Tsunade

Naruto was like the grandson that she had never had. He had snapped her out of a decade long funk in a matter of days, helped to save her life when her fear of blood nearly got her killed against Kabuto, and just brought a lot of energy to her life. She owned the kid, that was for sure. He was easily her favorite person in the entire village, bar maybe Shizune.

But for the life of her she couldn't figure out what the twelve year old saw in his crush Sakura. She berated him, slapped him, never listened to him, and actively spurred his advances in favor of chasing what would be likely be one of the most abusive relationships possible for her.

She wanted to try and make things better for him, maybe redirect him towards someone who might be more compatible with his personality and less violent towards him. So, to that end she called him into her office after sending all of her Anbu and Shizune home for the day.

Minutes later, an orange ball of energy exploded into her office.

"Hey Granny, I got your message! Do you have some sort of super awesome mission for me to do for you? Is there another princess or country that needs saving? The old pervert told me when I reach a half dozen he'd teach me another really cool new technique!"

"...The old man is ripping you off kid. You should be getting all the training you want for just saving ONE country. Jeez, maybe I should be the one training you instead of the lazy bastard. At least that way you wouldn't have to wait around for him to finish 'researching' for a whooping 15 minutes of training before he vanishes on you again. I know hands off teaching can be good for people, but he takes it to the ."

"You'd train me? I thought I didn't have the chakra control for any of your medical stuff or super strength."

"I'm a Sannin kid, I can do more than heal and punch. But we can talk about that later, I called you in to talk about your girl situation. I want to help you out."

"Really? You're going to help me get together with Sakura!?"

"...Eh, something like that." With a shrug, Tsunade yanked down the front of her shirt, showing her naked breasts to the young kid.

"Wha-? Hey Granny what the heck are you...doing..." Naruto's shout of surprise slowly trailed off as his eyes glazed over.

"Hypnotizing you with a genjutsu I put on my boobs to catch perverts when I get way too drunk." The Hokage answered conversationally. "Now then, I want you to tell me everything about why you feel the way you do about Sakura, and everything about your personality that you think might be relevant for dating."

"I love playing matchmaking."