Persuasion Options (From UESP site)
What follows is a list of all persuasion attempts that can be made in Skyrim. Spoilers in this list are intentionally kept very minor. All speech challenges fall into one of five categories: Very Easy, Easy, Average, Hard, and Very Hard. Their skill requirements to pass are 10, 25, 50, 75, and 100, respectively. Possessing the Persuasion perk reduces the requirements on all but Very Easy challenges by 30%, dropping them to 10, 18, 35, 53, and 70, respectively. Wearing the Amulet of Articulation allows you to succeed at any persuasion check in the game regardless of skill.
Very Easy (10)†
World Persuading a shakedown bandit to leave you alone for 50 gold.
Markarth During The Forsworn Conspiracy, getting Margret to reveal information.
Redwater Den Getting a free sample from the attendant at Redwater Den.DG
Whiterun Persuading Loreius to help Cicero during Delayed Burial.
Falkreath Getting Lod to pay you 25 gold before searching for the dog during A Daedra's Best Friend.
Easy (25/18)
Quests
Winterhold The Black Star, convincing Nelacar that a priestess of Azura sent you.
Riften Caught Red Handed, getting the Mark of Dibella from Hofgrir Horse-Crusher.
Civil War Compelling Tribute, getting gold from Anuriel.
Civil WarCompelling Tribute, getting gold from Raerek.
Main quest A Cornered Rat, convincing Esbern to open his door.
Main quest Diplomatic Immunity, Getting the Thalmor guard to leave his post.
Markarth The Forsworn Conspiracy, getting information on Weylin from Mulush gro-Shugurz.
Markarth The Forsworn Conspiracy, getting Weylin's Key from Garvey.
College of Winterhold Good Intentions, getting the Augur of Dunlain's location from Mirabelle Ervine.
Solitude The Mind of Madness, getting the key to the Pelagius Wing from Erdi.
Markarth No One Escapes Cidhna Mine, getting skooma from Duach.
Riften Promises to Keep, getting Sibbi's key.
Riften Promises to Keep, persuade Louis Letrush to let you keep Frost.
Riften The Raid, getting Wujeeta to reveal where she gets skooma.
Main quest Season Unending, convincing Ulfric to join the peace talks.
Markarth The Taste of Death, getting Brother Verulus to follow you.
Solitude Tending the Flames, the first persuasion option when rewriting King Olaf's Verse.
Other
Windhelm After A Night To Remember, convincing Deep-In-His-Cups to accept a lower payment.
Riften Cooling down Dirge when talking about his name.
Solitude Convincing Irnskar Ironhand to forgive Octieve San's gambling debt.
Whiterun Convincing Mikael to leave Carlotta alone.
Markarth Convincing Mulush gro-Shugurz to treat his workers better.
Winterhold Convincing Ranmir to pay his dept to Haran.
Riften Convincing Riften's guard jailor that you're allowed to be wandering the jail.
Kynesgrove Convincing Roggi Knot-Beard to accept Iddra's charity.
Windhelm Convincing Torbjorn Shatter-Shield to pay his Argonian workers fair wages.
Solitude Convincing Captain Aldis to provide information about Angeline Morrard's daughter.
Solitude Convincing Vittoria Vici to wave the fee for Evette.
Rorikstead Getting Erik's father Mralki to purchase armor for his son.
Dushnikh Yal Getting Ghorbash the Iron Hand to join you as a follower.
Riften Getting information from Maul.
Riften Getting information on the meadery from Ungrien.
Riften Getting the Riften guards at the main gate to let you in.
Ivarstead Having Lynly Star-Sung in Ivarstead play you a song for free.
Dawnguard Selling Elder Scrolls to Urag gro-Shub for 3000 gold.
Average (50/35)
Quests
Markarth Buy Dwarven artifact, getting Calcelmo to pay you more.
Riften Caught Red Handed, convincing Indaryn to give you the Mark of Dibella.
RiftenCaught Red Handed, convincing Bolli to give you the Mark of Dibella.
Main quest Diplomatic Immunity, convincing Elisif the Fair to create a distraction.
Main questDiplomatic Immunity, convincing Igmund to create a distraction.
