Apollo casts a warning in the sky to her sisters to trust no one before succumbing to her wounds. Lune attempts to finish her but is stopped by Nikaidō. Keima, Diana, Elsie and Haqua have Apollo taken to the Katsuragi household where they discover the magic dagger used on Apollo and Kanon is ancient Weiss magic and the culprits are Vintage, a group of demons who wish to resurrect the Weiss. With Kanon having a week to live, Keima must find the other four goddesses to heal her before Vintage gets them. To accomplish this without incident, Elsie disguises herself as Kanon and Keima tricks his mother to go to South America. Partnering with Haqua who is disguised as Elsie, Keima uses the rumor of Kanon's confession to see the reactions of his prior conquests, who will act jealous if they remember falling in love with him. Keima narrows his suspects to Ayumi, Chihiro, Shiori and Tsukiyo Kujyo, who were all embarrassed around him.

Keima confronts Elsie on why she’s still here and he still has the magic collar on his neck which the latter reveals that their contract is still not finish and the collar will only be removed until they capture all of the runaway spirits in the city. After meeting Keima’s mother, Mari, Elsie claims she is her “husband’s illegitimate child” which Mari snaps on her husband on the phone for his “infidelity” and allows Elsie to stay with them. Keima however, refuses to accept Elsie as his little sister as in his view, she doesn’t have the requirements that qualify her to be one which she tries to impress him albeit unsuccessfully. But upon hearing her story on wanting to be successful just like her older sister, Keima reluctantly accepts Elsie as his sister. During lunch at a popular food stall, Keima and Elsie find their next target, Mio Aoyama, a rich girl who proceeds to buy all of the yakisoba sandwiches. Keima believes she is an easy target as she has all the characteristics of a Tsundere, and a love confession might break her hard shell. However, the confession doesn’t work as planned, and Mio has her chauffeur beat Keima badly. As Keima and Elsie follow Mio to her home, they are surprised to learn Mio lives in a shabby apartment.

This episode features 4 different perspectives happening on the same day. Elsie is angry that Keima called her useless for making his lunch despite "it" having bizarre ingredients that are still alive. After her friend Chihiro advices her on how to impress Keima, Elsie decides to make a strawberry cake for him. Unfortunately, she mistakenly uses ingredients from hell instead of normal ones which causes many accidents including releasing a Mandragon and blowing up the Home economics class. At the same time, Keima irks the english teacher Kodama who dislikes the fact Keima constantly play games in class, yet still manages to get a perfect score on his test. After getting into an argument with Keima over games and real life at PE class, Kodama is chased by the Mandragon. Meanwhile, the Mandragon arrives at the Katsuragi's residence where it drops Elsie's cake. Keima returns home and finds Elsie's cake and eats it out of guilt but get hit on the head with a vase by his mother who mistaken him for a thief due to the Mandragon, which is eaten by the "lunch" Elsie made earlier which then chases after Kodama, forcing him to cancel his meeting with Mrs Katsuragi. Elsie returns home, vowing to make another cake for Keima but he reveals he has tasted her cake and doesn't like sweets much to her chargin.

Keima explains to the audience how he has captured fourteen girls and two unique girls after the last season. Meanwhile, Kanon is preparing for her school tests, but ends up talking with her split personality, Apollo, who claims to be a goddess. The next day, Keima and Elsie meet up with Tenri and within her, Diana. Diana wants Keima to marry Tenri as Tenri's love for Keima increases her powers, which he refuses. When asked to explain what she is, Diana reveals she is a goddess, one of the Jupiter Sisters, who helped the New Demons of Hell against the Weiss, when they attempted to take over the three realms of Earth, Heaven and Hell, and control all souls. After defeating them, the Jupiter Sisters sacrificed themselves by sealing themselves together with the Weiss, but they escaped ten years ago. Diana asks Keima to help find her sisters and reveals they reside in his past conquests, who did not forget their memories with him.

Keima plans to spend an hour each with the girls to raise their affection for him without any of them encountering each other with Haqua's help. He manages to succeed with Tsukiyo on the bus but compilations occur when the 2B-Pencils finish band practice early which leaves Haqua with Chihiro. As a result, he misses Yui but continues by walking home with Ayumi and Miyako. Unfortunately, Haqua and Chihiro are heading in the same direction which prompts him to take Ayumi and Miyako inside the mall. After making sure Chihiro is busy with Haqua, he has a private talk with Ayumi that he won't give up on her. Next, he meets up with Chihiro at the music store where he praises a song she wrote. Later, he heads towards the library to meet with Shiori where he finds a story written about them that resembles her conquest with the roles reversed but his character is killed due to the rumors with Kanon.

