Drowned Sorrows

Walkthrough
Only available after joining the Thieves' Guild. The quest is not tracked in the journal.

Talk to innkeeper Dagur after Talk to Ranmir about Haran, and ask about any other work. Apparently there is a good reason for Ranmir drinking, a woman he dearly loved named Isabelle Rolaine left with a thief named Vex.

Speak to Vex
Talk to Vex at the Ragged Flagon in Riften. It turns out Ranmir had tried to talk to Vex, but that did not yield much. Isabelle was trying to find something valuable quickly, and even though Vex did not think her up for such a job, pointed her towards Hob's Fall Cave.

Investigate Hob's Fall Cave
The Dragonborn travels to the cave, but tragically Isabelle never made it far in the cave. She is found dead with a letter on her body. See hated not having enough money to live and wanted to help Ranmir with her actions.

Hand Isabelle's letter to Ranmir
Return the letter to Ranmir who will be distraught, mentioning that he will have to think about all of this.

Ertränkte Sorgen