Funny / Trapped in a Dating Sim: The World of Otome Games is Tough for Mobs

Warning: Spoilers Off applies to this page. Proceed at your own risk.

General

• Every time Leon gets "rewarded" with a promotion, often leading to melodramatic tears. It gets more hilarious when King Roland who happens to be similar to Leon uses the promotions as a way to blackmail and get revenge at Leon.
• Luxion, the sassy Robot Buddy who never misses a chance to be a Servile Snarker to Leon
• Marie's Perpetual Poverty and her attempts to get out of it but unfortunately the Five Idiots making things worse than ever.

Volume 1

• Leon's Sanity Slippage after reaching his Rage Breaking Point at the Nintendo Hard "otome"/strategy game.
  • The dub version of the anime has this amazing line when pre-reincarnation Leon is forced to buy premium cheat items to get through the otome game's Fake Difficulty:
    Leon: HAHA! Behold, the Power of a FUNCTIONAL ADULT!
• In the manga, Leon despairs at having to court a noble-ranked Royal Brat like Zola due to his promotion to Baron. Balcus tries to reassure him that noble girls aren't all that bad, only for Jenna and Finley to barge in and demand more money from him. Balcus concedes the point.
• Lucas the teacher who teaches etiquette to the boys successfully convincing Leon on the virtue of the tea ceremony where before he was dismissive of it. His friends Daniel and Raymond are dumbfounded by the shift.
• The five-on-one Mini-Mecha duel of the Five Losers versus Leon is just absolutely full of both this trope and Awesome trope category.
  Leon: I'm sure Marie still has a shoulder for you to cry on, you can brag to her about your "hard work."
  Chris: (dejectedly whimpers)
  (Beat)
  Luxion: You've earned a new title: "Scumbag"
  Leon: Shut up.
  • In the English version of the manga, Leon says the following after defeating Chris:
    Leon: Save that self-pity for your girlfriend. She'll play you The World's Smallest Violin.
  • Julius tries to gain the moral high ground but instead falls into a Rhetorical Question Blunder:
    Julius: How does it feel to abuse your power and look down on others?
    Leon: ABSOLUTELY AMAZING! It's the best feeling in the world to crush you guys after you were talking so big! I may be arrogant, but you still can't defeat me. How do ''you'' feel about being beaten by someone you looked down on, Your Royal Highness?
• "Everyone, GAMBLE RESPONSIBLY!!"
  • In the Dub: Well folks, them's the harsh realities of gamblin'!
• Zola's "Oh, Crap!" Smile when she realizes she just insulted the daughter of House Redgrave.
• Jenna being punished for nearly killing her brother by... having to pull up weeds.
  Jenna: Waaah!! I don't wanna work!!!

Volume 2

• Leon's gleeful retaliation against the Offrey girl and her Exclusive Servants after they trashed his School Festival café and unknowingly threatened the queen, giving him the perfect excuse.
  Leon: I. BRING. JUSTICE!
  • ...which ends abruptly with Leon being scolded by his Tea Master.
• Leon getting distracted by Mylene's beauty while she's lecturing him about his behavior in the arena.
• Leon proposing to the queen. And getting Punched Across the Room for it by Julius. The anime even plays wedding bells when Leon proposes.
  Leon: In my previous life, I would've told this mature goddess to do it herself, BUT, I'm a refined man.
  • Even better is Mylene getting flustered and not seriously rejecting him, only making excuses such as being too old.
  • Leon justifying his proposal:
    "She's not a virgin" you say? Well most girls at school aren't virgins anyway.
    "She already has kids" you say? Hey, proof that she's fertile! Nobles need heirs so that's good trait!
    "What about her age?" you say? Who cares! I'll take a graceful older lady over a teenage Spoiled Brat any day!
  • Leon's whiny kid voice in the dub when Julius tells him to get away from his mother, like he's being told to put back a candy bar:
    Leon: Aw maaaaan, I don't wannaaaa!
• Leon's Evil Gloating as he's making a mint from gambling on airbike races.
• Leon gushing over Olivia scolding him like a naughty puppy.
• Julius and Jilk attempt to sneak out of the palace and reunite with Marie through disguises... by charging the bill directly to the kingdom's payroll, which lands the request form right on Queen Mylene's desk. She questions out loud how they could possibly be this stupid and throws the request straight into the trash. And they're still surprised to learn it was rejected.
• Leon trying to bribe a charms vendor for his entire stock of Status Buff charms and escalating his offers until Angie yanks him by the ears (unfortunately cut from the anime).
• Leon donating a pile of cash to the shrine and praying out loud for a good marriage with a woman who's mature, well-endowed and perverted, causing Angie and Olivia to drag him away by each ear.
  • Not long after, he gets what he prayed for when he meets Deirdre—she's older than him, has the curves, and wants to make him her pet, though that last part creeps him out.
  • In the LN side story, Leon goes even further and outright wishes for the queen. After which Livia and Angie finally drag him away from the temple.
  • In the manga, Leon's wish was so perverted that the young shrine maidens were furiously blushing, making the Ear Ache scene funnier.
• During a tense exchange, Livia quickly rattles through each of the Five Idiots' major flaws when Leon asks why she wants him and not them:
  Leon: There are better guys! Like Prince Julius...
  Livia: I hate him! He abandoned Angie!
  Leon: What about Jilk?
  Livia: He's a rotten schemer!
  Leon: Brad?
  Livia: Narcissist!
  Leon: Greg?
  Livia: Meathead!
  Leon: Chris?
  Livia: Needy!
  Leon: Huh, you've got 'em all pegged. This is actually amusing.
• And after they reconcile, Livia hugs Leon from behind as he steers back to the Partner. Leon awkwardly thinks he'll feel certain things, except...
  Luxion: I designed Master's suit to withstand all external pressure.

Volume 3

• When Hertrude tries to seduce Leon by claiming that he was leering at her, Leon takes a quick look at Angie and Olivia, compares them to Hertrude and Marie, then sincerely apologizes. Hertrude's reaction is comedy gold:
  Hertrude: W, why are you looking at me with pity now? What are you doing that for?
• The entire "power of friendship" scene:
  They resigned themselves—I mean, steeled themselves for the upcoming challenge. Either way, they agreed to follow me.
  See Principality? It's The Power of Friendship!
• The Love Meter scene features mostly one-sided Relationship Values, such as Roland and Mylene having a depressing score of 25/58. Marie's relationships with the dateable five are much worse, as she had pathetically low scores for all of them. At least they take it in stride, much to her embarrassment. Finally, Olivia and Angelica turn out to have a perfect score of 120/120, and this is after they and everyone else tried to force Leon onto the machine.

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