Dylan has been a Jester all his life and after being kicked out of the Hero's party, he decided it was time to change his job to Sage. Having been forced into a supporting role and labeled an incurable playboy thanks to side effects of his job, he intends to step out into the spotlight with his new power and become a Hero in his own right. Joined by two super short and super busty girls, Tina the warrior and Nyannyan the thief, what direction will his brand new adventure take?
Did You Know That a Playboy Can Change His Job to a Sage? is a Web Novel by Shippo Senoo. It has a manga adaptation.
- Accidental Pervert: The jester's 'Lucky Perv' skill is designed to invoke this. Dylan's job as a jester also causes him to put on shows for people...and to flirt with almost every woman he sees. This combination of traits leads people to assume he's a pervert when he's in fact a real gentleman.
- Advancing Boss of Doom: The Stalker, the strongest monster on the 10th floor, will relentlessly pursue adventurers until they reach the 1st floor.
- Alas, Poor Villain: The ultimate fates of Aiza and Mills. The former is sold as a slave to the Church of Monte by her own family while the latter is betrayed by her own church and both are targeted for assassination using an insane serial killer who targets adventurers for fun. Despite how karmic their fates may have been, the manner in which they happen subverts all catharsis that might have been obtained.
- The Atoner: When Laius turns back up to help Dylan's party fight the headhunter, he is not only one himself, but is apparently part of an entire party of people atoning for past crimes.
- Born Lucky: Tina has an EX-rank Luck stat, which is implied to be strong enough that it caused the dungeon to hide its own stairs up just because she wanted to spend more time with Dylan, only to immediately reveal those same stairs when Dylan mentions that higher floors could help her afford armor that fits her immense bosom.
- Bunny-Ears Lawyer: While Dylan maybe the "Jester", he's honestly more accomplished (level 99) compared to his former less-than-stellar teammates (level 35). Even with his level reset from his job change into a Sage, his stats mostly remained the same.
- Complaining About Rescues They Don't Like: The hero's party got in way over their heads to the point that Dylan was forced to use their emergency teleportation crystal to escape the Demon continent and prevent a Total Party Kill. They could only complain at the loss of fame, glory, and the dreams that would come with it and kicked him out.
- D-Cup Distress: Tina did not have an easy time back home because of her early and rather extreme blooming. Her chest made it awkward for her to do anything without people being uncomfortable around her, despite her class working best with full body armour her figure means she can't get armour that will fit her, and her chest is so large that it dictates a lot of her movement. Dylan has to train her Wax On, Wax Off style to help her with her sense of balance.
- Deconstructed Trope: Tina's boobs are treated as more than just Fanservice or Comic Relief (though they get their fair share of those too) and she has had genuine problems being an adventurer with them, from having trouble with her balance to being unable to find decent armor that fits.
- Does Not Know His Own Strength: Downplayed, but also realistic. Warrior skills are mighty, but are absolute hell on weapons not forged with such strength in mind.
- Eating the Eye Candy: Dylan is very much inured to the sight of attractive ladies by this point, and can remain focused no matter how well endowed or underdressed they might be, but Tina turns into a blushing mess from just a glimpse of Dylan's abs.
- Entitled Bitch: Aiza fit this to a T even before the group disbanded, and more so than Laius (who at least had a Heel Realization offscreen). Even after having lost everything and being forced to become completely subservient to Mills, she still makes demands of Dylan while belittling him, and has the audacity to be offended when he responds by telling her exactly where to shove it.
- Even the Guys Want Him: Often when Dylan's party saves another group that has both male and female adventurers, Dylan will reflexively flirt and everyone in the saved party will blush.
- Evil Counterpart: The headhunter proves to be this to Dylan. Both have advanced classes, access to powerful abilities, and have a host of tricky abilities to confound enemies. However, where Dylan loves to make people smile, is undeniably heroic, and adores the spotlight, the headhunter loves to torture and kill others for fun, can't stand heroic people, and works from the shadows.
- The Face: Dylan took care of all social interaction for the highly dysfunctional heroes’ party. So much so that when he was kicked out, the remaining members became outcasts on the run from the law within days.
