Connie
The wilds of Eastmarch, with its trees tall, it's air fridged, and it's hostiles many, could be seen as an unforgiving place, though several of the wilds in Skyrim are

But to Darthan, they were also home. 

With the sound of his leather boots crunching on the snow covered ground mixing with the ambience of nature around him, the Blond haired Dunmer felt almost at peace, closing his eyes for a moment and taking a deep breath, exhaling with a smile

"This is really happening" He'd say to himself, his voice full of awe and excitement. His hand going up to the necklace that his mother gave him. Indeed it was, after all these years of hardship, his dream was finally coming true. 

Exploring the world, delving into ancient tombs, fending off fierce beasts, it all made the smile on his face grow, the young lad drawing his blade and thrusting it outward dramatically, before returning the arm to his side and giving the sword a small spin. Returning it to his sheathe

He was gonna make his Ma so proud... Now he just needed to find a place to start.
Argelia
Horse beats, two horses trotting along the road, pulling a fancy looking carriage. A man sits on the seat holding the reins, he's wearing very fancy clothes, his cloak pulled tight and a scarf covering most of his face. The glint of a mask tied to his hip would draw the eye of most.
Connie
Hearing the sound of horses, he'd step along to the side of the road as to stay out if the way. But then he noticed just now expensive the carriage looked, how well tended the horses looked, and most if all the glint on his side that didn't come from a weapon... His curiosity was struck

He'd give the man a small wave, his stature friendly, hands away from his weapon, speaking up when he was close enough 

"Hail, don't think I've seen you around here before." His voice was more of a young curiosity than anything else
Argelia
"Whoa!!" He calls out the horses, slowing the carriage. Further observation would show that he wasn't unarmed, on his left hip was a sheathed rapier, more extravagant than the mask at his right. "I've only recently arrived in Skyrim. My job led me here. I'm a cartographer by trade, it leads me to all sorts of places."
Connie
"Only just arrived?" How exciting! So his hunch of the stranger not being from the Eastmarch area was indeed correct in a way

"Do you maybe need some assistance getting around or something? Or maybe just directions to some of the close by villages?"

It was a genuine offer, after all he's lived in Eastmarch all his life, it's only polite that he help a newcomer out if wanted.

And a Cartographer... Maps and such if Darthan recalled correctly?

"Where all have you been? Where do you come from? How do you like Skyrim so far- Sorry for all the questions"

He might be smothering the man, and for all he knew Darthan was holding this man up on important business. So he did his best to quiet, shifting back and forth on his heels
Argelia
"Indeed, I'm from High Rock, came here from Morrowind." He says, then chuckles, "Are you asking a Cartographer if he needs directions?" He laughs some, not trying to be rude, he just found it truly humerous. "I'm going to make a stop in Kynesgrove, then make my way to Windhelm." 

He smirks, "I've been to quite a few different places. Cyrodiil, Valenwood, and Elsweyr were the first places I visited. I studied in Cyrodiil, while waiting for them to finish part of my Envoy. Then visited Valenwood for work, same with Elsweyr. After Elsweyr we sailed to Morrowind, since I was looking for a talented blacksmith to forge some valuable metals I obtained as payment for a map I made for a Baandari Pedlar. And then I ended up here in Skyrim. It's a fine place, I suppose. Solitude reminds me a bit of Camlorn, for better or for worse."
Connie
Morrowind? Interesting. He'd go to say something along the lines of how he'd always wanted to travel to far places like that, but would be cut off, flushing and chuckling. Asking a map maker if he needs directions is like asking crops if they need water. He could find the humor in it though, laughing softly with the man

"Out of polite instinct" He'd offer, giving a small shrug like 'oh well, at least I tried'. "Windhelm? Oh, I'm actually coming from there myself. Ma insisted that I should leave the farm for a bit and go and see the world" 

Listening to the summery of the man's ventures put a wonderous sparkle in the dunmers eyes, nodding along as Damien spoke. "Afraid I've never been to either really, what's it like? I heard it's where all the pompous rich folk live eating off their platters if gold and forks of ivory" He waved his hand about like one reciting a child's tale, before tilting his head, sheepishly asking

"Say... Would, uhm... Your cartography need any help? If not then that's okay! And while I might be a bit green behind the ears, well, I'm eager to learn!" It was worth a shot, though he'd face palm slightly as he realized that he hadn't even introduced himself

"Jumping ahead just like Ma always says. I'm Darthan Sarano, it's a pleasure to meet you sir"
Argelia
"Usually the call to adventure comes from the soul, interesting that yours came from your mother." He says, "There's a lot worth seeing though, I agree with her judgement." 

"Solitude is quaint, Camlorn was a lot more *Pompous*, but Solitude has its moments of the same." He says, "They're fine enough, though. I'll always have a soft spot for Camlorn, it was my home some time ago. But now my home is The Storied Sail."

He smiles, "The Storied Envoy could always use more crew, it started as just the crew manning my ship for my mapmaking adventures, it has grown to be much more than that. Think of it like an Adventurer's Guild, we provide a bit of funding, as well as equipment and supplies, for people to adventure where ever we dock, and in return they help man our ships, as well as help out the locals wherever we end up." He chuckles, "The pleasure is all mine, I am Damien Antieve."