In general on character relations: I'll have a more full character background ready shortly, which ought to help you guys make suggestions on how we fit together.
randomling: Daffyd doesn't have any children, so he's unlikely to have spent much time around Catrin. As her family is well-to-do, there might have been a day or two spent posing for a portrait, but that's only enough for her to have ideas about what he's like. (If you like that, then have a think about when the portrait or portraits were painted - that will make a big difference to the impressions made.)
It does occur to me that the "old soldier" in your character's background could be "cousin Willem" from mine; if that works, then they still won't know each other well, but there's an obvious tie-in. (And we save on NPCs!

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SolosAddie: Maybe Kardus' grandfather and Daffyd's mentor were adventuring companions? I certainly intended that my character was taught magic by a wizard-adventurer, so that seems like a reasonable tie. I'm guessing that Kardus' mother has been one of the other people to bother... I mean, "visit" Daffyd since his wife died, so there's that as well.
Unkabear: Heh. We've ended up with very similar backgrounds - especially because I thought that Daffyd was an almost-adventurer. Maybe the two intended to adventure together when they were boys? Dalen would have gotten married when Daffyd was just fifteen, so life started getting in the way pretty early-on.
Hmm. Assuming you're with me so far, I think Daffyd would have taken his would-be companion's decision very badly - called him a coward, refused to go to the wedding, stormed off into the world to find a tutor without any further words. When the hedge wizard returned to the valley with a wife and the intention to settle down, I think he'd be too proud to look Dalen up and apologise.
That leaves us with their parallel bereavement as a good reason to refound their friendship. It seems like Dalen is sensible enough to see this (while Daffyd isn't), but you really ought to fill me in on your thoughts before I go any further.
