Naruto: The Outsider's Resolve - Chapter 2.0 (051):

In the beginning, when they all thought that she was “he”….

ML #1: We will be brothers for life!

ML #2: This time I’ll reluctantly let you have the #1 seat.

ML #3: I will properly repay royal teacher!

ML #4: Ah Rong is my closest little brother, I trust him.

Afterwards…

MLs: I’m seriously such a fool.

MLs: What do I do, I think I’m gay. I fell in love with my bro/rival/teacher….

Afterwards….

MLs: I’m straight! As straight as steel!

Note:
MC is a girl crossdressing as a boy, she knows how to fight, and naturally possess the gold finger halo from the author.

All the ML(s) is the same person, 1v1, sc, HE

- Description from Novelupdates

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In a usurped kingdom , amid a war-torn and blood-soaked Italy, Conradin's battleground is set. To reclaim his birthright the crown of Sicily, he must tread a path paved with blood, learning that he must do whatever it takes to ascend the throne.

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In the year 1266, the tale of Conradin, the last scion of an ancient imperial dynasty, unfolds. His once-great kingdom, Sicily, has been ruthlessly usurped first by his own uncle and now rests in the hands of the cunning French Count Charles. Through a treacherous plot involving the Pope, Charles managed to oust the Hohenstaufen from the Kingdom of Sicily and crowned himself as its king.

In the East, powers such as the Despotate of Epirus are keenly observing the instability in Sicily, poised to seize any advantage that may arise from the chaos. Meanwhile, the small Italian communes are caught in the political crossfire, aligning themselves with one side of the conflict or the other based on the prevailing political party in power and their vested interests. These shifting allegiances turn the Italian peninsula into a powder keg, where all-out war seems inevitable.

As the shadows of history close in around Conradin, the world watches with bated breath. Will he emerge triumphant, his name forever etched in the annals of Sicilian glory as the rightful king who defied insurmountable odds, toppling both the Pope and the usurper? Or will he, in his valiant struggle, become a tragic figure, a symbol of lost opportunities and shattered dreams? The future of Sicily hangs in the balance, and Conradin's destiny remains uncertain, poised on the precipice of history.

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If life could repeat itself, what would you do?Would you repeat your first life and stay a normal average joe? Perhaps your gaze will betray the life you’ve already lived, but you remain insignificant and unknown, stretching your neck up high to watch the furling clouds roll by?Or will you make the world your stage, stir up every cloud and wind under all the heavens, making the entire world your captive audience as you dance, making people’s hearts pound with your every move?Composing my own laws, establishing the order I desire…a human life is a measly ten decades, so why don’t I light the candle that is my life and set this world ablaze!!

Lin Wan regrets her inability to judge people and how she was deceived by a friend, eventually discarded by a worthless man, leading to her ruin and disgrace. She was forced to leave behind a vibrant and courageous person, ending up living a miserable life and facing a bleak old age.Reborn into another life, Lin Wan is determined not to repeat past mistakes. She is set on extinguishing her vain desires and living a truly remarkable life. She has many ambitions.But the most crucial one is: to win back the man who truly loves her once again. She plans to earn money, find him, marry him, and live a happy life together!