Gentleman, 3rd Variant (5e Class)

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Gentleman

Respectful to all of the female gender. These men often use their guile and charm to gain the respect of the fairer sex. While otherwise kind-hearted and gentle a gentlemen may chastise those that disrespect a woman. Those that bring harm to them are infinitely worse.

Gentlemen have perplexing views on relationships with women. Is it okay to have a crush on women? Why does she make my pee-pee feel tingly when we are close? Are French maids NSFW? Truly worrisome and nerve-wracking questions that all gentlemen should at one point ask themselves. After centuries upon centuries of polished and refined gentleman knowledge and wisdom, it has been decided that it depends. It is believed that if the woman reciprocates the feelings on having a crush, it is alright. If she does not however, it is a terrible offence. It is believed that our pee-pees becoming tingly whenever women we really like come close to us that it is simply the gods showing us the horrors of temptation. Are French Maids NSFW? Yes. Yes they are.

But what makes a gentleman a gentleman? Well. To be a gentleman, one must follow the acronym S.I.M.P.

• S imply.
• I dolize.
• M y.
• P rincess.

For every maiden, no matter what shape and size, truly must be respected for you to have some sense of dignity.

A Gentleman Knight escorting a maiden.

Creating a Gentlemen

You can make a gentleman quickly by following these suggestions. First, Charisma should be your highest ability score, followed by Strength. Second, choose the Noble background. Third, choose a diplomats pack.

Class Features

As a Gentlemen you gain the following class features.

Hit Points

Hit Dice: 1d10 per Gentlemen level
Hit Points at 1st Level: 10 + Constitution modifier
Hit Points at Higher Levels: 1d10 (or 6) + Constitution modifier per Gentlemen level after 1st

Proficiencies

Armor: Light armor
Weapons: Simple Weapons and Rapier
Tools: Choose one type of artisan’s tools and one musical instrument
Saving Throws: Strength and Charisma
Skills: Choose any two

Equipment

You start with the following equipment, in addition to the equipment granted by your background:

• Any simple weapon
• (a) A diplomat’s pack or or (b) An entertainer's pack
• A monocle, and a pocket watch
• Leather armor

Table: The Gentlemen

Level	Proficiency Bonus	Features	Fisticuffs Bonus
1st	+2	Anger of The Gentlemen, Oath of Chivalry, Fisticuffs, Unarmored Defense	1d6
2nd	+2	On My Honor, After You	1d6
3rd	+2	Jack of All Trades, Man of Many Hats	1d6
4th	+2	Ability Score Improvement	1d6
5th	+3	A Man's Duty, Extra Attack, Looks That Kill	1d8
6th	+3	Challenge, Man of Many Hats	1d8
7th	+3	Roll Up the Sleeves	1d8
8th	+3	Ability Score Improvement	1d8
9th	+4	Simp Sense™	1d10
10th	+4	Dashing Rogue, Man of Many Hats	1d10
11th	+4	Extra Attack	1d10
12th	+4	Ability Score Improvement	1d10
13th	+5	The Ol’ One, Two	2d6
14th	+5	Man of Many Hats	2d6
15th	+5	Handsome Devil	2d6
16th	+5	Ability Score Improvement	2d6
17th	+6	Cleaning House	2d8
18th	+6	Man of Many Hats	2d8
19th	+6	Ability Score Improvement	2d8
20th	+6	Don't touch my lady, you filthy villain	2d8

Anger of The Gentlemen

While in combat, whenever a female ally takes damage it forces a gentlemen into a state of which all wise men fear. When a friendly female creature takes damage you may use your reaction to make an attack at a creature within reach using your fisticuffs.

Oath of Chivalry

As long as a creature has a gender you are able to determine whether or not it is female.

As a Gentlemen you vow to uphold and respect women. If you willingly strike a woman without cause, you may not use any of your class features until you have formally, and graciously apologized to the woman that you wronged.

Fisticuffs

As a gentlemen you are obligated to use your bare fists to solve disputes. Due to using them extensively you, as a gentlemen are adept at using your Fisticuffs.