Keima arrives at the library whereupon Shiori allows him to read her story while being watched. Meanwhile, Nora discovers Kanon and demands Haqua an explanation. In the library Keima discovers that Luna, Tsukiyo's doll, is Vulcanus who warns Keima never to approach Tsukiyo again. Attempting to stop Vulcanus from being discovered, he approaches Tsukiyo not realizing she is in fact truly Vulcanus controlling objects. With both Vulcanus and Tsukiyo mad at Keima for cheating on her, he makes Tsukiyo remember the promise he made to her. Succumbing to her pity for his injury, Tsukiyo kisses Keima whereupon she grows wings. Nora explains to Haqua that Vintage have infiltrated the spirit hunters and the search order for the goddesses is a plot to capture them. Reunited, Diana and Vulcanus combined their powers to removes the cursed dagger but Apollo turns Kanon's body into a liquid state as a preservation measure.

Keima sends Tsukiyo home warning Vulcanus not to reveal herself while he searches for the other goddesses. Unexpectedly, Yui has come to Keima's home to ask him out. Keima explains to Haqua he must now conquer Yui before Vintage realizes she has a goddess. The next day, Keima crossdress as a girl which gains Yui interest to awaken her past memories while unknowingly being overseen by Shiori. After Keima asks her out for a date, the goddess Mars finally awakens inside of Yui. As the crossdressing couple spend time together on their date at an amusement park, Keima is kidnapped by a Vintage agent. Wishing to save Keima, Yui's love for him finally restores Mars' powers which she defeats the agent who is revealed to be Haqua which was a part of Keima's plan to awaken her powers. Yui proclaims her love for Keima and kisses him, which restore Mars' wings.

Keima gets sick from a cold so Nora's partner Ryo is ordered to watch over him. With two targets left, Keima decides to use his cold to get Ayumi to visit him by calling her while he calls Chihiro not to come so both of them won't visit at the same time. At his home, Ayumi decides to stay to take care of Keima after seeing him sick. Just when things were going according to his plan, Chihiro unexpectedly visits no thanks to Ryo letting her in. With no choice, Keima hides Ayumi under his bed as Chihiro takes care of him while trying to simultaneously raise both girls affection. After Chihiro leaves the bedroom after singing her song for him, Keima tries to explain to an angry Ayumi nothing is going on between him and Chihiro. But Chihiro knocks on the door and confesses to Keima which he feigns ignorance before she leaves. Keima tries to call Chihiro but Ayumi contacts her first where she admits she heard Chihiro's confession and supports her.

Ayumi is still angry with Keima but is forced to work with him after he becomes the 2-B Class Cafe barista. Keima tries to talk with Ayumi but her anger and Chihiro being there doesn't help. Meanwhile, Lune orders Vintage to target all of Keima's past conquests.

As Ayumi contemplates on what Keima said to her, Keima ask her to meet him at Kozue River. Haqua explains to Chihiro why Keima has to make Ayumi fall in love with him as he tries to make her like him again. However, their date is constantly interrupted by Vintage which Chihiro suggests she, Keima and Ayumi stay at Miyako's home.

Shiori is having trouble finishing her novel for the Mai High Festival due to her conflicting feelings for Keima. She then notices a young girl, who is actually her goddess, and chases after only to meet up with a crossdressing Keima. As she inquires his crossdressing and eat at a Ramen shop, Shiori tells Keima that she wants to make a story of him. Keima explains to Haqua that with Shiori's boosted confidence after their talk, she can now finish writing her novel. But the next day, Shiori is suffering writer's block so Keima decides to stay with her at the library to help her. After several drafts and procrastination by reading books, Keima eventually tells Shiori to write about herself especially when they both lock themselves in the library. Realizing Keima was there and kissed her during that time, Shiori starts writing. The next morning, Keima reads her story about her life at the library which ends with her declaring she loves Keima.

