The chapter begins with Seishiro being attacked by an mysterious assailant as she is leaving school who calls her 'Black Tiger'. Raku tries to intervene in their fight, but get a kick to the face instead.
He is taken to Seishiro's flat with the mysterious assailant accompanying the 2 and Seishiro introduces her to Raku as Paula McCoy, a fellow Beehive assassin that worked with her in America and is known as 'White Fang'. Paula has constantly compared herself to Seishiro, determined to beat her in something since Seishiro mistook her for a guy because of her flat chest. She is now disgusted at how passive Seishiro has become, which demonstrated by her making beef stew for both Paula and Raku, for which Raku compliments her for and that embarrasses her. Paula sees this and decides to challenge Seishiro to duel and if Seishiro wins, then Paula will stop bothering her, but if Paula wins,then the Black Tiger must prowl the streets of the US once more. Seishiro accepts the challenge, so Paula then reveals the challenge to be that the winner is the first one to steal a kiss from Raku's lips within one hour.

Raku isn't best pleased with the competition and neither is Seishiro, as she wishes to not kiss her mistress's boyfriend. Paula isn't too bothered by this and reminds Seishiro of the Beehive's iron rule: 'Never back down from a challenge you've accepted'. Seishiro withdraws her objection and the duel begins with Paula making an early move on Raku's lips before Seishiro fires a few shots from her gun to separate the 2. Seishiro continues to open fire on Paula, who dodges them by hiding behind Raku, who is and will remain unharmed (physically) throughout this chapter. Raku then bolts out of Seishiro's flat, with the 2 assassins chasing him down. Paula is the first to grab his attention, but Seishiro is quicker and corners Raku off and makes an attempt to kiss him before slapping him away, due to her embarrassment. Paula takes advantage of this by capturing Raku and covers her tracks by way of a smoke grenade.
Paula takes Raku to an abandoned warehouse and ties him up to a concrete pillar, where he tries to convince her to not kiss him, but it falls on deaf ears. He does however, works out that she wants to win Seishiro's respect rather than the duel she challenged her to. Meanwhile, Seishiro is agonising over probably losing the competition that she is motivated into a demon-like state and almost immediately finds Paula and Raku. She breezes past Paula and smashes the pillar Raku is tied to, before putting 2 fingers on his lips and before touching her lips with those fingers, which counts as stealing a kiss and Paula agrees (out of fear).

The rankings from the recent exams are up and everyone has passed and scored within the top 50% of the year - everyone except Marika who scored 185th. Everyone is more concerned about this than she is, as she believes her time is better spent studying on how to be the perfect wife rather than academics. She then realises that a study session with Raku is beneficial for her in regards to her academic and romantic life and he agrees when finds out that her next exam is tomorrow. Raku arrives at Marika's with Chitoge in tow because a: she doesn't trust Marika and b: ranked 5th so is pretty smart herself. They begin studying with Marika making progress by applying her twisted logic to Raku's teachings. Whilst doing his own studying, Raku encounters a problem that he doesn't understand and Chitoge helps him, which irritates Marika, so she decides to interfere. Chitoge questions her commitment to passing to which Marika says she's not that smart and Raku asks how she passed the school's entrance exam to which she responds that money helped. She reveals that she's joking and she did pass after an all-night revision session, which means she is smart enough, just not motivated enough to make use of it. They end up studying long into night and in end they fall asleep. Raku wakes up during early hours of the morning and goes to get blankets for all where he overhears Marika talking in her sleep professing love to Raku as well as a lot more. She takes the exam the next day and scores 38, with 40 needed to pass. The prospect of taking a make-up exam doesn’t bother her, but Raku noticed that she changed her answer from a correct to a wrong one, meaning that she would've passed if it was correct.