At 1st level, your unarmed strikes are more effective than the average Joe's.

You gain the following benefits while you are unarmed and you aren’t wearing medium or heavy armor or wielding a shield:

• You can choose Strength or Dexterity for your attack and damage rolls.
• You can roll a d6 in place of the normal damage of your unarmed strike. This die changes as you gain gentlemen levels, as shown in the fisticuffs bonus column of the gentlemen table.
• When you make a bonus attack, you may use your unarmed strike.

Unarmored Defense

Starting at 1st level when you are not wearing any armor or using a shield your AC is equal to 10 + your strength modifier + your charisma modifier.

On My Honor

At 2nd level and on, when you or one creature within 60 feet of you who can hear you, makes a skill check or save, you may add your Fisticuffs bonus die to it. You must decide to use this ability before the roll is made. You must take a short or long rest to use it again.

After You

At level 2, after Initiative is rolled you may swap initiative with another friendly creature as long as they rolled lower than you.

Jack of All Trades

At 3rd level, you can add half your proficiency bonus, rounded down, to any ability check you make that doesn’t already include your proficiency bonus.

Man of Many Hats

Starting at 3rd level as a gentlemen you have many roles to fill in the world you live in.

At level 3 you gain your first Hat, you choose one from the following Hats: The Holy Man, The Duelist, The Minstrel, The Pugilist, The Proverbial Assaulter, or The Adept. Your choice grants you features at 3rd level and again at 6th, 10th, 14th, and 18th level.

You gain an additional hat at level 10, at level 14, and another at level 18. Treat this hats like your normal level

Spellcasting Ability

Charisma is your spellcasting ability for your Gentleman spells, since their power derives from the strength of your personality. You use your Charisma whenever a spell refers to your spellcasting ability. In addition, you use your Charisma modifier when setting the saving throw DC for a Gentleman spell you cast and when making an attack roll with one.

Spell save DC = 8 + your proficiency bonus + your Charisma modifier

Spell attack modifier = your proficiency bonus + your Charisma modifier

Ability Score Increase

When you reach 4th level, and again at 8th, 12th, 16th, and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

Extra Attack

Beginning at level 5, you can attack twice, instead of once, whenever you take the Attack action on your turn. You can attack three times at level 11.

Looks That Kill

At level 5 as a Gentlemen you can use your killer looks to impose a threat on your target. Your attacks score a critical hit on a roll of 19 or 20. At 15th level your attacks score a critical hit on a roll of 18-20.

A Man's Duty

At level 5, your unarmed strikes count as magical for the purpose of overcoming resistance and immunity to non-magical attacks and damage. While in combat you may use your charisma modifier for your melee attack rolls and damage bonuses rather than your strength or dexterity. At level 15 while in combat you can add your charisma modifier with your strength (Or dexterity if using a Finesse Weapon.) to your attack and damage rolls.

Challenge

At level 6 as a bonus action you may challenge a creature within 10ft of you that can either see or hear you. The target must make a Wisdom saving throw against your Gentlemen spell save DC. On a failed save, the target has disadvantage on all attack rolls against targets other than you until the end of your next turn.

Roll Up The Sleeves

At level 7 you gain the ability to roll up your sleeves to use your hands more effectively. While your sleeves are rolled up your Dexterity Score is equal to your Charisma Score. You may only have your sleeves rolled for a maximum of thirty minutes before you become annoyed and uncomfortable and roll them back down. After a short rest, you may roll up your sleeves again.

Simp Sense™

At 9th level, your experience and borderline mystical tendencies to protect women have expanded. You are now able to detect whenever a damsel is in distress within a 100ft radius. You know the exact location, but cannot tell what exactly is occurring without prior knowledge or investigation.

At 18th level, as an action, while you are within 20 feet of a female friendly creature you may have her use her reaction to make an attack action and move up to her speed.

Dashing Rogue

At level 10 choose two of your skill proficiencies. Your proficiency bonus is doubled for any ability check you make that uses either of the chosen proficiencies. Your movement speed is also increased by 10 feet.

