Connie
"I think you'll like Ma. Hard-working woman who doesn't take anything from anyone. But as long as you respect her and her family and her farm, a total sweetheart. The kind that'll invite you in for dinner and a night's rest."

He spoke very fondly of his mother, if it wasn't obvious before than the fact that they had a good, healthy relationship should be clear now. 

"Alright... You're gonna wanna take a right here..." He'd start, looking around at the natural landmarks and starting to help Damien find his family farm, Ashroot Farm
Argelia
He has the horses turn to the right, "My parents are fine, I suppose. They're both retired back in Camlorn, While on my little adventures I have to wrangle any and all logistical issues with the mining business. I doubt my father would be happy with the changes I made to that," He says with a chuckle, "But it's not like he can do anything about it."
Connie
"Mining business? I heard that there's good money in the mines if you can handle the work. Though I don't know if I could ever do that." He'd absently chuckle and shake his head, gesturing to a left up the road. 

"Turn here, then just keep straight. Should see it coming up"
Argelia
"I work logistics." He says, "Mine placement, mostly, as well as some of the managing." The horse take the turn, "Most of the managing I leave to the locals, though, since the mines are all the way in Elsweyr. I only take some of the profits, most of it goes back to the communities."