MTL - I Became the Favorite of Big Bosses - Chapter 498 belated encounter

That afternoon, Roland received the most absurd gift imaginable—his stepmom handed him a System literally.That’s right. Not a game console. Not money. A real, cheat-like System... the kind usually reserved for transmigrators and chosen ones.Except Roland had transmigrated eighteen years ago, and nothing remotely “chosen” had ever happened since—until now.The catch? It wasn’t just any System. It was the “Mother's Little Tasks” System, formerly owned by his doting (mysterious) mother. And its first mission?[Mission: Go on a blind date.][Target Options: Yukino Yukio (Mom), Yukino Haruno (Elder Sister), Yukino Yuki (Younger Sister).][Warning: Once locked, your chosen girl can never marry anyone else.][Reward: 1000 Points, one self-selected supernatural ability from Mall]Roland: “...What kind of twisted matchmaking app did I just inherit?”After reading the mission, Roland was stunned. An arranged romance at 18 was already bad—but a binding rule that prevented the chosen girl from marrying anyone else? What if he failed the mission? Would she be alone forever?“And this is supposed to be a System?”“Mom! What the hell is this mission?” Roland asked, his face darkening.“It finally triggered! All those Points I spent transferring the System weren’t wasted,” his mother replied cheerfully, ignoring his outrage.“You set this up? Why?”“You’re nearly an adult and you’ve never even dated. Of course I’m worried.”“I’m only eighteen! I have college entrance exams next year!”“Exams don’t matter. But youth without love isn’t youth at all.”“...Is that something a mother should say?” Roland muttered. Most mothers pushed their kids to study harder—his acted like grades were irrelevant.“What kind of mom does this to her own son? And why is Aunt Yukio even on the target list? That’s just insane!”“Well~, I don’t know what kind of girl you like. The Yukino family has all three types—mother, elder sister, and younger sister—so I gave you options.”

The scum’s or villain’s long road of transformation was tentatively set to the world:
The abandonment of the educated youth’s wife (Completed)
The hidden marriage of the scum film emperor (Completed)
The best brother in the world (Completed)
The Phoenix male who destroy the bridge after crossing the river (Completed)
The treasonous general (Completed)
I’m an honest man (Completed)
To become the top scorer in the School of Agriculture (Completed)
The soft rice man’s self-cultivation (Completed)
The whole world is reborn (Completed)
I want to survive on a desert island (Completed)
The stallion male who has seized the opportunity (Completed)
The perverted self-salvation (Completed)
The spring of the loafer (Completed)
The misplaced life (Completed)
The miser career (Completed)
The ghost is out of feeling (Completed)
The Queen’s favorite husband (Completed)
The vicious girl with her godfather (Completed)
I want to be a good person (Completed)
I does not tear up the family (Completed)
The perverted common plant (Completed)
The Mary Sue’s men (Completed)
Every time I was reborn, someone wants to kill me (Completed)
The old people’s counterattack path (Completed)
The global evolution (Completed)
When I became a net red (Completed)
For you, good person (Completed)
His heart had white moonlight (Completed)

- Description from Novelupdates

Rhodes accidentally tripped and fell while playing with his phone as he walked down the stairs, only to find himself transported to the world of Fairy Tail.To his surprise, he discovered that he had the ability to summon various wild monsters from League of Legends and even learned how to use Receive Magic.But that wasn’t the main issue. The real problem was that, among a guild full of reckless individuals, there was suddenly someone who actually liked making plans.Some people believed he was destined to become the next guild master.But Rhodes knew the truth—becoming the guild master of Fairy Tail meant endless self-reflections and a never-ending pile of compensation bills.Determined, Rhodes made up his mind: I don’t want to be the guild master!

Gu Chaoyan is the eldest daughter of the Gu Family, yet the least favorite one. She is mostly despised and belittled by everyone around, only because she isn’t pretty.