*looks at wall of text* Seems you may have gone a bit overboard here, @1234qwerty. Dunno if I'll have the time to read through the whole thing, but I gotta comment on this...
Now, I realize that Keiko x Shikamaru is a desirable ship for a lot of people, and I'm kind of a fan of the idea myself, but... this seems like a bad idea all around.
1. Keiko has not even decided whether or not she wants to marry a Nara at all. Trying to set her up with Shikamaru given that seems like it ignores her agency in the matter when Hazou has already stated he'll support her decision. Let's not be a hyopcrite.
2. Shikamaru is not our friend. Not yet, anyways. He was one of our minders when we were in Leaf and Hazou got along well with him, so there's a potential for friendship there, but we aren't there yet. Trying to get him to not only tell us his father's intentions in an important meeting that is about to occur and also trying to hook him up with Keiko while we're at it isn't really something that we should be doing as just friendly acquaintances, even if we're likely to be allies soon. And for all we know Shikamaru is interested in someone else, or has an existing arranged marriage in the works.
1. Talk to Shikamaru
a. See if he's willing to lean on his father for a marriage with Keiko.
1. Invite Shikamaru to our residence before speaking with his father.
a. Clear this with the team/Jiraiya beforehand, including what we expect to bring up in the discussion.
b. Small talk about the book he recommended to us and what's happened in Leaf since we've been gone to make him comfortable. - If he's aware of his father's clan offer to Keiko, do this after the main discussion.c. Bring up the offer his father made to Keiko- Use Clear Communication.
- What does he think his father's motivations are?
- Without being sure, we(more importantly) don't know which offer we prefer.
- We don't know what Shikamaru's relationship with his father is like, but we like Shikamaru and we hope it wouldn't be rude to offer him the opportunity for some political capital. It occurs to us, if he insisted to his father that should Keiko marry into the clan, he wishes to be her husband, he could leverage a refusal into furthering some other goal or if his father acquiesces *insert-benefits-of-marrying-Keiko-here*. Stuff along the lines of Keiko being low maintenance(or let Keiko make her own case) and marriage being an inevitability otherwise.
Now, I realize that Keiko x Shikamaru is a desirable ship for a lot of people, and I'm kind of a fan of the idea myself, but... this seems like a bad idea all around.
1. Keiko has not even decided whether or not she wants to marry a Nara at all. Trying to set her up with Shikamaru given that seems like it ignores her agency in the matter when Hazou has already stated he'll support her decision. Let's not be a hyopcrite.
2. Shikamaru is not our friend. Not yet, anyways. He was one of our minders when we were in Leaf and Hazou got along well with him, so there's a potential for friendship there, but we aren't there yet. Trying to get him to not only tell us his father's intentions in an important meeting that is about to occur and also trying to hook him up with Keiko while we're at it isn't really something that we should be doing as just friendly acquaintances, even if we're likely to be allies soon. And for all we know Shikamaru is interested in someone else, or has an existing arranged marriage in the works.