Jann is minding his own business. He is playing by himself in the courtyard with a wooden sword: this definitely constitutes minding his own business. Nothing that follows is his fault.
"I don't know. Cath thinks I should just ask you to go find an excuse to bring up marrying me as a possible solution to the crown, without bringing my hopeless crush into it at all. I'm waffling."
"That was my plan originally anyway. Perfect plausible deniability. 'Hey, Reko, know what I bet would fix the crown'."
"Reko's pretty good at drawing people out, are you sure you could actually leave my hopeless crush completely aside?"
"I had a little trouble coming up with a plausible reason for you to ride all the way into Ferdinandia just to casually bring up marrying me if I hadn't sent you to do just that."
"You visit him sometimes," shrugs Jann, "I escort you because that's my job, you aren't in the same room as us all the time, ta-da."
"It's possible I'm overestimating his probable suspicion just because the ulterior motive is so obvious to me."
"According to my girlfriend," (this title is currently held by the sister of a knight school friend), "the twin princesses of the Enchanted Forest are both married to the same woman, which I think I'd heard before, and they have kids, which I hadn't, fancy that, Reko, hey, you know what occurs to me."
Jann waits for a moment when Milo happens to be out of a room that he and Reko both are in.
Such a moment occurs when they finish a game of chess and Milo goes to see where Cath has wandered off to.
(Jann is familiar with the concept of not wandering directly into sensitive topics! Really!)
"I've heard her say his name," he says. "Well, meow it. But very recognizably. Now that was amazing. Milo having a conversation in which he provides most of the words isn't anything new."
Pause to gauge response...
"You know what would probably fix the crown?"
"I mean, the thing the Enchanted Forest princesses did would probably have to work, etcetera, but I bet if you married Milo that would fix it."
Jann giggles like he's made a stupid joke as opposed to proposed something that at least one person is very serious about.
"The princesses of the Enchanted Forest have a few things Milo and I don't, Jann," he points out. "Even if it did fix the crown, it would only put the problem off for another generation, and then you or your heirs would be left to deal with the crown's opinions of nontraditional princes."
Jann shrugs. He is playing "this was a random idea, not important"; nitpicking about how they could actually look into that question would not fit. "Please don't make me inherit Raxwell. I wouldn't like it at all."
"I'm not planning to make you inherit Raxwell. Have you brought up this suggestion of yours with Milo?"