Answer diplomatically

You, answer her diplomatically? Pft. The sun will rise before that happens. But this is where you use your limited experience as an cheap labor editor for your master's Icha-icha series to answer her. Despite the tacky perverted scenes, you realise that the stories are quite well written, not that you're going to confess that to Jiraiya even under threat of ****. One recurring theme that you notice in those books are that you should always try to be honest at all time. However, being honest doesn't mean you don't mince your words. Instead, you try to tell the truth in the best manner possible.

"Shizune, I think you're amazing... uh... and pretty... And pretty amazing."

It seems that you need more practice in being more honest diplomatically.

"Really?" Shizune asks, realizing that you're having problem articulating your thoughts and thus prompting you to say more.

"Just now, when we're at the office, I'm thinking that once I become Hokage, it would be nice to have someone very dependable as assistant and I ended up picturing me sitting at the desk with you helping me."

"You're just flattering me."

"No, I'm not, I swear it's true, Hokage's honor. Future Hokage's honor."

Shizune smiled wistfully. "I'm thankful for the vote of confidence, I guess. But I'm not as pretty as you said Naruto."

"Sure you are."

"That doesn't explain why no one approaches me for a date until now."

"Eh, that's easy. Everyone's afraid of Tsunade. Heck, even I'm afraid to ask you for a normal lunch between friends as I like my head and whole body to remain unharmed as much as possible. Sure, she can heal everything right up after clobbering me to the ground, but the pain, the phantom pain still remains, you know."

She giggles at your comment. "But I'm much older than you, Naruto."

"Despite that, and despite you're like an older sister to me, I still stand by my statement that you're pretty, Shizune." You then recall that a weeks prior, you experienced a lucky pervert or as they say it, 'lucky sukebei' event. After finishing a mission, you went to the local bath to enjoy a dip in the hot spring. It was there, you accidentally come across a hole on a wall and despite your initial ****, you ended up peeking through it. You were rewarded by a sight of Shizune in her full naked glory as she bathed in the woman's section. That gave you plenty of materials to work on later that night. And another, up to last night. "Yeah, you have a pretty amazing body," you mutters as your drools drip on the ground.

"Wait? What!" Shizune questions.

You're saved from answering her as the two of you finally arrive at the hospital.