kyeong-do is still wearing his beloved orange shirt, hinting at his longing for her presence. She refuses to lend a hand due to his blunt comment from their previous encounter. He apologizes for his words, and Ji-woo finally relents. Kyeong-do adds that she'll need to don specific outfits for Dongwoon Daily to feature the event in a major article.
Later that night, Ji-woo finds herself chuckling to herself about their reunion. Kyeong-do angrily tosses the shirt aside but retrieves it the next morning, symbolizing his unresolved feelings. Meanwhile, Ji-yeon shares an awkward lunch with Min-woo, claiming she doesn't want to marry him.
That evening, Kyeong-do's manager requests a group photo for the article. Kyeong-do visits his parents and searches for the poster of their play. His parents bring up the topic of marriage, prompting him to leave in a huff.
The next day, the five friends reunite. Kyeong-do is in awe, watching Ji-woo wear the brand he recommended. He suggests taking a quick photo to end the reunion as soon as possible. Se-young shows an old picture of the five together, before the play. The group teases Kyeong-do about his forgetting lines and crying on stage after Ji-woo left. Ji-woo looks surprised and asks Kyeong-do if it's true. He calls himself childish, dismissing his friends' memories. They take a group photo, but Kyeong-do gazes at Ji-woo as they stand on opposite ends.
Outside, Kyeong-do walks Ji-woo to her car and thanks her warmly. She informs him that she's leaving for the U.K. the following week. He wishes her well with a heavy heart.
Later, Woo-sik calls, revealing that Ji-woo took the play poster from his bag. At home, Ji-woo reads it and reflects on the revelation of Kyeong-do's emotional breakdown on stage, her heart filled with both sadness and admiration for his vulnerability.
The following day, Ji-yeon perused the reunion article with renewed interest, prompting her to reach out to Kyeong-do. That evening, she made a spontaneous visit to his family's laundromat, reliving the memory of his mother tenderly caring for his father in the ICU. Min-woo, worried about her sudden trip, could only marvel at her determination.
Later, Han-kyung treated Kyeong-do to a dinner date, teasing him about her decade-long pursuit while he remained entranced by Ji-woo. Kyeong-do's phone rang, and it was Ji-yeon calling. They met outside the laundromat, and she introduced herself, reminding him of their previous encounter when he was a student.
Ji-yeon revealed that she orchestrated the leaked photos of Ji-woo and Kyeong-do, driven by a desire to keep Ji-woo from leaving. She believed that only Kyeong-do could stop Ji-woo from departing. She explained that she suffered from Alzheimer's and wanted the family business to pass on to someone capable. Ji-yeon firmly believed that Ji-woo was the only person who could run it effectively.
The next day, as Ji-woo was about to depart at the airport, Kyeong-do rushed in and halted her. He took her luggage, and she chased after him, pleading with security guards to intervene.
An epilogue depicts the five friends posing for a photo before their play, with Ji-woo wearing the dress Kyeong-do had purchased and Kyeong-do donning the same orange shirt, symbolizing their enduring bond and the circularity of their relationships.