Main questDiplomatic Immunity, convincing Ondolemar to create a distraction.
Main questDiplomatic Immunity, convincing Siddgeir to create a distraction.
Main questDiplomatic Immunity, convincing Vittoria Vici to create a distraction.
Main quest The Fallen, convincing the Jarl of Whiterun to let you use Dragonsreach to capture a dragon.
Main quest A False Front, getting the innkeeper to tell you where the Imperial Courier is.
Main quest A False Front, getting the innkeeper to tell you where the Stormcloak Courier is.
Markarth The Forsworn Conspiracy, getting the key to Margret's room from Kleppr or Frabbi.
Markarth The Forsworn Conspiracy, getting Borkul the Beast to let you in to see Madanach.
Markarth The Forsworn Conspiracy, getting Rhiada to let you in to see Thonar Silver-Blood.
College of Winterhold Hitting the Books, convincing The Caller to let you take the books and leave.
Markarth The House of Horrors, convincing Logrolf that Boethiah sent you.
Riften/Ivarstead The Lover's Requital, getting Lynly to admit her true identity.
Markath A Night To Remember, getting Senna to reveal your next destination without cleaning the temple.
Whiterun A Night To Remember, getting Ysolda to reveal your next destination without getting her ring back.
Karthwasten Sanuarach Mine, convincing Atar to leave Karthwasten.
Karthwasten Sanuarach Mine, convincing Ainethach to sell the mine.
Main quest Season Unending, convincing General Tullius to join the peace talks.
Solitude Tending the Flames, the second persuasion option when rewriting King Olaf's Verse.
Riften Convincing Sapphire to forgive Shadr's debt during Stabilized.
Dawnguard Quests
Hunting the Monster, convincing a friend to help you find a vampire.
Lost to the Ages, convincing Katria you are strong enough to handle Arkngthamz.
A New Order, convincing Sorine Jurard to join Dawnguard without getting her a gyro.
Prophet, getting a carriage driver or innkeeper to give you information on the priest for free.
Other
Mor Khasgur Convincing Borgakh the Steel Heart to join you as a follower.
Riften Convincing Drahff and Hewnon to leave you alone in the entrance of the Ratway.‡
World Convincing a random thief to leave you alone.
World During a random encounter with a would-be mage, convincing him to give you his staff.
World During a random encounter with a mercenary, convincing them to give you the location they were heading to.
Hard (75/53)[edit]
Quests
Main quest During A Cornered Rat, getting Dirge to tell you the location of Esbern.
Main quest During A Cornered Rat, getting Vekel the Man to tell you the location of Esbern.
Main questDuring A Cornered Rat, getting Brynjolf to tell you the location of Esbern.
Rorikstead During A Night To Remember, convincing Ennis to reveal your next destination without finding his goat.
Whiterun During Dampened Spirits, getting Sabjorn to pay you half before the job.
Markarth During Hard Answers, tricking Calcelmo into giving you the key to the museum.
Riften During Loud and Clear, getting the key from Aringoth.
Whiterun During Missing In Action, getting information on Thorald Gray-Mane's location from Idolaf Battle-Born.
Winterhold During Onmund's Request, convincing Enthir to give you the amulet for free.
Morthal During Pieces of the Past, getting the hilt from Jorgen.
Riften During The Pursuit, convincing Vald to leave his guard post.
Main quest During Season Unending, convincing your favored side to accept a minor hold.
Thieves Guild/Solitude During Scoundrel's Folly, getting information from Gulum-Ei.
Windhelm During Summerset Shadows, getting Niranye to tell the truth.
Other
World Convincing a guard to ignore minor crimes.
Convincing Markarth guards to leave you alone, but even then you will still be taken to Cidhna Mine; it is one of the few speech checks in the game that always fails regardless of skill.
Very Hard (100/70)
Convincing Faralda to let you join the College of Winterhold without taking a test.
†
Very Easy speech challenges are unaffected by the Persuasion perk and have no failure dialogue. If you actually found a way to drop your Speech skill below 10, they would simply not appear in dialogue to even attempt.