- Fantastic Nuke: Dylan uses one to destroy a seemingly endless army of skeletons.
- Fighter, Mage, Thief: Appropriate for a series that references an Easter Egg from the Trope Namer, Dylan’s party consists of this with Tina in the Fighter role, Dylan himself in the Mage role, and Nyannyan in the Thief role.
- The Fundamentalist: When Dylan confronts Mills with idea that the Monte Faith, her faith, is a Corrupt Church, she immediately marks Dylan as a heretic who must die, dropping any pretense of making peace with him.
- Glory Seeker: The members of Dylan's former party were more interested in personal glory for various reasons: Laius the Swordsman was a Narcissist, Mills the Priestess was a Fundamentalist and Aiza the Mage was an ambitious Social Climber despite already being of noble birth. The only thing that united them was their utter contempt of Dylan the Jester, despite the fact that he was the one who kept the party going by doing all the mundane tasks that the others considered beneath them such as carrying adventuring gear, purchasing supplies and negotiating with people.
- Hates Being Touched: Aiza has this to psychotic levels.
- Heart Is an Awesome Power: Unlike Dylan's moronic party who thinks otherwise, Dylan's abilities puts him in a better chance against the Demon Lord. Not to mention, he pretty much did the heavy lifting throughout their adventures such as being the charismatic face of the party when it came to talking with people and providing potent buffs.
- Heel Realization: After finding himself broke and hated, Laius eventually realizes that dismissing Dylan from his party was a terrible mistake. At first, he offers to take Dylan back but, with some persuasion from Dylan, decides instead to start over again as a hero.
- Hero Killer: The rumored Headhunter who likes to murder adventurers and take their heads for fun. When he is introduced after killing Aiza and Mills, he taunts Dylan by showing him the heads of two parties that his group had previously saved.
- Holier Than Thou: Mills genuinely has no respect for anyone or anything not part of her religion and actively looks down on them, only playing at being humble when the situation is very clearly not in her favor.
- Humiliation Conga: After kicking Dylan out, the remaining members of the hero party did not have a good time. For starters, they had to hide their identities, take mercenary work to try and earn enough money to get back to the demon continent, had their luggage stolen, got kicked out of the inn they were staying at, and were split up when the guards were called on them.
- Hypercompetent Sidekick: Dylan to the rest of the heroes’ party. Leaving out his critical duties as The Face; Laius, Aiza, and Mills all had levels in the mid-30s while Dylan was level 99 before joining.
- Inept Mage: Implied with Aiza. Though she was still heavily outmatched by Dylan, the fact that she was convinced that Fireball was the strongest spell despite the latter saying otherwise, and who overpowered her easily with a Firelight spell was enough to trigger a Villainous Breakdown.
- Loved by All: Dylan's kingdom really revere him.
- Love Triangle: In chapter 18.5 of the manga, Dylan sleeps with both Tina and Nyannyan, with Nyannyan letting Tina go first before joining in because she can see how much Tina loves Dylan.
- Luckily, My Shield Will Protect Me: Since Tina’s chest prevents her from getting quality armor, she uses an oversized shield as her main means of defense.
- Magikarp Power: The entire premise of the plot focuses on the fact that useless Jesters can become almighty Sages at high levels.
- The Main Characters Do Everything: Dylan had to cover most of the holes his former party left in their questing strategy by his lonesome. Thus since he was doing most of the work himself he ended up gaining the most experience and leveling up far more than any of them.
- Never My Fault: Dylan's former party certainly think they are devoid of blame, particularly Aiza. Only Laius eventually manages to accept responsibility for his own mistakes.
- Old Friend: Dylan and the Resplendent Lords, his old party before joining the 'Hero', whenever they happen to be in the same room together. There was apparently a falling-out between them long ago, but you wouldn't guess it from how they treat each other.
- Older Than They Look: Tina and Nyannyan are both grown eighteen, yet aside from their chests Dylan thinks they don't look older than thirteen. This is mostly due to how short they are.