The chapter begins with 2 bonus comics based around the cover illustration for this chapter.
Chitoge is complaining that her lips are chapped and so one of her friends gives her some lip gloss to cure it. She then remarks how beautiful Chitoge looks with it and suggests that Raku will think the same if he sees her wearing it. The next morning Chitoge wears some lip gloss and tries to get Raku to notice, only to fail. She tries again the day after, but with expensive shampoo instead. Unfortunately, Raku is just as clueless today as he was yesterday, so Chitoge goes for something more obvious, nail polish, and Raku doesn't notice that either. As a desperate final move, Chitoge changes her ribbon only for him not to notice, but notice that she has changed the meat in her lunch. After school Chitoge bites the bullet and asks Raku directly if he noticed anything different. He initially guesses wrong before eventually correctly guessing the lip gloss she started wearing as well as the shampoo and nail polish, with his reasoning for not mentioning it earlier being that guys don't need to mention it when they think girls look good. Chitoge corrects him all whilst both are embarrassed by the whole exchange.

Ruri has lost her glasses as she left them on a windowsill of an open window whilst she went to get a cloth to clean them. Upon hearing this, Raku and Kosaki volunteer to help along with Shu, but she declines Shu’s help as she doesn't want to owe him and swiftly karate chops him after he inevitably makes an unwanted comment about Ruri – his current shtick. They leave the classroom, but Ruri walks into the door, then trips over the doorway and mistakes someone else as Raku, because she is that blind - not blind enough to accurately hit Shu when he annoys her. They start looking in the garden area outside the window where Ruri had left her glasses, but the search ends up fruitless. Ruri then suggests a dark and secluded place as where the glasses could be and admits to Raku that it is a good place to fool around in. This embarrasses Kosaki (I wonder why), so she heads to the teacher's office to check if the glasses have been handed in yet, leaving Raku and Ruri alone. Raku breaks the silence by asking Ruri if Kosaki is in love with anyone and seeing this as an opportunity to trigger some progress between the 2, she begins to admit Kosaki has a crush and it is him, only for Shu to interrupt her at the last second. Kosaki returns empty handed, so she and Raku decide to check up in the hallway where the glasses were last seen, leaving Shu and Ruri to argue whether or not it is okay to help those 2 realise that they love each other. The argument is interrupted when Raku and Kosaki appear with Ruri's glasses.
The next day Ruri tells Raku that she was joking about Kosaki having a crush and that is great relief to him, before admitting Shu might be right.

It is almost Christmas and the gang are planning to have a party, but Chitoge can't come and besides Christmas makes her nervous. On the way home, Chitoge explains her nervousness comes from the fact that her mother is coming home for Christmas and she spends it with her family. However, Chitoge’s mother spends all her time running a multi-national business conglomerate, so much that this only time she gets to see her. Chitoge is then interrupted by a text from her father saying that her mother is coming home tomorrow and he wants to introduce Raku to her.
Raku arrives at Chitoge's house and everyone is rushing around getting the place ready for Madam Flower (Chitoge's mother as her first name Hana which means flower in Japanese) arrival. When Hana arrives, she quickly embraces Adelt (Chitoge's father) before asking him if he did the task she set 2 months ago. He hasn't, so she quickly orders that he completes this by Christmas and if not, his eyeballs get plucked. She then moves onto greeting Chitoge and asks how old she is and how she's doing at school, so Chitoge responds with her recent exam rankings which doesn't seem to impress Hana. Chitoge then introduces Raku to her mother, who intimidates him by telling him the consequences of hurting her daughter would far surpass his imagination. Hana then spots her daughter is still wearing a ribbon she gave her a long time ago and asks if she wants a new, better-looking ribbon to which Chitoge, defeated, agrees. A member of her entourage informs her that her secretary has collapsed from exhaustion and all of her backups are all unavailable, so she enlists the services of Raku to see what kind of man is her daughter's boyfriend and if he does well, there's a penthouse suite room at a deluxe hotel at Christmas Eve with Raku and Chitoge’s name on it.