‡
This persuasion challenge was cut from the game. These NPCs are instead always hostile to you
What follows is a list of all persuasion attempts that can be made in Skyrim. Spoilers in this list are intentionally kept very minor. All speech challenges fall into one of five categories: Very Easy, Easy, Average, Hard, and Very Hard. Their skill requirements to pass are 10, 25, 50, 75, and 100, respectively. Possessing the Persuasion perk reduces the requirements on all but Very Easy challenges by 30%, dropping them to 10, 18, 35, 53, and 70, respectively. Wearing the Amulet of Articulation allows you to succeed at any persuasion check in the game regardless of skill.
Very Easy (10)†
World Persuading a shakedown bandit to leave you alone for 50 gold.
Markarth During The Forsworn Conspiracy, getting Margret to reveal information.
Redwater Den Getting a free sample from the attendant at Redwater Den.DG
Whiterun Persuading Loreius to help Cicero during Delayed Burial.
Falkreath Getting Lod to pay you 25 gold before searching for the dog during A Daedra's Best Friend.
Easy (25/18)
Quests
Winterhold The Black Star, convincing Nelacar that a priestess of Azura sent you.
Riften Caught Red Handed, getting the Mark of Dibella from Hofgrir Horse-Crusher.
Civil War Compelling Tribute, getting gold from Anuriel.
Civil WarCompelling Tribute, getting gold from Raerek.
Main quest A Cornered Rat, convincing Esbern to open his door.
Main quest Diplomatic Immunity, Getting the Thalmor guard to leave his post.
Markarth The Forsworn Conspiracy, getting information on Weylin from Mulush gro-Shugurz.
Markarth The Forsworn Conspiracy, getting Weylin's Key from Garvey.
College of Winterhold Good Intentions, getting the Augur of Dunlain's location from Mirabelle Ervine.
Solitude The Mind of Madness, getting the key to the Pelagius Wing from Erdi.
Markarth No One Escapes Cidhna Mine, getting skooma from Duach.
Riften Promises to Keep, getting Sibbi's key.
Riften Promises to Keep, persuade Louis Letrush to let you keep Frost.
Riften The Raid, getting Wujeeta to reveal where she gets skooma.
Main quest Season Unending, convincing Ulfric to join the peace talks.
Markarth The Taste of Death, getting Brother Verulus to follow you.
Solitude Tending the Flames, the first persuasion option when rewriting King Olaf's Verse.
Other
Windhelm After A Night To Remember, convincing Deep-In-His-Cups to accept a lower payment.
Riften Cooling down Dirge when talking about his name.
Solitude Convincing Irnskar Ironhand to forgive Octieve San's gambling debt.
Whiterun Convincing Mikael to leave Carlotta alone.
Markarth Convincing Mulush gro-Shugurz to treat his workers better.
Winterhold Convincing Ranmir to pay his dept to Haran.
Riften Convincing Riften's guard jailor that you're allowed to be wandering the jail.
Kynesgrove Convincing Roggi Knot-Beard to accept Iddra's charity.
Windhelm Convincing Torbjorn Shatter-Shield to pay his Argonian workers fair wages.
Solitude Convincing Captain Aldis to provide information about Angeline Morrard's daughter.
Solitude Convincing Vittoria Vici to wave the fee for Evette.
Rorikstead Getting Erik's father Mralki to purchase armor for his son.
Dushnikh Yal Getting Ghorbash the Iron Hand to join you as a follower.
Riften Getting information from Maul.
Riften Getting information on the meadery from Ungrien.
Riften Getting the Riften guards at the main gate to let you in.
Ivarstead Having Lynly Star-Sung in Ivarstead play you a song for free.
Dawnguard Selling Elder Scrolls to Urag gro-Shub for 3000 gold.
Average (50/35)
Quests
Markarth Buy Dwarven artifact, getting Calcelmo to pay you more.
Riften Caught Red Handed, convincing Indaryn to give you the Mark of Dibella.
RiftenCaught Red Handed, convincing Bolli to give you the Mark of Dibella.
Main quest Diplomatic Immunity, convincing Elisif the Fair to create a distraction.
Main questDiplomatic Immunity, convincing Igmund to create a distraction.