- One Head Taller: Exaggerated a bit. Tina and Nyannyan are both super short at 4’6”. The top of their heads only come up to the lower part of Dylan’s chest at best and when he gets on one knee he can still look them in the eyes.
- Only Sane Man: Practically anyone that's not selfish royalty nor Dylan's former team.
- Really Gets Around: Downplayed. While Dylan's job as a jester compels him to flirt with nearly any pretty girl he sees, and arranges Accidental Pervert situations, he doesn't actively pursue every woman he flirts with. That said, when he first wakes up with a naked Tina and Nyannyan after sleeping with both of them, he reflects that this isn't the first time he's woken up in bed with two naked women.
- Red Baron: The entire heroes’ party gets these. Laius the Warrior is “Conquering Sword Hero”, Aiza the Wizard is “Mage Hero”, Mills the Priest is “Saint Hero”, and Dylan with his flirty Jester support class is merely “Playboy”. Deconstructed in that the three ‘Hero’ titles were granted by the alliance of kingdoms as incentive to join the campaign against the Demon King rather than as recognition of deeds already accomplished, and Dylan is the most accomplished of the group by a wide margin.
- Refusal of the Call: According to the light novel, the main reason why the members of the hero’s party were so low level was because all the high-level adventurers (save Dylan) turned the offer down on the mistaken assumption that they’d only be fighting low-level monsters.
- She's Not My Girlfriend: Notorious playboy Dylan turns up again one day in the company of a cute girl with an extremely generous figure in less than ideal clothing for her class? Naturally, everyone's minds turn to the obvious even after he corrects them.
- Stage Magician: The jester job is basically this, but with actual magic in their tricks.
- Supporting Protagonist: Dylan did all the grunt work that his former party thought was beneath them, yet was vital for them to continue on.
- Support Party Member: Dylan’s former Jester class. It has a lot of showy and flashy techniques designed to distract and mesmerize opponents, but just about zip in the way of pure offensive ability. He keeps these techniques after upgrading to the Sage class, which has offensive power to spare.
- Tall, Dark, and Handsome: Dylan would be a perfect walking stereotype of this trope if he dressed in darker clothes.
- Throw the Dog a Bone: In-Universe, after Laius begs Dylan to return to the hero's party and is turned down, he finds that Dylan slipped enough money for some meals, a referral letter to the guild, and a magical transfer passport into his pocket so he might be able to start over as an adventurer. All because Laius was the only one to apologize for his treatment of Dylan in any way.
- Too Dumb to Live: When mistaken for a prostitute at an inn and getting her breast fondled, Aiza flies into a blind rage and destroys the entire inn along with everyone inside with an explosion spell. When guards arrive at the inn's ruins to arrest her, Aiza continues hurling destructive magic at them until she is subdued. When brought before King Theoderic, she tries to lie and blame others for her misery despite there being many witnesses to her crimes, angering the king even further. In the end, Aiza finds herself having to turn to the Monte Faith for her freedom, effectively becoming Mills' slave.
- Ultimate Blacksmith: Aminasmiths of the beast tribe (Nyannyan is one) whose works are known as 'Dragon Killers'. Their works are so valuable that most animasmiths prefer to hide their identities so as not to be swamped with requests or targeted by greedy people.
- Victoria's Secret Compartment: Tina keeps her adventurer's card in her ample cleavage.
- Whole-Plot Reference: After a fashion — the basic conceit of the novel is sourced from the old Easter Egg in Dragon Quest III, wherein a sufficiently leveled Jester/Goof-Off can class change into Sage (the strongest caster class) without the need for a specific item the way other classes do. Even Dylan's old party is built the way a player might angle for a late-game caster-heavy party in that game (e.g. Laius is the Hero, Mills is a Priestess/Cleric, Aiza is the Mage, and Dylan is the Jester you drag through the early game until they can class change, at which point the party really "comes online"). The entire point of the novel is to tell a story like that from the perspective of the Jester at the point they aren't useless anymore.
- Wrecked Weapon: Something happened with the hero's party before Dylan was kicked out that caused the Holy Sword to be broken. Also a general problem Warriors can have if they use substandard weapons with their skills.
