Hayate shops in a poverty district then experience his misfortune. The story goes back in the daily life at the Violet Mansion apartment, where Hayate and Hinagiku make an early morning preparation. Maria notices how Hayate can be so popular with the girls. The tenants; Chiharu, Kayura, and Ayumu leave for school as Nagi gets up late despite Hayate's actions to wake her when she's been trying her best to do better in life. Athena Tennousu (as Alice in child-form) barely stays awake. After school, Nagi attempts to play video games when they all should be studying for their final exam. Hayate continues his hard work preparing for tomorrow already then begins studying after midnight and Hinagiku comes to his room to tutor him, and he wakes up for just an hour of sleep and does the same early morning routine. Unfortunately, he discovers everyone is sick; except Ayumu until she fakes it. The next day, Hayate caught their cold but pretends he's fine to relieve Nagi’s worries. Ruka returns from Las Vegas and gives Hayate her album since her concert has finished. By the time Hakuou Academy's final exam starts Hayate arrives miserable due to constant errands along the way. He returns home and finds everyone has prepared dinner for him as a way of thanking him for his kindness.

Nagi is playing her fierce video games until Maria instantly unplugs the TV. One morning, Nagi inadvertently awakens early at the Sanzenin Mansion and discovers how the early mornings can be so delighted. She follows a scent of cooking and found Hayate in the kitchen. After eating breakfast, Nagi tries not to get sleepy by doing some exercise which isn’t easy for someone of her lifestyle. At Wataru Tachibana's video store, Nagi purposely rents an R-18 naked DVD mix with a stack of random ones; however, when she presenting it to Shiranui in her tree house Nagi found out she had grabbed an R-18 horror DVD by mistake. Ending up watching the whole film Nagi becomes terrified and begs Hayate to stay by her side all day until she’d fallen asleep, and Hayate whispers her a good dream that suppress her fears. Maria also watches the film and its déjà vu. Shifting back at the Violet Mansion, Nagi confined herself from going to school on a soggy day. Hayate tries to persuade Nagi by using advice to motivate her. Maria lends Nagi some money saying it represents life. This finally inspires Nagi to go to school together with Hayate admitting that morning days are interesting.

Having to sleep late again Athena (Alice) takes in some sunlight for refreshments. Hayate gave her some ringlet-shaped chocolate. Suddenly, a big dog approaches Athena then licks her. She demands Hayate to find its owner. While they search for the dog’s owner on the streets, Athena disciplines the dog. Fumi appears declaring the dog, Armageddon, is hers. Armageddon quickly tackles onto Fumi, just as they leave Athena signs she likes Armageddon, and Fumi responds he likes her too because of her ringlet-shaped hair. The next day, Wataru struggles with the pile of money that Sakuya had delivered to him in order to keep his business funded. Hayate and Saki offer to help deposit the money into the bank account regardless of Wataru's denial. Walking on the streets, Armageddon and Yukiji suddenly appear then the dog snatches the briefcase full of money and runs off. He shows Fumi the briefcase, freaking out, Fumi plans to hand it over to the police, but her friend Sharna Alamgir warns she would be considered a suspect. Meanwhile, Saki blames herself for losing the money, Hayate goes looking for the briefcase he found that Armageddon brought it to Athena, but finds the money inside the briefcase gone. Fumi and Sharna gather to help search for the money, then Hayate rushes to Tama to have him translate for Armageddon to know where the money is. Despite being insulted by the dog, Tama confirms the money been stolen by bandits. Tracking down their hideout, Yukiji beats up the bandits as Hayate and Wataru arrive to retrieve the money. With the money finally deposited Athena asks Wataru he should comfort Saki and so he does. Afterward, Nagi and Athena are left alone together for the day. They warm up some Nikuman to eat but overcooked it. Thinking what to do now, Linn the ghost priest mentions they should go find Hayate at the Café Donguri to have him make dinner for them. Accepting the idea, they head out, but along the way Nagi and Athena get lost since neither are familiar

