"Hey! Saved you a beer, while you dealt with the Guild. Got the next job in hand?"

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After a successful run, it feels good to hop in on the local tavern and share a quiet one with the party. Even if the party is just a party of two. Life on the outskirts of the Kingdom is tough for everyone, adventurers included... and these are not the times to be picky about your partners. This Rogue has turned out to be better than most. When you met there weren't two copper to throw around between the two of you. A couple runs later and you can at least maintain your equipment and share a drink and a room at the Flipped Table.

You haven't done anything more complicated than exterminate some vermin or defend a few merchants on a trip to the next town over, nothing truly adventurous. But your both sure you'll be able to move on to more challenging stuff, once you get some more experience.

Better than most have. Better than both of you had before. This will be a true friendship if both of you survive.

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Final version of the one-eyed cat lady rogue. I saw a picture on Reddit about a one-eyed female cat that had been adopted by a better person than I. Originally it was going to be a Pirate themed piece, by I wasn't quite feeling it and it ended up being an unassuming one-eyed Cat-Lady drinking a beer in a Tavern. From there I got the idea of having her raising the mug as if toasting a new arrival and the setting for a D&D adventuring party was chosen almost on its own.
I wanted to draw how a rogue would look (leather/simple clothing, from light armour) while trying to avoid the dark/edgy stereotype of rogues. She's just a normal person with a tough life that gained some skills in trapping, sneaking and liberating your purse of excess weight, that doesn't make her an asshole. That lack of an eye would give her issues with depth perception so the fact that she's still alive and a rogue let's you know she's good.