Hayate no Gotoku! Episode 5, title name as Careless Gags and Kindness Bring Misfortune (不用意なボケと優しさが不幸を呼ぶ,Fuyōi na Boke to Yasashisa ga Fukō o Yobu?) aired on April 29th 2007, the English Animax dub aired on June 17th 2009.
Hayate wakes Nagi up and tries to get her ready to go to school, but she refuses and goes back to bed. Maria told Hayate that not only does Nagi not like to go to school, but she doesn't like to go outside since the time that Nagi was little and that she is the only daughter of the Sanzenin family. Just then, the phone rings and Maria picks it up and wants Nagi to call the person in the phone, but Nagi hangs up on that person. Afterwards, a mysterious girl angrily breaks in out of nowhere. Her name is Sakuya Aizawa, she is Nagi's relative and much like Nagi, she is a rich person. Sakuya was expecting to check out Hayate and wants him to be a comedian, but Nagi refuses that offer. Sakuya tested Hayate to bring up one of his funniest jokes, though she finds it not funny, but liked his style.
Maria suddenly ran out of tea while the visitor will come by. Maria wants Hayate to go buy a tea at the shop while he wears an expensive cashmere coat, and there will be consequences for Hayate if the coat is messed up. While Hayate is on the road to buy a tea without ruining a cashmere coat, he went to the park and met a girl named Isumi Saginomiya standing by the vending machines (right where he and Nagi first met). Hayate explains the she needed to put money in the vending machine, not a talisman/paper when she exclaims that the machine is broken. Since Isumi was lost and has nowhere to go, Hayate tries to help her (even though in his mind, he told himself to run to get out of misery), until a group of swordsmen surrounds them. Hayate takes Isumi away from the swordsmen and tries to escape, but Hayate and Isumi were about to fall into a lake. However, Hayate saves Isumi in the nick of time, though the cashmere coat got ruined.
Hayate became worried about what will happen to him if the coat is ruined. Isumi offers to pay for his coat since it got ruined because of her, but Hayate thanks her and explains that her thoughts for it are enough, and that it was his fault because he said he would protect her, surprising Isumi. After that, Hayate says that he'll protect her from "the evil men in black". While Isumi tries to explain Hayate about the swordsmen that they saw, she starts to dry his face and tells him to go home, otherwise he will catch a cold and then he'll die. As she says that, Hayate sneezes, making Isumi upset since she was too late. Hayate says that he's not dead yet and decides to take her somewhere safe. Soon after, Hayate takes Isumi to the Sanzenin mansion where she was suppose to be a visitor, then talks about Nagi, the master of the mansion, explaining how she's a little stubborn and selfish, but she's a very kind and cute girl. After ringing the doorbell for Isumi, he leaves her in front of the gate. Meanwhile, the swordsmen are trying to find Hayate, whom they think he kidnapped Isumi.
After dodging a bunch of falling squid, Ginta and Dorothy from the series MÄR can be seen among the crowd of people that were applauding for Hayate.
After Isumi had told Hayate that she was lost and asked him on what she should do, Hayate repeats this phrase to himself: "I must run away." This is a parody of when the character Shinji Ikari uses the phrase "I must not run away", from the series Neon Genesis Evangelion.
After Hayate had accidently told Isumi to "shut up", Hayate asks her what she thinks of the series "Ul***man". This is a reference to the series Ultraman.
Afterwards, Isumi tells him that her favorite character is Pestar.
As Isumi was trying to tell Hayate that the men in black where actually her butlers, the Japanese text for "oro" appears around her. This is a reference to the word Kenshin Himura uses when he is confused in the series Rurouni Kenshin.
During the preview for the next episode, Hayate uses the line "You will see the tears of time." This is a reference to the final line used in the episode previews of Mobile Suit Zeta Gundam.