Singing in the Rain is the 7th episode of the second season and the 19th episode in all.
The episode begins with Chihiro wanting to tell Keima something about the recent raining in Maijima but Keima suddenly stands up, and stated that Chihiro need to confess to the guy she likes (Yuta) tomorrow. After hearing that, Chihiro then showed a glimpse of sadness before agreeing while Elsie watches from afar.
At night while the sky still raining, at Chihiro's room, she is looking at "Guaranteed Success Places to Confess your Love ~School Edition~" book as she sighs and brings out her cell-phone before realizing that the phone needs to charge its batteries. She then looks out of window while the local news broadcast about the weather forecast through her TV, informs about tomorrow's long-awaited sunshine.
Meanwhile, at the Katsuragi household, Keima, after hearing the news, continues on preparing Chihiro's confession for tomorrow as he comments on how the rain's finally going to let up. Elsie then shows up, after having a bath and suggests that Keima should take one too which Keima responds by saying that he'll do it later. Elsie was then quite impressed with Keima's countless scenarios as Keima said that tomorrow's weather condition will improve on Chihiro's chances of success. Keima then proudly exclaimed that none of his strategies have ever failed. Elsie then sits beside him and comments on how hard-working Keima is and she was no longer worried. Keima then said that its still better having him to conquer Chihiro personally. He also was quite fascinated to realize that a huge portion of his galge knowledge can also be applied to males. Keima also comments that since Chihiro doesn't have much of a personality, he can easily insert her into a "player role".
After hearing that, Elsie got angry and said that Keima shouldn't be so mean towards Chihiro before stating that Chihiro also has some positive traits. When being asked by Keima on what, Elsie said that Chihiro is cheerful, optimistic and have a positive attitude, only to be told off by Keima that these three traits she stated are the same. Elsie then throws a tantrum arguing that Chihiro really have many good traits about her.
Later, Chihiro is seen confessing to a guy while raining. The person seem to rejected her and Chihiro was shown to be sad, but then she saw another person holding an umbrella waiting for her....
Chihiro woke up from her dream and checked her cellphone. Her cellphone received a new message from Keima (named as Otamega) telling her to get there on time. Seeing that, she then gets ready. On the way to school, she bought some nikuman.
Meanwhile at school, while Keima complains about Chihiro's half-hearted attitude, he orders Elsie to wear a fake mustache so that Chihiro could practice her confession.
As Keima was writing about Confession number 5, Chihiro appeared and gave Keima a Nikuman. Chihiro then told Keima that she seem no longer like Yuta anymore. This greatly angered Keima, since the others (conquest girls) gavealltheir efforts while Chihiro just slacks
all the way. Chihiro then explained that she cannot run fast like Ayumi or sing as good as Kanon, which mean she doesn't shine like them and thus there's no point to be serious as she walked away.
Elsie then returns and reports to Keima that she did not locate Chihiro only to see Keima dejected. Keima then replied to her that the confession failed. Keima then stated that he had being so engrossed with the guy, that he failed to notice Chihiro's feelings, he then said that Chihiro's emptiness may have increased due to him. Keima then runs off telling Elsie that he will take care of Chihiro himself, before stating to himself that he won't fail again. Keima and Elsie eventually reached to Maijima Seaside park and he quickly pushed Chihiro away believing the latter was about to commit suicide.
Keima then tells Chihiro that he's worried about her which made Chihiro blush at first but then she yells at him before admits that she knew that she's never been serious and for that she will forever be an average girl. Keima then said that she's struggling which she denied. Keima responds by asking why would she chase after boys she don't really like in the first place. Chihiro then quells down and says that she had admired those who shine brightly and if she felt that if she stays close to them, she'll feel better. Keima without her notice stands besides her while Chihiro scolds him for intruding her space but Keima reminded her it's raining. She then said that she thought Keima would understand her since they are the same. Keima denied her comparison and explained that even though he is giving up on the real world, he never gave up on himself. Chihiro then said that there are limits in reality which stop people to become what they want. Keima denied her thought immediately. Keima then admits he has misjudged her personalities before he said that she's the only girl that has defeated him. Hearing that Chihiro then hits Keima with her umbrella.
Keima then grabbed onto Chihiro's hand and said that she can shine if she wants to. Despite Keima's constant encouragement, Chihiro still angrily said that she'll always be average. But before she could finished, Keima kissed her. Keima said that he'll always be there to help her as Chihiro's Spirit left and gets captured by Elsie.
The next day, Elsie was surprised that Chihiro decided on starting a band as Chihiro said that she will do it. Elsie then said that she cannot play any musical instruments, which Chihiro also admits that she cannot sing as well but she'll always believe in herself. Chihiro then recruits Elsie and gave her a research book on Mai-High's hottest guys. Elsie then misunderstood Chihiro's words that her life is now an accompaniment to Chihiro as the scenes of Chihiro leading a much more happier life is showed.
Back to school, Elsie said that although there are plenty of mishaps, it is good that everything worked out in the end. But Keima declared that the real world defies all logic and his PFP got wet and how it is really a crappy game.
In the last scene, Keima realized that despite everyone struggles against reality, they will eventually overcome it. He then wonders what about him and what's going to wait for him tomorrow......
When Elsie pouts, she turns in what might be a parody on the American TV show, South Park, and its art style.