I completed two Daedric quests before starting A Night to Remember, both of which were morally uncomplicated. The first, The Break of Dawn, required me to clear out the draugr and necromancers from Meridia's Temple. Because I fight those two hostile groups very frequently, I had no problem doing so at the behest of a Daedric Prince. Besides, Meridia is one of the few "good" Daedra, so there was no real conflict for me. The second, The Mind of Madness, required me to track down Sheogorath inside the mind of an insane, deceased Emperor and convince him to vacate. While Sheogorath, as the Daedric Prince of Madness, is unpredictable at best, the whole surreal quest occurs inside an NPC's mind, so none of the actions are "real" (i.e., taking place in Skyrim).
A Night to Remember, however, provided more opportunities for moral conflict. The quest began when I accepted a drinking challenge from a stranger in Whiterun's The Bannered Mare. The stranger, Sam Guevenne, bet me his staff that I couldn't drink him under the table. While a drinking contest might not seem like a morally sound scenario, it is well to remember that Skyrim is a hard-drinking culture; "milk-drinker" is a standard insult. I soon blacked out and woke up in the Temple of Dibella in Markarth -- a town I had not visited before, and did not remember visiting now. Apparently, I had trashed the place in my drunken stupor, and the priestess was demanding that I help her clean up, which I did...after I failed to Persuade my way out of it. She then mentioned the town of Rorikstead, where Sam and I had apparently caused even more trouble. When I arrived, I was accosted by the farmer Ennis, who claimed that I had stolen his goat and sold it to Grok the Giant. After failing again to Persuade a victim of the previous night's shenanigans, I peaceably lured Gleda the goat back to Ennis. He then told me that I owed my friend Ysolda of Whiterun some money. I traveled to Whiterun and spoke to Ysolda, who told me that she gave me a wedding ring on credit, but apparently my fiancee (whoever that was) and I had some sort of falling out, and she had gone back to where we met: Witchmist Grove. I needed to pay for the ring or go get it back from my intended; this time, however, I managed to Persuade her to let me slide on my debt. While laughing good-naturedly at my drunken stupidity, she informed me that I was supposed to get married at a place called Morvunskar.
Morvunskar, as it turned out, was an abandoned fort, full of hostile wizards. I fought my way through them, thinking that Sam and/or my mystery bride might be hostages. What I found, however, was a glowing portal to what looked like an evening garden party. When I found the main banquet table, I encountered not my betrothed, but Sam -- who quickly revealed himself to be Sanguine, Daedric Prince of Debauchery. The whole quest, it seemed, was an elaborate prank for his amusement. For my troubles, he made good on his original wager; he gave me Sanguine's Rose, a powerful staff indeed, then transported me back to the Bannered Mare.
A Night to Remember is certainly one of the more light-hearted quests available in the game, but it still offered a few moral decision points. As with all quests, Daedric or not, it is always possible to turn down, purposely fail, or refuse to complete a quest at any point. Had I not felt like dealing with the aftermath of my carousing, I could have just walked away from the temple in Markarth and gone on to other things. Additionally, with each interaction, my dialogue options included Persuade, Intimidate, Bribe (sometimes), or just do the thing I was asked to do. As I explained in a previous post, I usually prefer Persuade to Intimidate, and Intimidate to Bribe. For this quest, however, it felt wrong to go past Persuade; I obviously had given these three people a rough time the previous night, so if I couldn't talk myself off the hook, I didn't feel right threatening them or buying them off.
The tasks themselves were a mixed bag. Cleaning the temple was tedious, but easy. Finding the goat, on the other hand, was much trickier, both strategically and morally. According to Ennis, I sold Gleda to Grok, so fighting the giant seemed both wrong and foolish. I opted instead for stealth, luring Gleda away while keeping my distance from Grok and his cyclopean club. Because I used Persuade successfully on Ysolda (who was probably still grateful for the mammoth tusk I found for her earlier), I unwittingly skipped the very last task.
According to the walkthroughs, if I had failed to Persuade Ysolda, she would have required me to go to Witchmist Grove to reclaim the wedding ring. After I finished the quest, I felt a bit guilty about talking Ysolda into cancelling my debt, and I was curious about the woman to whom I had proposed, so I traveled to the aforementioned Grove. There I met my fiancee:
The other problematic aspect of this quest is the fact that I had become the pawn of a more powerful being without my consent. The two previous Daedric quests avoided this issue -- the first by allowing me to chose a quest already in alignment with my established habits, the second by being done at the behest of a worshipper, rather than the being itself. A Night to Remember rewarded me for jumping through a Daedric Prince's hoops, and I did not like the feeling.