While attending a meeting between the section chiefs in New Hell, Haqua questions Dokuro Skull if Vintage have infiltrated the spirit hunters which the latter denies. However, Haqua is arrested by Public Safety which she later learns to her shock from Nora that Vintage have also infiltrated the highers ups and Dokuro Skull was the one who ordered her arrest. Back at Earth, Keima gathers all the awakened goddesses at his house in order to undo the spell casted on Kanon and awaken Apollo. During the ritual, Keima is brought to Apollo's realm. There, Apollo reveals she cannot leave now as she stopping the power of the Weiss from spreading the city but can only do so for three more days. Kanon and Apollo put their faith on him and grow their wings before he returns back home. While Majima High prepares for their upcoming festival, Ayumi becomes a participant of a pageant as Chihiro invites Keima on a date.

Chihiro and Keima head to the rooftop to continue their date. As they are about to kiss, Chihiro asks him to be gentle as this is her first time, which leads Keima to realize that Chihiro doesn't have a goddess as she does not remember her first kiss with him.

As they head to Ayumi's location, Chihiro tells Keima he should tell the truth to Ayumi as unknown to Keima, she already told Ayumi that he was trying to win her heart for something important. At the harbor, Keima tell Ayumi he will honestly tell the truth if she ask anything before continuing their wedding.

Keima attempts to finish and get the heroine, Sora Asuka from the PFP Bishōjo game "Crayon". But the game has many bugs including one that loops a previous scene over and over again. No making things any better is the fact saving the game only crashes it and game company that made it is now bankrupt thus there are no patches to fix the game. In order to avoid the bug loop and finish the game, Keima forcefully enlists a reluctant Elsie to help record the choices that he made in the game. Elsie is at first confused on why Keima takes the game seriously but soon respect his dedication to help the girls in his games just like the girls he helps in real life. After many attempts, Keima finally manages to avoid the loop bug and goes to the next scene but unexpectedly gets into another bug, resolving him to try again much to Elsie's horror. A wikipedia article about "Crayon" reveals a rumor that someone managed to get the ending, hinting Keima was able to finish the game.

Keima and Elsie realized that Kanon is actually turning invisible because of the spirit inside of her and he manages to stop Kanon from tazing him again by praising her song. As Keima sends Elsie to investigate, they learn Kanon was once a member of the pop idol group Citron before they disbanded and has never played any songs from her old band and Kanon's need for attention was the result of people not noticing her in the past. Keima later receive an email form Kanon and cheers up the depressed Kanon at her TV shoot. Kanon continues sending Keima an obsessive number of emails to visit her whenever she feels depressed. With the relationship going smoothly, Keima agrees to come to Kanon's Christmas Eve concert at Narusawa Seaside Hall. On the day of the concert, Kanon is nowhere to be found and Keima know it's time to go to the final stage of his plan.

Kusunoki is embarrassed on her date with Keima but still continues it hoping it will draw her feminine side out. After failing to connect themselves in their date, Kusonoki and Keima decide to do the most romantic thing: eating an ice cream together. After overcoming their embarrassments and eating it, Kusunoki's feminine side finally comes out where both Kusunoki and her feminine side fight for dominance. As both of them fight and explaining their reason with Kusunoki wanting to get rid of her femininity as it is a weakness in her martial arts and preventing her from inheriting her family dojo while Feminine Kusunoki wants to get rid of her martial arts as its preventing her from becoming a woman, Keima stops them and tells them they can just choose both and not sacrifice one for the other. Kusunoki protest at first but Feminine Kusunoki tells the former that Keima is correct since she did enjoyed her date with Keima despite her earlier denial. Feminine Kusunoki admits her defeat but makes Kusunoki promise not to forget her femininity. As her last act, Feminine Kusunoki takes control of Kusunoki's body to kiss Keima as a remembrance which Kusunoki does so willingly a she realize she likes Keima and kisses him which release the spirit inside of her. Kusunoki still continues her marital arts and now accepts her femininity. Later, Elsie tries to explain to Keima the powers of the evil spirits only to get trapped inside a Spirit capturing bottle used by her friend and fellow Spirit hunter, Haqua.

