According to the innkeeper, Ranmir used to be a happy and cheerful person, as he was in love with a woman named Isabelle Rolaine. After his lover left him, he became depressed by this and became an alcoholic. He spends most of his time at the local inn, The Frozen Hearth, drowning his sorrow.
The Dragonborn can offer Ranmir an alcoholic beverage.
Haran gives a side quest to convince Ranmir to pay his bar tab, which can be done with speech challenge, or by offering to pay the tab for him. Haran might give the quest even if Ranmir is dead. This side quest is required in order to progress to the next part of Ranmir's story.
When spoken to, the innkeeper asks the Dragonborn to find out what happened to Ranmir's lover, Isabelle Rolaine, because he doesn't like the state Ranmir is in (Note: This task does not show up in the quest journal).
Talking to Haran reveals that, one night, when the inn ran out of Honningbrew Mead, Ramnir flew into a rage. He said that Isabella ran off with a thief named Vex, who lives in Riften. Ranmir will have nothing useful to say on the matter. Vex can be found in the Ragged Flagon; she will speak to the Dragonborn regardless of whether or not they've gained entry to the Thieves Guild.
Talking to Vex reveals that Isabelle wanted to make some money, but that Vex didn't believe she was capable of it. Isabella refused to be turned away, however, so Vex sent her to Hob's Fall Cave. Despite her misgivings, Vex seems to have expected her to make it back to Ramnir safely.
Upon traveling to Hob's Fall, the Dragonborn discovers her corpse, along with a letter written for Ranmir explaining her intentions. The letter appears to have been written as if it was meant to be sent before she set off for Hob's Fall.
Taking the letter and giving it to Ranmir gives him closure on his lover's death. After receiving this news, Ranmir states that he needs to think about things; afterwards, he ceases drinking excessively.
- "Unless you're bringing me another round, you can just keep walking."
- "I got nothin' to say to you."
Birna "We need coin, Ranmir, and you're not bringing home any."
Ranmir "And you would have me do what, join the College and prance around casting spells all day?"
Birna "Don't just walk away from me! Where do you think you're going?"
Ranmir "To the Inn for a drink, of course! Where else could I even go in this gods forsaken town?"
Birna "And what, you think that'll solve all your problems?"
Ranmir "Probably not, but it's worth a try!"
Birna "Please, come home. Just...come home."
Ranmir "Can't. Got at least two rounds to go. Why don't you go...sell something?"
Birna "Why? Because I'd rather be here trying to keep my only brother from drinking himself to death."
Ranmir "Ha! Drink ain't gonna kill me. Not today, anyway."
- It is possible for him to be killed during the College of Winterhold questline. During the fight with Ancano to neutralize the Eye of Magnus, the Magic Anomalies attacking the town may kill Ranmir.