Main questDiplomatic Immunity, convincing Ondolemar to create a distraction.
Main questDiplomatic Immunity, convincing Siddgeir to create a distraction.
Main questDiplomatic Immunity, convincing Vittoria Vici to create a distraction.
Main quest The Fallen, convincing the Jarl of Whiterun to let you use Dragonsreach to capture a dragon.
Main quest A False Front, getting the innkeeper to tell you where the Imperial Courier is.
Main quest A False Front, getting the innkeeper to tell you where the Stormcloak Courier is.
Markarth The Forsworn Conspiracy, getting the key to Margret's room from Kleppr or Frabbi.
Markarth The Forsworn Conspiracy, getting Borkul the Beast to let you in to see Madanach.
Markarth The Forsworn Conspiracy, getting Rhiada to let you in to see Thonar Silver-Blood.
College of Winterhold Hitting the Books, convincing The Caller to let you take the books and leave.
Markarth The House of Horrors, convincing Logrolf that Boethiah sent you.
Riften/Ivarstead The Lover's Requital, getting Lynly to admit her true identity.
Markath A Night To Remember, getting Senna to reveal your next destination without cleaning the temple.
Whiterun A Night To Remember, getting Ysolda to reveal your next destination without getting her ring back.
Karthwasten Sanuarach Mine, convincing Atar to leave Karthwasten.
Karthwasten Sanuarach Mine, convincing Ainethach to sell the mine.
Main quest Season Unending, convincing General Tullius to join the peace talks.
Solitude Tending the Flames, the second persuasion option when rewriting King Olaf's Verse.
Riften Convincing Sapphire to forgive Shadr's debt during Stabilized.
Dawnguard Quests
Hunting the Monster, convincing a friend to help you find a vampire.
Lost to the Ages, convincing Katria you are strong enough to handle Arkngthamz.
A New Order, convincing Sorine Jurard to join Dawnguard without getting her a gyro.
Prophet, getting a carriage driver or innkeeper to give you information on the priest for free.
Other
Mor Khasgur Convincing Borgakh the Steel Heart to join you as a follower.
Riften Convincing Drahff and Hewnon to leave you alone in the entrance of the Ratway.‡
World Convincing a random thief to leave you alone.
World During a random encounter with a would-be mage, convincing him to give you his staff.
World During a random encounter with a mercenary, convincing them to give you the location they were heading to.
Hard (75/53)[edit]
Quests
Main quest During A Cornered Rat, getting Dirge to tell you the location of Esbern.
Main quest During A Cornered Rat, getting Vekel the Man to tell you the location of Esbern.
Main questDuring A Cornered Rat, getting Brynjolf to tell you the location of Esbern.
Rorikstead During A Night To Remember, convincing Ennis to reveal your next destination without finding his goat.
Whiterun During Dampened Spirits, getting Sabjorn to pay you half before the job.
Markarth During Hard Answers, tricking Calcelmo into giving you the key to the museum.
Riften During Loud and Clear, getting the key from Aringoth.
Whiterun During Missing In Action, getting information on Thorald Gray-Mane's location from Idolaf Battle-Born.
Winterhold During Onmund's Request, convincing Enthir to give you the amulet for free.
Morthal During Pieces of the Past, getting the hilt from Jorgen.
Riften During The Pursuit, convincing Vald to leave his guard post.
Main quest During Season Unending, convincing your favored side to accept a minor hold.
Thieves Guild/Solitude During Scoundrel's Folly, getting information from Gulum-Ei.
Windhelm During Summerset Shadows, getting Niranye to tell the truth.
Other
World Convincing a guard to ignore minor crimes.
Convincing Markarth guards to leave you alone, but even then you will still be taken to Cidhna Mine; it is one of the few speech checks in the game that always fails regardless of skill.
Very Hard (100/70)
Convincing Faralda to let you join the College of Winterhold without taking a test.
†
Very Easy speech challenges are unaffected by the Persuasion perk and have no failure dialogue. If you actually found a way to drop your Speech skill below 10, they would simply not appear in dialogue to even attempt.
‡
This persuasion challenge was cut from the game. These NPCs are instead always hostile to you