Haqua arrives and tries to capture the spirit which has gotten powerful from feeding the negative emotions of the unconscious students around them but the spirit escapes to the roof by possessing the students to stop Haqua and Elsie. Keima suggests Haqua should team up with Elsie but Haqua refuses, claiming she is more better than her. However, Haqua is in distraught as she has failed to live up to her friends expectations which allows the spirit to possesses her. By the time Keima and Elsie reach the roof, Haqua is under the spirit's control and it uses her and the possessed students to capture them. In order free Haqua from the spirit's control, Keima tells Elsie to calm the negative emotions in Haqua's heart. As Elsie talks to her, Haqua admits to Elsie that she lied to her as she was ashamed and didn't want let her down but Elsie breaks free from the possessed students and hugs Haqua, telling her no matter what, she will always been the greatest demon in her eyes which finally breaks her free from the spirit's control. Now working together, Haqua defends Elsie from the possessed students while the later uses the spirit capturing bottle to capture the spirit which they succeed. With the spirit captured and returned to her, Haqua thanks Keima for his help and for not revealing her lie to Elsie while Keima congratulates Elsie on a good job which she celebrates by buying both Keima and Haqua lunch.

After learning there are still 60,000 spirits to be captured before his contract is finish, Keima goes into a depression, not helping matters when his classmate the cheerful Chihiro Kosaka makes fun of him. Despite telling Elsie he doesn't care what people say about him, he is still affected by Chihiro's words. Suddenly, Elsie detects a spirit and to Keima's horror, it's inside Chihiro. Keima refuses to help her since he's still angry on what she said and the fact she's very average and doesn't have any unique traits that can help him figure her out. However, they watch her confessing to a boy, only to see her get rejected and runaway crying. The next day, Keima, feeling sorry for Chihiro, decides to console her over her rejection but to his anger, Chihiro is back to her old self as she reveals she has been confessing and getting rejected to any boy she fancies many times. Keima scolds Chihiro for playing around with love but she strikes back with his obsession with games and his anti-social attitude which strikes a deep cord within him. Even more depressed, Keima locks himself in his room for days until he does come back to school but refusing to speak with anyone. Worried about him, Ayumi visits Keima who has fainted from not eating.

Ayumi attempts to lighten Keima's mood after his fight with Chihiro and asks him to makeup with her. After sharing lunch together, Keima learns that all his past girls he helped still have remnants of their feelings for him. Ayumi later tricks both Keima and Chihiro to do cleaning duty together where Keima learns Chihiro is truly sorry for insulting him. By chance, Keima discovers Chihiro's new crush, Yuta. After admitting Keima's claim that she doesn't take love seriously, Chihiro ask Keima to teach her some of his dating sim techniques in order to win over Yuta's heart. The following morning, Elsie indirectly points out that should Keima help Chihiro, he would not have to be directly involved in filling the emptiness in her heart. Overjoyed by this revelation, he gathers information on Yuta which he then formulates into a carefully calculated plan where he helps Chihiro get a notable impression from Yuta. As Keima teaches Chihiro in his final plan to get her to confess to Yuta, Chihiro start to take an interest with Keima.

As Keima prepares Chihiro to finally confess to Yuta, Chihiro begins to have second thoughts and realizes she likes Keima and calls off the confession. However Keima is angry that everything he did for her is being thrown away and accuses her for not being serious which Chihiro angrily leaves as it won't matter how serious she get as she'll never be special like others. Keima, after realizing he never consider Chihiro's feelings as he was too focus on the confession, he decides to make amends and capture Chihiro's heart. By the time he finds her on a ship, Chihiro confesses she started liking Keima since they're both similar of being disappointed with the real world. However, he corrects her that despite his dislike with the real world, he never given up on himself so she should she do the same thing. But when Chihiro tries protest that someone as average as her can never be special, Keima kisses her by surprise and tells her as long as she truly wants it, nothing can stop her from becoming special, which forces the spirit out. With the spirit gone, Chihiro becomes more cheerful and confident and tells Elsie they should start a rock band. As for Keima, he starts to question his life after remembering the girls he helped before.