Now that Hana has a new secretary, she wastes no time putting Raku to work by getting him to commit memory in 5 minutes some documents, the day's agenda and her secretary's manual. Raku continues this task in Hana's Limousine in which she's conducting a teleconference using 5 different languages while they are on the way to Company XX to advise their CEO on how deal with their budgetary deficit. When they get there, the CEO is grovelling at Hana's feet, asking to be stepped on as punishment for his failures, which she declines but still does it anyway. Hana then tasks Raku to buy her a coke, whilst he is doing that, she calls him and gets him to buy some really expensive and Japanese exclusive gifts for friends and business partners for which he'll need to zig-zag across Tokyo to get - Luckily, he has 3 hours and her credit card. He returns with everything Hana asked for, but is 30 seconds late and so she is as well and that will not do. Her next meeting is with AB Corporation, which is just across the street from Hana's office, so she zip-lines in to save time.
Raku gets a break and calls Chitoge to see if she is alright because she seemed upset after Hana didn't seem too thrilled about her still wearing the ribbon that she gave her and Hana's generally cold attitude towards Chitoge has got Chitoge depressed. Raku is convinced that Hana loves Chitoge and suggests to her that she asks her mother to spend Christmas Eve together. However, when Chitoge does this, Hana declines the offer as she has planned to work that day and when Raku finds out what she has done, he exasperatedly asks why and her response is that there is only work that she can do, so she must do it to make the best use of her gifts.

The chapter begins with Raku hustling through documents at a breakneck pace, which impresses Hana enough to up his compensation (his pay for working as her secretary) and books the hotel room she mentioned at the end of Chapter 59. However, Raku doesn't want any money nor the hotel room, as he instead wants Hana to spend some free time (that he'll create by working extra hard) with Chitoge, to which she gives a non-committal yes as an answer and that is enough for him. Raku powers ahead and completes all the stuff she needs for next month and now Hana has free time that she can spend with her daughter, although Hana declines his offer and refuses to accept the present, he bought for her to give to Chitoge, because there is now more time for some more work. Incensed at Hana's response, Raku begins to tell her off only to be interrupted by Hana pulling out a present she was going to give her, but can’t now as she'll miss her chance. Raku is confused he thought she didn't care for Chitoge only for Hana to correct him, explaining that she talks like she does to Chitoge because she gets nervous around her, but has been too hard on her as she is very proud of her daughter. She now believes that Chitoge doesn't like her any more (hence getting her some alone time with her boyfriend), so Raku then corrects her by explaining how Chitoge really feels about her mother and orders Hana to spend time her daughter, only problem is that she is leaving for the US in 3 hours, so Raku sends her to the hotel room she booked, while he dashes off to get Chitoge. Meanwhile, Hana receives a message recommending to board her flight earlier to avoid an incoming snowstorm that will ground the aeroplane if it leaves at its scheduled time.

Raku is informed by his limo driver that they're going nowhere due to traffic that has piled up because of the ever-increasing snow. Raku then borrows a nearby bike and rides off with Chitoge to the hotel, whilst explaining the entire situation to her. When they arrive at the hotel, they find out that Hana has left for the airport and then immediately chase her down, but arrive just as the plane takes off. Raku calls Hana to get her come back, only to be told that she is thankful for telling her how Chitoge feels. Raku calls out her cowardice and hands the phone to Chitoge to help convince Hana to come back. The plane Hana was on turns around and lands back at the runway, nearly running Raku and Chitoge over. Hana exits the plane before having a heart to heart with Chitoge, in which they patch things up, before Raku hands Hana the keys to the hotel room and promises to limit the damage that occurs from Hana missing the meeting she was going to attend. Whilst in the hotel room, Hana gives Chitoge her Christmas present and reveals that Raku is the reason why she wears her current ribbon. Hana lets her daughter go and be with her boyfriend, who she finds in Hana's office sleeping and thanks him for what he has done.
There is a bonus comic set after Chapter 57, where Seishiro demonstrates her make-up skills on Chitoge.