Midha Aenoch (cloudgazer) is a 30-year-old dwarven Grey Warden who used to run with the Carta and other criminal gangs in the Free Marches. She's all about the drinking and gambling, so she could have run into him during her travels? It doesn't sound like he traveled much outside of Markham until after he left the Free Marches, but since when she was in the Carta she was a smuggler, very likely she wound up in Markham a few times! About nine years ago she became dead to the Carta, so she didn't really go too much outside of Kirkwall and Starkhaven, but there's a time period at the 7 years ago mark where she traveled between Kirkwall to Starkhaven and could have possibly detoured to Markham maybe? Otherwise, I think that if he still gambles and drinks, they could meet in Cumberland and would probably be friends, from the sounds of it! She only does superficial friendships due to her lifetime of crime (she finds that forming Real Bonds is a Bad Idea for many reasons), but she's a friendly person who loves fun (and hates being a Warden lmao oops but her coping method atm is just to pretend like it's not a thing and ignore the problem).
My other character is this guy, Sorin Ghrian, a 25-year-old City Elf who is probably way too happy considering his life circumstances (elf in human world, amputated right arm due to systematic racism, etc) but being happy is also his coping mechanism for the hardships of life. He's also a naive little cinnamon roll. He works at a high-end clothing store called Brouillard's Clothiers in the marketplace, trains in swordsmanship on the down-low with someone who has/had Orlesian noble connects (though Sorin himself doesn't know this, he only suspects that he's Orlesian based on his accent when he's not trying to mask it), and can otherwise be found window-shopping in the marketplace (mostly at clothes) or in elf-friendly taverns NOT drinking or gambling since he hates alcohol and would rather spend what little extra spending money he has on clothes BUT is usually there because he likes people, particularly people who aren't racist assholes. ;;; Maybe they can run into each other at some point, idk, but the family Ellie works for would know Sorin's mentor and would probably be aware of the scandal he left behind, idk if Ellie would too but we can discuss!
Can't wait to see you and your character in play!!