Jirou:
He raises an eyebrow. Ah. Poison. He should've known. Suddenly he didn't have as many problems about keeping Kimiko's goals secret from him anymore, or the Masuku he chose for his plan. Funny how a respected leader poisoning him for questionable reasons and potentially killing him a few months down the line could provide such astonishing clarity.
"I see."
he says with a straight face, as if nonplussed.
"Very well, I shall do my best. when do we start?"
Despite being a complete nerd with no actual experience in love. One of the basic skills of being a shinobi is being able to imitate lives you never lived or experienced. Honestly, if he can't talk his way through this, he is in trouble as a shinobi in general.

Letter Delivery Mission:
"Uhh-aaaaH! No just...." Kazuo says looking away from Usagi
"Thieves and thugs" Miho pipes up "he somehow is always is there in the nick of time to foil them out of nowhere."
"Its nothing heheheh..." he says scratching the back of his head
"But you always somehow show up just in time! How do you do it?"
"Oh y'know.....trade secret....huh this package is for your family, Miho..."
Kazuo had no idea how kept running into such situations, it was all his bad luck, he thought to himself.
"And this similar package is for the Ishikawa family..."
Meanwhile Kimiko and Naneko were rifling through the letters
"So....uh....how you doing?"
"...."
"Not much of a talker?"
"...."
"Well then I guess you like listening mo-"
"Shut up. To be silent, is to be shinobi."
Naneko's voice is a curt half-whisper. Kimiko furrows her eyebrows and just glares at her. Rude! Then goes back to sorting the letters only to find a certain letter: It has a heart stamp seal on it used in love letters and its address reads:

From: Jirou Ishikawa
To: Kikenna Masuku

The two Genin stare at it uncomprehending for a few moments. Jirou and.....Kikenna? The rebel Masuku? Naneko's older sister? Why? She was a known seductress- a fierce outspoken one, with specialties in poison and fire jutsu. You probably couldn't find two people more different if you tried.
"....Who does your brother think he is, going after my sister?"
Naneko says with a tinge of emotion, glaring accusingly at Kimiko
"I don't know, maybe your sister put the seductive wiles on him! He was never interested in that kind of thing before!"
Kimiko looking suspiciously at Naneko.
"As if my sister would ever be interested in someone like him. He's clearly pathetic for even trying."
"Hah! As if my brother would have such low standards to fall for some like her!"
"You have it the wrong way around, Jirou would be too easy for her bring him under her sway."
"As if my brother would be seduced by your sister!"
"As if my sister would ever accept his advances!"
Suddenly Yuyuyu and Miho comes between them before this can escalate.
"Girls girls, none of this is our business!"
"Our job....is to deliver the letter. Not to fight over it, okay? Relax." Miho says
They both glare at the reasonable ones breaking them up then grunt and get back to sorting the mail.