Hat Trick

At level 10 as an action, you may switch hats. When you switch hats you may not use class features granted by that hat until your next long rest.

The Ol’ One, Two

At level 13, Once while your sleeves are rolled up after you deal damage using your fisticuffs, you may choose to inflict more damage to the same creature. When you choose to give them "The Ol' One Two", the creature you attacked receives additional damage equal to twice your Fisticuffs Bonus.

Handsome Devil

At Level 15 your charm raises to supernatural levels. Add 4 to your Charisma score up to a maximum of 24.

Cleaning House

At 17th level, when you score a critical hit you may roll an additional damage die. Additionally on your turn, if you score a critical hit and reduce a creature to 0 hit points, you may attack another creature within range with your fisticuffs.

Don't touch my lady, you filthy villain

At 20th level, whenever a female creature gets attacked, affected by a status ailment, or any sort of detrimental feature/effect within a 30ft radius, you gain one additional unarmed attack.

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The Haberdashery

Below is a list of hats and what they do.

The Pugilist

The Hatless style, Gentlemen are known for being good at fighting with their bare hands. Not wearing a Hat gives you more liberty of movement. You gain the following class features while being the Pugilist.

Level 3: The Classic Combo: Immediately after you take the Attack action on your turn, you can make two unarmed strikes as a bonus action.

Once you use this feature, you must finish a short or Long Rest before you can use it again.

Brace Up: You can use a reaction to brace for attacks. Roll your fisticuffs die + your gentleman level + your Constitution modifier and gain that many temporary hit points.

Once you use this feature, you must finish a short or Long Rest before you can use it again.

Fancy Footwork: You gain proficiency in Dexterity saving throws.

Level 6: Dempsey Roll: Before you make an attack that does not already have disadvantage, you can declare you are swinging successive hooks. You make all weapon attack rolls until the end of this turn with disadvantage and when you deal damage with an unarmed strike you do not roll for the weapon’s damage die, but use the maximum die result instead.

Stronger for my lady: Your carrying capacity is doubled, and when you deal damage with a melee weapon or unarmed strike to an inanimate object that damage is doubled. Your standing jump distance is the same as your running start jump distance.

Level 10: Improved Extra Attack: You can Attack an additional time whenever you take the Attack action on your turn.

Level 14: Prove My Worth: When you Roll Up The Sleeves, you add your proficiency bonus to your damage with unarmed attacks and pugilist weapons for the next minute. You can use this feature again after you complete a long rest.

Never let a lady down: When you are reduced to 0 hit points, but a lady is seeing you fight, you regain half of your maximum hit points, and gain a level of exhaustion. You cannot use this feature again until you finish a long rest.

Level 18: You can use the class features Brace Up and The Old One-Two twice before a rest, but only once on the same turn.

The Adept

Wearing this pointed hat allows your good looks to manifest as elemental powers. You gain the following class features while wearing the Adept's Hat. You gain the following spells while you are wearing this hat. You may cast each spell (except Cantrips) only once before needing a long rest.

Spells Known at Gentlemen Level 3

• Cantrip: Acid Splash, Fire Bolt, Ray of Frost, Shocking Grasp
• Level 1: Burning Hands, Detect Magic, Magic Missile, Thunderwave
• Level 2: Gust of Wind, Scorching Ray

Spells Known at Gentlemen Level 6

• Cantrip: Chill Touch
• Level 2: Darkness
• Level 3: Fireball, Lightning Bolt, Sleet Storm

Spells Known at Gentlemen Level 10

• Cantrip: Poison Spray
• Level 4: Ice Storm, Stoneskin, Wall of Fire
• Level 5: Cone of Cold, Wall of Stone

Spells Known at Gentlemen Level 14

• Level 5: Cloudkill
• Level 6: Chain Lightning
• Level 7: Delayed Blast Fireball

Spells Known at Gentlemen Level 18

• Level 8: Earthquake
• Level 9: Meteor Swarm

The Duelist

The Hat Most Gentlemen are known for, The Top Hat. Putting this hat on your head allows for more versatile combat techniques. You gain the following class features while wearing the Duelist's Hat.