Keima learns the rare First Edition of the Dating sim game "Love Tears" will be on sale at another town so he goes there the next morning with Elsie tagging along. After teaching Elsie the history of dating sims and difference between many editions of the same game, Keima tasks Elsie to buy the game while he goes to a game fair. When she finally finds it, she discover three different editions of the Love Tears game but manages to get the correct one due to it's expensive price. Unfortunately, Elsie instead buys the Love Tears anime by mistake which Keima suspected so he bought the game at the game fair just in case. Later, Haqua arrives at the Katsuragi residence's and asks Elsie and Keima's assistance for her report during the time she captured the escaped spirit at Majima Academy by using a magical scale model of the school including autonomous dolls of them and the students that follow their command by a mic. After Keima helps complete her report, he protests over one detail that Haqua changed in her report which was when they both arrived at the theater, she claims Keima clinged to her when the truth was it was the other way around. After they fight over their version of that incident, Haqua destroys the mic to keep Keima from changing it. Unfortunately, she last commanded that Keima was a pervert who chases her which Keima's doll does obscene things with Haqua's doll, much to Haqua's embarrassment and Elsie's anger where they both hit Keima and accidentally let the dolls loose. After helping recover the dolls, Haqua's thanks them for their help and Elsie wonders if Haqua used the report as an excuse to visit Keima.

Jun Nagase is an idealistic and upbeat new student teacher at Majima Academy assigned to her senior's class, Miss Nikaidō, Keima's teacher. Jun is at first bewildered that Keima is playing video games in class and nobody minds about it but after the teachers tell her the problems they have to deal with him, Jun believes Keima is a problem child and wants to help him. She goes to talk to him but gets scared looking into his eyes and leaves. Convinced that Keima is actually lonely, she resolves to help him open up which at the same time a spirit enters her body. When Keima and Elsie learns about Jun's spirit, Keima finds his next target difficult as making of a teacher falling in love in games takes too much time as teachers never fall in love with their students as they only see them as their students only. Thus in order to make Jun fall in love with him, he has to make Jun see him as her equal in a short amount of time. As Keima leaves school to figure out his plan, he is caught by Jun who thinks he's ditching school. After dragging him to have lunch with her and talking about her idol, the late pro wrestler Jumbo Tsuruma, Jun tell Keima to talk about his problems to her. However Keima does not like this unprecedent event since it will take too long for him to capture Jun's heart.

Keima has an idea to quickly grow the relationship between him and Jun by making her hate him and turning those feelings into love. But the plan backfires as it only cause Jun to be more concerned about him. After getting him alone in class, Jun tell Keima that she believes he is lonely and plays games as a form of escape but he shoots her down as she has no clue what he is and that she shouldn't judge him by her own standards, which leaves Jun shocked. With no other choice and a change of plans, Keima asks Miss Nikaidō for more information about Jun which she agree in exchange for helping her in her school work. Meanwhile, Jun still affected by Keima words, decides to help his class in their schoolwork after Mr Kodama insult them as failures. But when the students tell her that they don't have the zeal to improve themselves, Jun in anger, inadvertently scolds them and quickly leaves. After finishing his part of the deal, Nikaidō finally reveals to Keima that she and Jun were members of the highschool's girls basketball team before it disbanded over an incident in the past. With this new information, Keima now knows what to do.

Still upset over what happened at class, Jun goes to watch a pro wrestling match only to find Keima sitting at her seat thanks to Elsie making a copy of her ticket. As she is forced to sit with him to watch the match, Jun wonders why the class won't let her help them, which Keima then asks her why the girls basketball team disbanded when she was captain and correctly concludes that it was her idealism that forced the other members to quit and despite claiming she was trying to help the team for them, she was actually helping them for herself which Jun leaves the match in anger. Despite this, Keima concludes it's time to capture her heart. Later, Jun tells the class she has entered them for a marathon hoping to help them bond, but instead they refuse, feeling that she's trying too hard on them, which leaves Jun disappointed and tells the class how selfish they are before running away. As the class bad mouths Jun, Keima unexpectedly calls out on their behavior and disappearing before they confront him. As Jun arrives at the old girls basketball team locker room, Keima confronts her, telling her despite claiming to have changed in order to teach her idealism to others, she still hasn't changed at all. As she runs away into the school gym crying and wondering why people won't let them help her, Keima consoles and tells her to not give up and try harder as it will finally make them accept her idealism. Just then, the whole class arrive in the gym to apologize to Jun much to her joy. Unknown to Jun, Keima knew what was going to happen so he planned with Elsie to have the class to start hating him after Jun left and made them worry about her after she was gone. As Jun's time as a student teacher comes to an end, Keima sees her off and asks her to come back which she promises to become a better teacher and kisses him, finally expelling the spirit inside of her.