The Saginomiya residents are curious to why they don't have a maid to support them in any way. So Hatsuho went to request Hayate to handing out flyers to recruit suitable maids use to overcome Isumi's weakness of smartphones. Fumi chose to be a maid candidate confident in her skills. In the end, both Isumi and her mother rejected Fumi because she did not meet the standards of understanding how to use smartphones. Nagi responds Isumi doesn't need a maid. At the Aizawa mansion, Chiharu as Haru is teaching Sakuya to be modest. In a flashback, the story goes on how Chiharu been hired to be Sakuya's maid. Makita & Kunieda reach agreement that Sakuya needs a maid by choosing one at her café. Sakuya asks Nagi why she hired Hayate as her butler in the first place; she replies that it was fate. In an arcade, Sakuya and Chiharu play virtual games together, and felt faith in her so she had Chiharu become her maid. Back in the present, Sakuya visits Nagi then discovers Chiharu there at the Violet Mansion. She drags Sakuya away and begs her to keep her maid identity a secret. They search for ideas to draw a manga, ditching Sakuya since she can't read manga. Isumi tries to help Sakuya to entertain herself. Sakuya hopes Nagi can still rely on her.

Feeling depressed because she isn't fragile, Hinagiku wishes Hayate to give her a shoulder massage, but is too embarrassed to ask him. Thinking how to get him to offer her a massage, Hinagiku uses a chance while studying with Hayate in the evening, but fails. The next day, Hinagiku reflects from the previous night. Athena reassures Hinagiku she try hinting Hayate again. Hinagiku receives a call from Hayate to meet at the Sanzenin Water Resort to deal with the troublesome Hakuou Three Amiga swimming in the artificial sea. Abruptly, their old foe Gilbert makes an appearance causing Hayate to beat him up. Gilbert provokes a 2v2 volleyball game challenge with the butler. Gilbert's partner is a new and improved Eight, and he chooses Hinagiku as Hayate's partner believing she is "fragile". Hinagiku pretends to be fragile for Hayate at the start of the game, which they didn't expect. Hayate apologizes to Hinagiku that with her on his side he thought he'd win the game. Her mood changes when Gilbert laughs at her flat-chest, and hits the ball hard at Eight. Successfully winning the game, Hinagiku shows her swimsuit, introducing herself as the student council president and declares that she will not lose. That night at dinner, Hayate comes over to offer Hinagiku a shoulder massage. Overjoyed with his answer, Hinagiku happily takes him up on his offer.

At Hakuou Academy, Risa discusses with Hayate about why people recently been calling them the "idiot trio". Izumi and Miki thrash out then start arguing together with Risa, they decided to find results on who's the smartest of the three by creating an interesting film. Hayate follows Izumi firmly to where she’s recording a plant growing, but accidentally kills it. Next, Miki shows them some eggs she’s waiting to be hatch; however, Hayate corrects her that unfertilized eggs will never hatch. Last, Risa presents a contraption that sets off balloons, but failed to notice them flying away without recording. In the end, it became clear to Hayate that the three are idiots. Thinking about yesterday, the trio are in session alone then again rather study on how to be popular. Hayate comes to check on them, and Risa tries to force him into doing something shameless to Izumi for the cute and blush research. Later, Izumi does cleaning duty as punishment for being careless of the paper that Yukiji gave her to take to the class. She puts on an embarrassing act using Miki's video camera until Shiranui scares her, and then Izumi heads home forgetting to delete the video. The episode ends showing Hayate has taken the memory card from the camera.

Ruka the idol is told from her manager Atsumari that she been booked to star in a bicycle commercial, telling her how lucky she is. Nagi, Hayate, and Maria are watching a recap of Ruka's concert on TV at the Violet Mansion. Ruka got the day off so she makes a surprise visit there and informs them her amazing opportunity. Tactlessly, she doesn't know how to 'ride' a bike so she intensely desires Hayate to teach her how since he’s a professional at bicycling. Ruka first practices in the yard but ruins Maria's garden. It soon gets dark, Chiharu suggest Ruka should try practicing on Hakuou Academy's grounds. Hayate strictly trains Ruka to ride a bike down a steep hill, that looks risky. He pushes her down the hill and catches her before she falls, hoping it would help overcome her fear of falling. At the end of the day, Ruka and Hayate start having fun using a squirt gun. Nagi asks Hayate if he can teach her how to ride a bike too but expects him to do it more kindly. Later, Hayate, Hinagiku, and the Hakuou Three Amiga, were invited to see Ruka’s next concert. Hayate receives an urgent call from Ruka and Atsumari depending him to act as a backup dancer in a maid outfit on the stage, also Ruka wishes for his service because she's in a stress. The concert begins with Ruka singing through willpower. Before her last song, Gilbert shows up and battles Hayate. The staff members mistakenly put Gilbert’s robot on the stage and goes on rampage. Hayate quickly kicks the robot off the stage, he dances with Ruka joyfully, and the concert was a success.