Level 3: Dueling: When you are wielding a melee weapon in one hand and no other Weapons, you gain a +2 bonus to Damage Rolls with that weapon.

Second Wind: You have a limited well of stamina that you can draw on to protect yourself from harm. On Your Turn, you can use a Bonus Action to regain hit points equal to 1d10 + half your Gentlemen level. Once you use this feature, you must finish a short or Long Rest before you can use it again.

Level 6: Action Surge: You can push yourself beyond your normal limits for a moment. On Your Turn, you can take one additional action on top of your regular action and a possible Bonus Action.

Once you use this feature, you must finish a short or Long Rest before you can use it again.

Level 10: Improved Extra Attack: You can Attack an additional time whenever you take the Attack action on your turn.

Level 14: Indomitable: Beginning at 9th level, you can reroll a saving throw that you fail. If you do so, you must use the new roll, and you can't use this feature again until you finish a Long Rest.

Advanced Dueling: When you are wielding a melee weapon in one hand and no other Weapons, you gain a +2 bonus to Damage Rolls with that weapon. This stacks with the class feature Dueling.

Level 18: You can use the class features Action Surge and Indomitable twice before a rest, but only once on the same turn.

The Minstrel

Wearing this Feathered hat allows your singing merit to take a form giving you the insight into odd things and songs to go with them! You gain the following class features and spells while wearing the Minstrel's Hat depending on your Gentlemen level. You may cast each spell only once before needing a long rest.

Spells Known at Gentlemen Level 3

• Cantrip: True Strike, Light, Message
• Level 1: Bane, Sleep
• Level 2: Blindness/Deafness

Spells Known at Gentlemen Level 6

• Level 2: Hold Person
• Level 3: Tiny Hut

Spells Known at Gentlemen Level 10

• Level 4: Confusion
• Level 5: Hold Monster

Spells Known at Gentlemen Level 14

• Level 5: Legend Lore
• Level 6: Irresistible Dance
• Level 7: Teleport

Spells Known at Gentlemen Level 18

• Level 8: Mind Blank
• Level 9: Foresight

Level 3: Song of Rest: You can use soothing music or oration to help revitalize your wounded allies during a Short Rest. If you or any friendly creatures who can hear your performance regain hit points by spending Hit Dice at the end of the Short Rest, each of those creatures regains an extra Hit Points equal to your Fisticuffs bonus.

Level 6: Song of Honor: You may use the On My Honor class feature two additional times between rests.

Level 10: Words of Wisdom: You may add 1 spell from the Adept or Holy Man Spells Known List to the Minstril Spells Known list. They keep their level requirements and spell level.

Level 14: Ballad of Honor: You may use the On My Honor class feature two additional times between rests. This stacks with the class feature Song of Honor

Level 18: Words of Wisdom: You may add 1 more spell from the Adept or Holy Man Spells Known List to the Minstril Spells Known list. They keep their level requirements and spell level.

The Holy Man

This hat bears the markings of a holy symbol. Allowing your good willing heart to provide divine aid. You gain the following class features and spells while wearing the Holy Man's Hat. You may cast each spell only once before needing a long rest.

Spells Known at Gentlemen Level 3

• Cantrip: Spare the Dying, Sacred Flame
• Level 1: Cure Wounds, Healing Word
• Level 2: Gentle Repose

Spells Known at Gentlemen Level 6

• Level 2: Prayer of Healing
• Level 3: Speak with Dead

Spells Known at Gentlemen Level 10

• Level 4: Banishment, Death Ward
• Level 5: Mass Cure Wounds

Spells Known at Gentlemen Level 14

• Level 5: Raise Dead
• Level 6: Heal
• Level 7: Resurrection

Spells Known at Gentlemen Level 18

• Level 8: Antimagic Field
• Level 9: Mass Heal

Level 3: Turn Undead: As an action, you can speak a prayer censuring the Undead. Each Undead that can see or hear you within 30 feet of you must make a Wisdom saving throw. If the creature fails its saving throw, it is turned for 1 minute or until it takes any damage.

