[X] I Can Tell That We Are Gonna Be Friends
"What am I, five?" Konohamaru (what is the deal with ninja parents? Why is Ami your only friend without a 'significant' name?) scoffs. "I'm not tellin' you anything for a lousy chocolate bar. How do I know you aren't spies for a foreign village?"
You're actually kind of impressed. "Huh. You're smarter than I gave you credit for."
"Of course!" He puffs out his tiny chest. "I have to be smart if I'm gonna be Hokage one day."
"Ehh? Quite the goal you've got there," you remark. "You sure you're up to handling all that diplomacy stuff? It's a lot of work. They'll make you talk to total jerks all the time, and you won't be allowed to hit 'em."
"I definitely can do it!" His nod makes his ridiculous hat-and-hair combo wobble, and a strange gleam comes into his eyes. "If I have to do it to be Hokage, then that's what I'll do. No shortcuts, just like the Boss said."
What sort of appalling things have they been teaching this kid? Shortcuts are the father of innovation!
In any case, you've got traction now; time for the all-out rush.
"Well, y'know," you say slyly, "one thing you need to be Hokage is the approval of most of the clan-heads. And as the future leader of the Yamanaka Clan, I can't say I'd approve of a Hokage who wouldn't help a lady in need."
Konohamaru snorts. "What lady?"
"Ami," you say without missing a beat, gesturing at her.
She looks surprised, but inclines her head politely at the kid. By civilian standards she isn't dressed femininely, but between her tunic-and-leggings combo and her long braid, all it takes is her height and her slight embarrassment at being bluntly called a lady to make her look the part of a kindly kunoichi onee-san.
"Your uncle called her names and made her sad," you elaborate. "Kiba and I are trying to get him back to avenge her honour." You pinch Kiba before he has a chance to so much as snicker.
"Tch. What do I care what he says to some girl?" Konohamaru mumbles.
"Isn't a Hokage supposed to care about everyone in the village?" you ask archly, and you're pleased to see him flinch.
Eventually the little sourpuss caves. It isn't him trying to steal Asuma's smokes, so he doesn't know anything about any traps, and he can't think of anyone else who'd bother. He does know that his uncle eats lunch at the Yakiniku Q every day and always orders the sausage platter. In addition to this helpful pranking info, over which Kiba and Ami are pleased as punch, you learn that Asuma and Konohamaru's dad don't get along so well, and that his mom says it's because Asuma left Konoha for a long time.
Ami gasps. "He was a missing-nin?"
"No!" Konohamaru scowls. "It wasn't like that, he had permission or something; Grandpa let him go. But Dad was mad anyway." He shrugs, as if to say, 'Adults. What the hell, am I right?'
"Well, now that we know what your dad thinks, what do you think of 'im?" you ask. Kids sometimes notice stuff that older people don't, after all.
Konohamaru looks somewhat taken aback. "Um... I don't know..."
You tsk. "Are ya a ninja or not? You gotta have some kind of opinion." You hope he spits it out quickly; someone kind of pissed off is headed your way, albeit much too slowly to be looking for you.
"... he's nice," the kid says finally. He looks at Ami. "I don't know what he said to you, but he probably didn't mean it. Sometimes he just says stuff."
Ami frowns, but nods.
"There you are!"
A black-clad figure pounces on the kid.
[X] Help the kid out. It's only fair after he told you what you needed to know.
-> [X] Paradise-Viewing. Not going to do much against the guy long-term, if his general level of strength is as solid as it feels, but it should make him let go of the kid for a second, and a second's all you need.
-> [X] Kawarimi with Konohamaru and then slip out of the guy's grip.
-> [X] Write-In?
[X] Ask the kid to introduce you to his playmate. You're amazed he hasn't seen fit to do so already; clan children nowadays! Why, back in your day...
[X] Tough break, kid. See ya 'round.