Astonish to gaining weight, Ayumu efforts to preserve her health. Following at Café Donguri, Hayate gives Ayumu some Nikuman he made, at that moment, she realize her constant consuming of Hayate's food is the reason she's gaining weight. She stops herself from eating, but just couldn't resist Hayate's generous offer. In a flashback, Ayumu remembers how everyone prepared a surprise birthday party for her. Hayate was baking cookies for her, Maria questions who else's birthdays does he know, answering he remembers everybody's. Nagi and Chiharu compromise they should throw a surprise party for Ayumu over at Café Donguri. Before they can start setting it up, Ayumu arrives already! As she attempts to remind them what "today" is, they try to avoid the question by feigning ignorance until she gives up. Ayumu finally leaves after part-time and everyone quickly prepares the party. Nagi calls for Ayumu's return, but she is too dismayed, so Nagi use a sympathetic manner to convince her. Ayumu comes back and they surprise her with the party, feeling overjoyed she jumps onto Nagi. Back in the present, Ayumu walks home with Hayate saying it's unsafe during the night, leaving Hokuto inaccuracy. They go to Shiomi high school, to pick up Ayumu's notebook that she forgot. Hayate thought if his parents hadn't sold him to the yakuza he probably would've accepted Ayumu's confession from before (Season 1 episode 12). As they leave, after defeating a monstrous thief, Ayumu decides she will do her best to lose weight.

Top of the Hakuou clock tower, Chiharu is doing a speech pattern when Aika caught her unguarded. Aika responds that side of her is cute. Chiharu believes there are others who are more unguarded than herself, as she hangs out with Nagi due to their common interest. Later, Chiharu decided a barbecue for the tenants, and she has Hayate give her grocery shopping assistance. She questions Hayate what would he do if a girl confesses to him; he gives a serious answer. Ruka arrives at the Violent Mansion as she accepted Chiharu’s invitation. Ruka asks Ayumu if Hayate would become her boyfriend even if it means kissing him, which irritates Ayumu. As Hayate and Chiharu return, he responds to Ruka and Ayumu that Chiharu asked him the same question, but they misunderstood it, then everyone celebrate for the barbecue. Kayura is eating the kebabs and making weird remarks. In a flashback, Hayate and Nagi remember when they first met Kayura (and pitching up a tent). After Kayura rented a room at the apartment, she enrolls as a transfer student at Hakuou Academy, so Hayate and Nagi gladly give her a tour around the campus until they reach the clock tower and Hayate casually shows them Hinagiku changing. Back in the present, after the barbecue and the tenants go to their rooms, Kayura states that you should not take your instant feelings too seriously. Hayate accidentally sees Hinagiku changing again; prompting that Hayate is the one who is most unguarded.

Shiori fixed a tape recorder for Yukiji then tells her days as a student at Hakuō Academy. 7 years ago, when Maria was the student council president, Shiori amazed how academic and cute Maria is, so she shows her camera photos of her growth…but Maria breaks it like it was an accident. In the end, it seems Maria refuses to expose any of her cute traits. At the Sanzenin Mansion, Maria discovers a love letter for Hayate; however, he wants to turn it down then Nagi returns a strict reply to the sender; a second later, the sender replies a horror letter to Hayate which now scares him. Nagi devises Hayate and Maria to go on a fake date in order to drive away the sender. The sender is revealed to be Linn and he gets enrage of seeing Hayate dating Maria. Hayate and Maria follow Nagi's script by trying on different clothes even though it's embarrassing, with Ayumu and Hinagiku following them thinking their date is real. Last, Hayate and Maria go to an aquarium, as Linn tries to get involve with the maid, but fails. Then they run into Ayumu and Hinagiku and they ask if they're really dating, and respond it's just their imagination. At sundown, Maria hopes she'll find a boyfriend like Hayate someday. The episode ends showing a phone ringing.

"May I kiss you?" All of the Cuties have had the same dream - one in which Hayate kisses them! Meanwhile, the indebted butler himself continues to unwittingly make all the girls' hearts skip a beat after having a troubling dream of his own! A tumult of love beginning from a single dream and someone's idea of a joke throws Hayate and the Cuties for a loop!

"I have to kiss someone, for Miss Nagi's sake!" As the time limit draws near, Hayate dashes through town looking for someone to kiss! And the Cuties, hoping to help Hayate somehow, are also running all over the place! The days of youth, and the first kiss - two things that everyone treasures.