A turned creature must spend its turns trying to move as far away from you as it can, and it can't willingly move to a space within 30 feet of you. It also can't take reactions. For its action, it can use only the Dash action or try to escape from an effect that prevents it from moving. If there's nowhere to move, the creature can use the Dodge action. When you use Turn Undead you must then finish a long Rest to use it again.

Level 6: Hands of Life: When you restore hit points to a creature using a touch spell you add your Fisticuffs bonus to the amount healed.

Level 10: Co-Operative Healing: The Healing Spells you cast on others heal one additional creature of your choice within the spell's range.

Level 14: Divine Fists: You gain the ability to infuse your Fisticuffs with divine energy. Once on each of your turns when you hit a creature with a Fisticuffs attack, you can cause the attack to deal an extra 2d8 radiant damage to the target.

Level 18: You can use your Turn Undead one more time between rests. When you finish a short or Long Rest, you regain your expended uses.

The Proverbial Sentinel

Wearing this dapper hat brings your words to a new level of influence! Instead of going out of your way to injure and physically harm your opponents, you can instead choose to settle a quarrel by defeating them emotionally. You gain the following class features and spells while wearing the Minstrel's Hat depending on your Gentlemen level. You may cast each spell only once before needing a long rest.

You cannot roast women unless they have committed an action of the evil alignment.

Level 3: You gain the ability to initiate a roast. As a gentleman, you have come to the conclusion that not all disputes can be solved by fisticuffs. Perhaps it is sometimes better to harm them emotionally, rather than physically. Roasting has several special properties, as seen here:

Initiation:

• When you initiate a roast, you must declare that you are going to do so.
• When a roast is initiated roll the table of array as many times as your charisma modifier, each roll is with disadvantage unless you planned this your last long rest.
• Each roll must be used in order, including the ones from your last long rest assuming you planned this.
• If your opponent accepts the challenge, they can also roll the table as many times as their charisma modifier with disadvantage.
• If your opponent ignores, dissuades, or rejects the challenge, you roast as normal. They do not get to roll insults however.
• This is usually not considered enough to start a physical fight, unless used mid-combat.

Performance:

• When you use an insult, roll 1d20 + your charisma and wisdom to land the remark.
• Gentlemen 3rd variants add their proficiency to the insult damage as they are proficient in insults.
• If your opponent has under 10 intelligence they take half damage.
• If your opponent has over 20 intelligence they take double damage.
• If either party runs out of insults, they can roll the table an amount of times equal to their charisma modifier.
• However, when rolling new insults they must succeed a DC 15 wisdom save to avoid writer's block.
• Gentlemen, 3rd Variants get to add their proficiency to the wisdom save.

Comeback:

• If an insult is slung at anyone, they can roll the Array of Comebacks with disadvantage (unless they are also a Gentleman, 3rd Variant).
• This can only be done once until the end of your next turn.
• To use a comeback, roll 1d20 + your wisdom and strength to land the response.
• If your opponent has under 10 intelligence they take half damage.
• If your opponent has over 20 intelligence they take double damage.

Conclusion:

• The Roast ends when either party is at 0 HP.
• The Roast can also end if one party forfeits or surrenders.
• The loser of the Roast is deeply embarrassed and humiliated.
• For both parties: if you are reduced to 0 HP in a roast, you stumble out of the roast dazed and confused on 1 HP.

Insecurity Investigation

Every roasting session starts off with a strong insult. One that particularly stings. But it is not easy to come up with one, as such it must be determined via careful observation. The better the insult, the more powerful it becomes. Upon plotting the start of a roast, roll the Array of Insults table three times with advantage at the end of a long rest. This shall have you prepared for the assault. As being the expert of insults that you are, you can choose to add or not add proficiency to your rolls.

