In Episode 7 of "Surely Tomorrow," Kyeong-do takes Ji-woo to his apartment, where the two share an intimate moment and spend the night together. The couple wakes up in each other's arms the next morning, with Ji-woo still wearing the same orange T-shirt. Ji-woo receives a call asking her to move her car, and Kyeong-do moves it for her. His mother spots him and wonders what he's up to, but doesn't confront him.
When Kyeong-do returns home, he hugs and teases Ji-woo, who forces him to take the day off. However, he refuses and asks her to go to work with her sister as planned the night before. At work, Kyeong-do notices that Doo-jin is not at his desk and goes looking for him. He finds Doo-jin at a café and confronts him about following the An Dae-hye drug case based on the call the actress made a few days earlier.
Doo-jin is shocked to discover that Kyeong-do and Ji-woo are back together. Kyeong-do continues to pester Doo-jin for answers but gets a call from Ji-yeon. She asks to meet Kyeong-do, who shows up at her office. There, Kyeong-do notices Secretary Yoo getting scolded by a senior employee.
As he waits for Ji-yeon, Kyeong-do asks Secretary Yoo to make him a hot americano. She makes the coffee and prepares another one for Ji-yeon. Kyeong-do ends up picking up the iced americano that Secretary Yoo laced with drugs. Secretary Yoo gets upset, which Kyeong-do finds odd. Meanwhile, Ji-yeon tells Kyeong-do about Min-woo's involvement in the article exposing Jin-eon and Da-hye's affair.
Ji-yeon informs Kyeong-do that Min-woo is attempting to sell the company, adding that she wishes to ensure Ji-woo is confident enough to run it. Ji-yeon expresses her concern that Ji-woo might break down after learning about her illness.
Kyeong-do is perplexed when he learns that Secretary Yoo was hired by Min-woo. He hastily packs up the iced americano he was drinking and takes it to be tested for drugs or additional medication. Kyeong-do requests the pharmacist to expedite the analysis, claiming it is for an article he is writing.
Meanwhile, Secretary Yoo meets with Min-woo in private and asks to be removed from his project of drugging Ji-yeon. He offers her a higher salary and requests that she continue her work.
That night, Kyeong-do buys flowers for Ji-woo but runs into his mother, Nam-sook. She asks if the flowers are for her and takes them. At home, Ji-woo and Kyeong-do share a pizza for dinner. He tells Ji-woo about the confiscated flowers, and she becomes jealous. Kyeong-do tries to calm her down by revealing that his mother took them.
Ji-woo is upset with him for teasing her, and the couple discusses the new press photos Ji-woo took to announce her new position at Jarim Apparel. Ji-woo asks Kyeong-do to take paparazzi-style photos of her instead and explains that she does not like being chauffeured around by strangers. Just then, Kyeong-do receives a call from Jeong-min, who asks them to meet at Woo-sik's house.
At Woo-sik's house, the group teases Kyeong-do and Ji-woo for getting back together once again.
There, Kyeong-do brings up how Se-young is his only loyal friend who visited him at his military service station. Woo-sik gets jealous and asks Se-young what she was up to. Se-young tells her husband that she met Kyeong-do back in 2009 on Ji-yeon's wedding day. A flashback shows Kyeong-do trading leaves with a fellow soldier to attend Ji-yeon's wedding, hoping to meet Ji-woo after their first breakup. Meanwhile, Se-young and Ji-woo talk about her getting back together with Kyeong-do.
Se-young tells Ji-woo that they both need closure and asks her to end things with Kyeong-do properly this time. At the wedding, Kyeong-do is denied entry without an invitation. He waits outside in the cold but is unable to meet Ji-woo. He decides to have drinks with his friends. Se-young does not tell Kyeong-do about her conversation with Ji-woo. Just then, Woo-sik confesses his feelings for Se-young, and the two decide to get married.
Ji-woo watches Kyeong-do drinking with the rest of his friends and leaves without talking to him. The next day, Ji-woo tries to meet Kyeong-do at his military station but is denied permission. After returning to base camp, Kyeong-do calls Se-young, asking if she was the woman who tried to meet him earlier that day. Se-young lies and tells Kyeong-do that it was her, saving him from feeling hurt as they talk about Woo-sik.
In the present day, Kyeong-do and Ji-woo are driving back to his apartment. The couple laughs and giggles, reminiscing about their past near run-ins. The next afternoon, Kyeong-do is having lunch with a friend when his mother calls, asking if he is coming over for dinner. Kyeong-do lies, saying he has a press conference to attend. Nam-sook and Han-soo talk about their son and wonder if he is dating again. She worries that Kyeong-do will be heartbroken if things go south this time as well.
That night, Ji-woo is with Ji-yeon, who is showing her younger sister the ropes around the company. Ji-yeon warns Ji-woo about Executive Director Choi and asks if she is okay with the press conference photos. Ji-woo and Ji-yeon chat about the photos when Kyeong-do calls. Ji-woo tries to act cool and asks him to call later but is shocked to see him waiting for her outside the Jarim office building.
On the drive to Ji-woo's apartment, Kyeong-do reveals that the real reason he picked her up from work is because of his previous run-in with Jin-eon.
Jin-eon tries to access Ji-woo's apartment, but is shocked to find that Kyeong-do has the new code. He wonders if Ji-woo leaked news of his affair to get back together with Kyeong-do, leaving behind a luxurious Cartier ring for her.
At the apartment, Ji-woo reads Jin-eon's note asking her to take him back. She tells Kyeong-do that she'll have to meet Jin-eon to return the expensive ring. Kyeong-do is upset, realizing it was Jin-eon's plan to coerce Ji-woo into speaking to him.
Kyeong-do ponders what he can do to make Ji-woo happy and comes up with a plan.
Kyeong-do is planning to propose to Ji-woo during their second relationship. He measures her ring finger and buys a minimalist ring. Unaware of this, Ji-woo leaves him without talking things out after his father's accident. Kyeong-do is shattered and throws the ring away, leading to his addiction.
Kyeong-do discusses the ring Jin-eon left with his friends, Woo-sik and Jeong-min, urging him to give Ji-woo something big and luxurious to compete with Jin-eon.
Outside Kyeong-do’s office, Ji-woo waits for him but runs into Manager Han-kyung. Han-kyung invites Ji-woo for tea and the two discuss Kyeong-do. The manager reveals that Kyeong-do gave up a lucrative offer to work in Chicago for Ji-woo’s sake, making her feel guilty. Han-kyung adds that Kyeong-do has turned down multiple offers in the past, all involving Ji-woo, and says that he always prioritizes her, which makes Ji-woo emotional.
Ji-woo and Kyeong-do walk back to her apartment. Ji-woo tells him that she had the ring delivered to Jin-eon instead of meeting him in person. Kyeong-do is relieved and promises to buy her a better ring in the future.
Ji-woo brings up her earlier conversation with Han-kyung and thanks him for prioritizing her. She says she's happy he's not going to Chicago and wonders if she's being selfish. Kyeong-do becomes emotional and is relieved by her honesty.
Ji-woo looks for her car keys while Kyeong-do waits for a text. When it arrives, he takes Ji-woo out, and she meets her childhood chauffeur, Mr. Kim. Ji-woo is surprised to see him and greets him warmly.
Kyeong-do feels accomplished after giving Ji-woo something she values more than luxury items. The episode ends with Mr. Kim picking Ji-woo up from the cold outside the base camp late that night, minutes before Kyeong-do arrives.
