[Extended Summary]: It's been fifteen long years since Regina Mills signed those adoption papers. Never once did any curse, magic or fairytales exist within Storybrooke. While Henry never found his birth mother, Regina has trouble getting through to her son. Without Emma's return for Henry, the pair's estranged mother and son relationship shared in Season 1 only spirals out of control. Regina, who's heart was broken by her own mother, is now so incapable of expressing love in a normal way understood by her son, who like Regina, only ends having his heartbroken by the one person who loves him more than he shall ever know.

Mom,

By the time you've read this letter, I'll be gone. Wherever I'll be going is none of your concern. Regardless of wherever I decide to stay, I believe I'll survive perfectly alright on my own.

During the time you've spent hurting others, I've spent time researching about the outside world, just past the white boarder line on the main road. A world where people are given the kind of freedom I know I'll never be able to have here in this small town. You spent so much time fixated on the idea of turning the dreams of others into dust, you never properly understood what I truly needed from you as a mother.

As my mother, you were supposed to love me— your only son, unconditionally. Yet, I felt as if you never loved me enough. In your mind, work always came first, while staying home to study was supposed to be my top priority. You always believed that the children next door, who where once my friends, threatened your wellbeing and so, for years, you forbade me from playing with them next door, manipulating me into believing that any physical contact with them would only further corrupt my already bright and optimistic mind.

In your absence, Miss Blanchard was the only one who supported me enough for me to see the best in you. If it wasn't for her, I would have disappeared long before my emotions were destroyed beyond repair; but knowingly as my mother, it was no secret that you couldn't stand Miss Blanchard and her preachings of hope and love, so you threw my only book of fairytales, my sole symbol of hope, into the fireplace—setting it aflame, while I watched it turn into nothing but the ashes of what it once was before.

All these years, the only thing you have truly cared was how you could raise me to become your "perfect" son, but Mother, have you truly ever considered my happiness in the process? Have you ever considered how doing all of this would inevitably push me farther away from you instead of bringing us both closer together? The way you pushed me so forcefully to compete with everyone else only left me hating you more and more every sunrise and sunset; but most importantly, you never realised that the true reality I deserved was in fact my own imagination and never the case vice versa.

I spent many nights struggling to fall asleep alone, staring at the flickering green stars that decorated my otherwise plain white ceiling; wondering why my mother would hardly ever lie next to me on my duvet and count the thousand true stars that gleamed so brightly in the night sky, just outside my bedroom window. I struggled to understand why you never really bother to ask me how my day went, or inquire I was feeling, as any other mother would.

The sad truth is Mother, I don't think you ever understood how difficult it was to see my the other children so loved by their parents, while I never received that same treatment from you. I tried so hard to impress you, but all I seemed to do was make you more and more disappointed. Either way, no matter what I ended up doing, I was never good enough for you to flaunt to those who blessed you with their presence.

While you spent many hours at work, I spent all my neglected afternoons at the library with the broken clock tower you were never bothered to fix. I studied maps and read through stories that were written long before my time; and, for the first time in a very long time, I learnt something valuable: how to believe in the impossible, no matter how impossible it may seem. What I had managed to discover in the dusty old library will always remain a secret but I can assure you, whatever it was, it was powerful enough to finally show me the truth I had deserved.

Madam Mayor, I am not you son; I never truly was and never will be. No matter how many times you claim to loved me, say you want fix me and or promise to change me, I will always remain true to myself and begin my journey towards my true destiny.

It is not written in the stars for me to be with you mother, and I shall respect that fate enough to make my own decisions this point on in my life.

With this change, I'll shall finally be able to have a life free from your confining grasp, free to breathe the air I want to breathe and to befriend the people I want to trust. Your motherly love never nurtured the love and respect I once held so highly for you, only feeding into the growing hatred inside my heart that was once so pure. After all, when it comes down to this, you never tried to understand me like a real mother would have truly understood their own son.

You never gave me my best chance…but I have decided that I shall give you yours. I owe that to you, as your only child and your only son, I believe I at least owe you your best chance.

I've taken everything that belongs to me and returned everything that belongs to you. Anything you have ever kindly provided me with in the last fifteen years of my life has been neatly kept and stored inside the oak wardrobe in Nana's old bedroom.

I promise you shall never hear from me again.

The outside world hardly has any rules that confine the best selves of the people living within it, and I know I will have a life greater than anything once I've left Storybrooke. After I cross the border line on the main road, there is no turning back; I won't be able to remember who you are anymore and I believe, I won't regret it the choice I am about to make.

Goodbye, Madam Mayor and I wish you all the best in life. I truly hope a life without me will give you your best chance and allow you to become the person you truly wanted to become all those years ago, before I interrupted the momentum your life.

Your son,

Henry.

A/N: I'm fairly new to Once Upon A Time and wanted to awhile for longer before I wrote a proper one-shot for any character/relationship, but then I watched Henry and Emma talk about family in Henry's castle in Season One and then my heart SHATTERED, and I mean SHATTERED into a million pieces,,,

and when I knew how willing Regina would be to die for her son who, at that point was so unbelievably unaware about her love for him, I couldn't help wonder what if they (Regina and Henry) never worked out their relationship in the rest of the seasons and BAM this little one short was born!

I hoped you enjoyed this one-shot; I hope I managed to capture AU motherly Regina in the best way possible (also shout out to the hours spent on the OUAT Wiki trying to solve the family tree, RIP that was way more complex than any Harry Potter pureblood family tree to ever exist). I'm trying to write as much as possible but my final year exams are so soon (3 months to go) so after that I'll be free!

P.S: Both CaptainSwan and SwanQueen and are ENDGAME,,,I will always be trash for both ++ Robin.