Kakashi sat quietly, his chin resting in his hand as he thought for several seconds. To be honest, even as Hokage, matters of love were something he could never quite grasp. Power and duty he understood well — but emotions? That was an entirely different battlefield.
Naruto watched him with a knowing grin. "Kakashi-sensei, don't think too hard about it! Just take my advice — you're not getting any younger. You can't spend the rest of your life as a bachelor! Find someone, live your life, and be happy. That's what a grown man should do!"
Kakashi frowned slightly, rubbing the back of his neck. "Naruto, it's not that simple. I've never really thought about these things. I've always been… unfamiliar with love."
Naruto sighed deeply, his expression softening.
In his previous life, both Kakashi and Guy had remained single until the end — two lifelong bachelors who gave everything for the village. When the Ōtsutsuki clan invaded and destroyed Konoha, both men had fallen in battle, side by side. Neither of them ever got to experience the peace or companionship they truly deserved.
That memory always stayed with Naruto — one of the small regrets that never faded.
Now, in this new timeline, things were different. With Tsunade herself trying to play matchmaker, Naruto didn't want to let the opportunity slip away. If there was even a small chance that Kakashi could find happiness with Shizune, then he wanted to push him toward it.
Naruto leaned forward, a teasing smile tugging at his lips. "Listen, Kakashi-sensei, just give it a try. Don't overthink it. Who knows? Maybe Sister Shizune's the person who'll finally make you put down your books and open your heart."
Kakashi glanced up at Naruto, mildly amused but thoughtful. "You really think so?"
Naruto nodded firmly. "I know so."
And with that, the two men spent a long time talking — about love, regret, and the possibilities of starting something new.
Meanwhile, at Tsunade's house, the evening had quieted down.
After Naruto left, Tsunade exchanged a look with Jiraiya — the kind of silent understanding only old companions shared. With a small nod from her, Jiraiya stood and motioned for Sai to follow him downstairs to his personal study — a cozy room with a terrace overlooking the village lights.
Once inside, Jiraiya shut the door and turned to Sai. "Perfect timing. Let's discuss the direction for the second book of Icha Icha Heaven."
Sai blinked in confusion. "Jiraiya-sama, at this hour? You want to talk about that now?"
Jiraiya shrugged helplessly. "What else am I going to do? Might as well make the most of my time!"
Sai tilted his head, thinking. "I suppose that's true."
Jiraiya smirked as he pulled out parchment and a pen. Sai, however, seemed distracted. "Do you think Tsunade-sama sent us away because she wanted to talk to the others about something?"
Jiraiya chuckled and handed Sai a chair. "Definitely. Why else would she glare at me like that? Whatever she's planning, I'd rather not be in the crossfire. Now sit — let's brainstorm."
Sai nodded obediently, realizing the wisdom in that. Before long, the two were deep in discussion about the second volume of Icha Icha Paradise.
The first book had been a massive success — enough that the publisher was already begging Jiraiya for a sequel. Readers across the shinobi nations were flooding them with letters, demanding the next installment.
So, with nothing urgent on his schedule and a fresh burst of creative energy, Jiraiya decided to start drafting ideas, with Sai offering suggestions and sketches.
Upstairs, Tsunade, Shizune, Ino, and Sakura sat together around a low table. Sakura had just brewed a pot of tea, filling the room with a gentle aroma.
She poured for everyone, setting small plates beside their cups, then finally served herself.
They lifted their teacups, blew softly on the steam, and took a sip.
After a quiet moment, Shizune set her cup down. "Tsunade-sama, I… I still need to think about this. I'm not sure."
Tsunade sighed and leaned back in her chair. "Alright, take your time. But Shizune, I really want you to think about it seriously. You've spent your whole life taking care of others — it's time you let someone take care of you. You can't always be alone."
Ino nodded enthusiastically. "She's right, Sister Shizune. Kakashi-sensei is a great man — he's smart, reliable, and now he's even Hokage again. And, from what I've seen, he's never had a girlfriend. You two might actually be a good match."
Sakura smiled knowingly. "Yeah, I agree. Ever since Kakashi-sensei took over as Hokage, I've never once seen him with a woman. But I do know he reads Jiraiya-sama's Icha Icha books all the time."
Tsunade snorted, crossing her arms. "Hmph. Typical. Those kinds of men — the ones who act aloof and pervy — always have a hidden passionate side. Trust me, Shizune, deep down Kakashi's the type who craves connection. Once you get past his mask — literally and figuratively — you'll see how much he can care."
Shizune stared into her tea, her thoughts swirling.
She had been with Tsunade since her youth — more than an assistant, almost like a daughter. Though Sakura was Tsunade's official student, Shizune had been her very first apprentice.
Watching Tsunade and Jiraiya finally find happiness together made her heart ache with envy.
Still, she couldn't help but hesitate.
Once, after a few too many drinks, Shizune had joked, "I envy Tsunade-sama's figure… mine's as flat as a board."
Now, faced with the idea of being paired with Kakashi — the calm, composed, and legendary Copy Ninja — her insecurities surfaced again.
Kakashi is kind. He's upright. He's the Hokage.
But… what could he possibly see in me?
Her confidence faltered. She wanted to believe in love, but the fear of rejection was stronger.
And ever since Tsunade had mentioned the possibility of them getting closer, things between her and Kakashi had grown awkward. They avoided eye contact, and Kakashi had even stopped delegating paperwork to her directly — a silent retreat that Shizune took as rejection.
She had even considered resigning as his assistant, thinking it might ease the discomfort between them.
Tonight, she had come to talk to Tsunade about that very decision — but Tsunade wasn't letting her give up so easily.
"Shizune," Tsunade said gently, "I know you're afraid, but you need to be brave. You don't dislike him, right? Then what's stopping you? They say when a woman chases a man, there's only a thin veil between them. Break through it."
Tsunade's grin turned teasing. "Men like Kakashi — quiet, guarded types — they need someone bold enough to reach out first. Once you do, they open up completely."
Shizune blinked in surprise. "You… really think so?"
Sakura leaned in with a smile. "Tsunade-sama's right. Kakashi-sensei might be brilliant, but he's dense when it comes to emotions. He's practically an introvert! You should reach out — who knows? You might be surprised."
Ino giggled. "Exactly! I didn't think I'd ever fall for Sai either, but after reading his emotions with my Mind Body Switch Technique, I realized how deep his feelings ran. Once I saw that, I knew he was worth it — and I chose to love him."
Hearing everyone's encouragement, Shizune hesitated… then finally smiled faintly. "Alright. Maybe… maybe I'll give it a try."
Tsunade smirked triumphantly. "That's my girl."
Back in the Hokage's Office, Naruto and Kakashi wrapped up their conversation.
Kakashi exhaled, finally breaking the silence. "Alright, Naruto. I'll give it a try. If things are really as you say, I'll… open my heart to it."
Naruto grinned wide. "That's the spirit, Kakashi-sensei. Sometimes, you just need to take the leap."
Kakashi nodded slowly, determination glinting faintly in his single visible eye.
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