For the Argonian in Online, see Deep-in-Cups.
"Whoa, not so fast there, friend. You owe me money."

Deep-In-His-Cups is an Argonian who approaches the Dragonborn in a random encounter, during or after completing the "A Night to Remember" quest.


The Drunken Dare

He demands 10,000 Gold from the player, claiming that during their night of binge drinking, Sam Guevenne and the Dragonborn dared him to enter a Bandit camp and steal a hat, for which he would be compensated the aforementioned amount.

To resolve the issue, the Dragonborn can either pay him, talk him down to 750 (with Speech), intimidate him, or simply admit to not having the money. Selecting the last option will turn him hostile.

Ironically, the hat itself—which can be received by paying, pickpocketing or killing and looting him—is worth 1 Gold.


"Hey! There you are, you drunken bastard. I did it, so pay up."

Who are you? "We caroused together with Sam Guevenne, remember? We broke into the Temple of Dibella? How much did you end up drinking? You and Sam dared me to go into that bandit camp. Well I did and brought back his stupid hat like you said, so give me the 10,000 gold you promised."
I don't remember any of that. Be reasonable. (Persuade)
  • "Well... all right. Just because we are friends. Give me, say... 750 gold and we can call it even." (Success)
Here's your gold. (750 gold) "Thanks. You and Sam drink too hard for me. Think I'll take my gold and go buy a nice bit of swamp in Black Marsh."
Sorry, I don't even have 750 gold. "If there's one thing I hate more than a mean-spirited drunk, it's one who can't settle their debts."
  • "Nice try, but those bandits almost killed me. Now pay up." (Failure)
I'm not giving you anything. (Intimidate)
  • "All right... All right... Fine. I thought we were friends, but you're a real jerk, you know that?" (Success)
  • "Are you kidding me? I fought off all those bandits. I'm not afraid of you." (Failure)
Here's your gold. (10,000 gold) "Thanks. You and Sam drink too hard for me. Think I'll take my gold and go buy a nice bit of swamp in Black Marsh."
I don't have 10,000 gold. "So you're telling me you and Sam just sent me in there to die, then? I want my money, you bastard."


  • "We agreed to 750 gold. I want my money." —After succeeding in persuasion
  • "Hey, where do you think you're going? Come back here." —Walking away without paying him
  • "See you, friend. And take it easy on the wine." —After completing "The Drunken Dare"


  • Any gold paid to him will be available in his inventory for looting or pickpocketing.
  • His name, Deep-In-His-Cups, points to his tendency to drink heavily.
  • He is similar to the Madwoman and Sigar, in that they are all random encounters which occur some time after completing a Daedric quest.
  • After paying him, if followed and protected, he will travel to The Bee and Barb in Riften.


This section contains bugs related to Deep-In-His-Cups. Before adding a bug to this list, consider the following:

  1. Please reload an old save to confirm if the bug is still happening.
  2. If the bug is still occurring, please post the bug report with the appropriate system template  360  / XB1  ,  PS3  / PS4  ,  PC  / MAC  ,  NX  , depending on which platform(s) the bug has been encountered on.
  3. Be descriptive when listing the bug and fixes, but avoid having conversations in the description and/or using first-person anecdotes: such discussions belong on the appropriate forum board.
  •  PC   360   PS3   It is possible to encounter him more than once, even after he becomes hostile and is killed.
  •  360   PS3   If the Dragonborn claims to not have the money for him, and he becomes hostile, sheathing any drawn weapon can cause him to become neutral and walk away, saying "you are not worth it."
  •  360   He will occasionally respawn around 5 minutes after being killed and attack the player again. He does not respawn a third time.
  • Sometimes he will not speak and attack the player.
  • When followed from his initial encounter (if protected and prevented from death along the way) he will become stuck in a loop between Steamcrag Camp & Narzulbur.


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