1d8	Array of Insults
1	Nothing: You couldn't think of anything.
2	Irrelevant: You think of something that is mildly irrelevant. When using this insult, you gain a disadvantage on your next roll, regardless if it's a skill check, an attack roll, or a saving throw. Deal 1d4 psychic damage.
3	Insecurity: You come up with an insult that stabs right into your opponent's insecurities, as such, you and your allies may add your proficiency bonus to your next Intimidation check. Deal 1d4 + charisma psychic damage.
4	Hurtful: You think of an insult that pertains directly to your opponent's background, race, class, or personality, when used your opponent gains disadvantage on their next roll. Deal 2d4 psychic damage.
5	Witty: You think of a clever and potentially comedic insult, (and perhaps make the observers laugh.). When using this chide, you and your allies may add your proficiency bonus to your next Persuasion check. Deal 2d4 + charisma psychic damage. DC15 Performance to stack on an additional jab. Re-roll on this table.
6	Accurate: Your insult is provably true and very accurate. When slinging this insult, you and your allies may add your proficiency bonus to your next perception or History check. Deal 2d6 psychic damage.
7	Shameful: You make a well thought out jab that reveals a shameful activity your opponent has committed. When hurling this insult, your opponent gains disadvantage on their next two rolls. Deal 2d6 + charisma psychic damage.
8	Humiliating: You think of something that humbles and humiliates the opponent, this is so effective it can even make a dragon cry (assuming it isn't already)! You may cast the Vicious Mockery cantrip. Deal 2d8 damage.

Stout Defender

Although it may be satisfying to let out volley after volley of insults, there comes a time where you are the one who must endure the attacks. Comebacks are different than insults however. Typically they play on a hypocrisy, an insult that crosses the line, an insult that was phrased poorly, etc.

1d4	Array of Comebacks
1	Nothing: You couldn't think of anything.
2	Hypocritical: You point out that the insult was weak and/or something the insulter does as well. When using this comeback, you take half damage instead.
3	Barriers: Your comeback shows that the insulter went too far and crossed a line, as such, they gain disadvantage on their next roll.
4	Stupid: You point out that the opponent's insult was dumb for whatever reason. The effect of the insult still pertains, but you Deal 2d4 + wisdom psychic damage.

Level 6 Your word holds so much meaning and influence that reality itself seems to bend with it, you gain the cantrips Bardcraft and Druidcraft.

At level 14, you become even more skilled at manipulating the world around you with you descriptive imagery and mystical oratory. Gain the cantrips Thaumaturgy and Presdigitation.

Level 10 After practicing the weight of your word you learn to use it in the heat of combat.

When in a roast, you can take a bonus action to try one of the following:

• Intimidation: If you successfully roll intimidation, you can scare/harass the opponent to simply back down and give up. To do so, they must make a DC 8 + your Strength and Charisma modifiers wisdom saving throw. This only works on creatures with 80 or less HP.

• Persuasion: If you successfully roll persuasion, you can get into your opponent's mind and mess with their thoughts. If done, they will get disadvantage on their next two skill checks/saving throws. To do so, they must make a DC 10 + your Strength and Charisma modifiers wisdom saving throw.

• Perception: If you successfully roll perception, you can tell their mental status and fortitude just by their voice alone. This shows you their remaining HP.

Level 14 You are a man of your word, and as such other people must uphold theirs as well. While you are wearing your dapper hat, any and all promises made must be upheld. Promises that are made with you while your dapper hat is on must be upheld even when it is taken off. If the promise is broken, the breaker must take half their health in damage and gain one level of exhaustion. This cannot be enough damage to kill someone, and will simply leave them at 1HP if they are below half. This includes you.

Level 18 Your word is truly at its peak of influence. Once long rest, you can verbally assault someone. Whenever someone is verbally assaulted they take 1d4 psychic damage each time they receive an insult or magical attack.

Multiclassing

Multiclassing with the Gentlemen is Prohibited. Being a Gentlemen is a full life's work and must be seen to its end.

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