Cynthia
Laerian smirks. He sure was proud of his job— like she was, kind of. She was proud that she got paid to kick ass, while many others worked some boring, random job that didn't come with the perks of being able to fight people. Why live?

"Do you have any long term goals after you became jobless?" Laerian asks, a hand on her chin. Maybe she would try drinking a bit today. It just felt like that kind of night, when it was easier to enjoy a drink. Seeing that the man wasn't drinking anymore, she doubts that she would find it any more appealing than he did, though.
Billy
"Becoming jobless came as a suprise to me, I wasn't expecting to be forced into exile so I never really thought about it. Usually someone like myself works a single job their entire lives and I was never one for thinking ahead anyway" 

The Elf did raise a good point though, he wasn't going to become a servant again. While the circumstances surrounding his change in occupation weren't the best he wasn't going to ignore what fate had seemed to drop in his lap. "Figured I might try my luck adventuring people always seem to be looking for others that are willing to solve their problems for cheap"
Cynthia
"It's a nice job for people with big hearts or... To be blunt, stupid people. I think you'd be the first, if I really had to place you on that scale. Putting your life on the line every day usually has to come with a lot of resistance to emotional and mental worries. Some people are strong enough to stride through that, some are just blissfully unaware. Or they just adventure for the sake of adventuring. There aren't a strict two groups, or three, that you can put them in."

Laerian got kinda wordy there, for some reason. She seemed pretty compelled to talk about this topic, as adventuring had always been a part of her life. Moving through roads and cities— meeting new people, maybe trying new things. All of that had become a part of her life now.

"It's fun, though. It's fun."
Billy
"Don't get the wrong Idea, adventuring just seems like decent pay without many questions asked something that I won't deny benefits me immensely"

Laerian did have a point though. Tobias knew he was in a unique situation, having no allegiance and nobody to look after apart from himself made him a perfect candidate for a job with high risk of death more so then someone with people they need to take care of anyway. 

"I should try and find a place to stay for the night, then try this guild you mentioned in the morning. Hopefully I can find it"