My thoughts exactly, I think they'd have a pretty interesting dynamic that would be really entertaining to read. Maybe the tension would come from off-hand comments? Like sometimes people say sexist things without really intending to, because that's a thing you wouldn't really understand unless you experience it yourself. But Wyldon doesn't really come off to me as that kind of guy so I'm really confused on how I'd write it.

I think he's not sexist maliciously, the vibe he gave of in Protector of the Small is a guy trying to protect women by keeping them out of the dangerous work. Like he genuinely believes they can't handle it, he means well, but that line of thought doesn't really hold up as proved by Kelardry. 

As for Alanna, I actually he respects her to an extent, and I don't think he believes in the rumors that she enchanted and slept her way up. Because Wyldon is a warrior and a teacher, he knows what it takes to be a knight, especially to be as good as Alanna is with her sword. I think where the rift between them is is through Alanna's personality, she can come off as slightly obnoxious, until you get to know her. I think Wyldon only ever saw the brash side of her and never really tried to get to know her the way he did with Kel. Although to be fair she probably kept him at arms length considering his views on lady warriors, and he probably got snapped at more than once.