|Primary Skills||Alchemy, Enchanting, Smithing, Archery, Light Armor, One-handed, Sneak, Speech|
He wears a set of hide armor with a matching helmet, pair of boots, and bracers. He has two weapons in his possession: one a leveled mace which can be up to Daedric in quality, the other an iron dagger.
Deep-In-His-Cups will approach you in a familiar, friendly manner: "Hey! There you are, you drunken bastard. I did it, so pay up." Attempting to just walk away from him will have him call to you to come back: "Hey, where do you think you're going? Come back here." If you tried to walk away, his second greeting will be a bit less friendly: "Whoa, not so fast there, friend. You owe me money." Asking him who he is will have him respond: "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."
At this point, you will be given multiple options towards how to resolve this predicament. You can attempt to persuade him that he's being unreasonable, and if this is successful, you will get him to lower the debt at 750 gold. You can attempt to intimidate him into ignoring your debt, which will make him give up on collecting the debt if you succeed. You can also just pay up, or decline and make him hostile towards you. If you pay him (either 10,000 or 750 septims), Deep-In-His-Cups gives you the 1 septim hat, then leaves for Black Marsh, or to buy something for his headache.
|I'm not giving you anything.
|Succeed: All right... All right... Fine. I thought we were friends, but you're a real jerk, you know that?|
|Fail: Are you kidding me? I fought off all those bandits. I'm not afraid of you.|
|I don't remember any of that. Be reasonable.
|Succeed: Well... all right. Just because we are friends. Give me, say... 750 gold and we can call it even.|
|Fail: Nice try, but those bandits almost killed me. Now pay up.|
|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.
If there's one thing I hate more than a mean-spirited drunk, it's one who can't settle their debts.
|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.|
|750 Gold Thanks. You and Sam drink too hard for me. Think I'll take my gold and go buy something for this headache.|
If you try to walk away after talking him down to 750 gold, he will pursue you and remind you of this: "We agreed to 750 gold. I want my money." Trying to speak to him after you paid him will have him happily say goodbye, once more: "See you, friend. And take it easy on the wine."
- No matter how you opt to deal with Deep-In-His-Cups, he will continue to randomly spawn every once in a while, and make the same demands as before. To avoid paying large amounts of money over time, your best option is to kill him every time you encounter him.
- This bug is fixed by version 1.2.4 of the Unofficial Skyrim Patch.
- If you attack him and then yield, he won't demand the money again, making this an alternate way to get out of paying besides killing him.