1 - 20 of 140 Works in Harry Castillo

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  1. Tags
    Summary

    after lucy, harry believed he was destined to be alone. he had given up on his dream to be a father and husband. that is, until he met you who gave him hope for a future he thought was lost.

    Series
    Language:
    English
    Words:
    112,052
    Chapters:
    22/?
    Comments:
    193
    Kudos:
    152
    Bookmarks:
    37
    Hits:
    7,646
  2. Tags
    Summary

    Between the stress of wedding planning and his own pride, Harry is at his wit's end with Elizabeth, the new maid who refuses to back down. Their constant collisions culminate in a kitchen argument so intense it blurs the line between animosity and attraction. Prompted by a dare from the head cook, the two trade lives for a night. As Harry faces the warmth of Elizabeth's cozy home for dinner and Elizabeth enters the glamour of the gala, they’re forced to see if their assumptions about one another and themselves, hold any water.

    Language:
    English
    Words:
    33,163
    Chapters:
    5/?
    Comments:
    2
    Kudos:
    4
    Bookmarks:
    1
    Hits:
    91
  3. Tags
    Summary

    https://buymeacoffee.com/brookeswords

    Pairings: harry castillo x fem!reader

    Content warning: fluff, explicit smut, strangers to friends, friends to lovers, rom-com, adult language, double life. If you are a minor don’t read it.

    A booking mistake and a brutal snowstorm trap you in a remote cabin in Iceland with a stranger. You never expected to meet someone as perfect as him and he never expected to meet someone like you, someone unlike anyone in his world. Snowed in together, you both tumble into something warmer and deeper than either of you imagined, falling for each other harder than the snow outside.

    But once you step out of the Icelandic snow globe and into the reality of the big city, one question remains:
    Can the double life Harry built to protect you survive the truth?

    With you, Harry will learn that real love never comes with a price tag.

    Language:
    English
    Words:
    24,518
    Chapters:
    6/?
    Comments:
    1
    Kudos:
    14
    Bookmarks:
    2
    Hits:
    354
  4. Tags
    Summary

    All of the PP boys One-Shots, enjoy.

    IMPORTANT NOTE ABOUT THE PP ones: This is FICTIONAL work, I mean no disrespect or objetification of PP, I'm writting about a fictional version of him. Just to make it clear!

    Language:
    English
    Words:
    88,053
    Chapters:
    28/?
    Comments:
    8
    Kudos:
    25
    Bookmarks:
    2
    Hits:
    1,556
  5. Tags
    Summary

    Harry Castillo and you have been married for a while and are trying to get pregnant, but the tests keep coming back negative. So you have to keep trying, which you both don't mind. Like, at all.

    This story was inspired by a tweet by @P4SCALexe. Thank you for the idea!

    Language:
    English
    Words:
    4,942
    Chapters:
    2/?
    Comments:
    2
    Kudos:
    13
    Bookmarks:
    1
    Hits:
    349
  6. Tags
    Summary

    In some families, the past doesn’t vanish—it lingers like a cigarette burn on celluloid. You came from one of those. Your grandfather’s name is still on soundstages. Your mother won awards she never picked up. You didn’t just inherit money, but myth.

    You grew up in rooms curated by people who no longer existed, in houses unchanged since the sixties. You were taught not to need. Still, you did. Spoiled, maybe—but never cruel.

    Harry Castillo’s wealth was different...newer, cleaner, all balance sheets and deal terms. His mother built their firm; his father and brother followed. He lived in a Tribeca penthouse so pristine it looked like a set waiting for actors.

    He’d just ended things with Lucy Mason, who worked at Adore Matchmaking. It was mutual, more or less. She told him to call, if he ever got lonely in the way men like him sometimes do.

    You didn’t know about any of that. You were busy with your own life. You didn’t know your sister had sent in forms to a matchmaking service with your photo and a profile listing all your icks.

    Not until they told you...there was a match.

    And his name was Harry.

    Language:
    English
    Words:
    61,083
    Chapters:
    5/12
    Comments:
    36
    Kudos:
    199
    Bookmarks:
    45
    Hits:
    4,009
  7. Tags
    Summary

    Harry Castillo has spent years building a life in the city where everything has a price—except honesty. When his mother’s memory begins to fade, he returns home and hides the truth about who he is for the sake of being seen—craving something ordinary, something real. When he finds himself at a familiar diner he used to visit as a kid, he meets you—a single mother with a son who carries a thousand quiet burdens, and a resilience he can’t look away from.

    But what starts as quiet companionship over cheeseburgers and milkshakes turns into something deeper—Harry faces a choice: reveal the truth and risk losing the only person who sees him for who he truly is—or keep hiding behind the simplicity of being “just Harry.”

    Series
    Language:
    English
    Words:
    60,075
    Chapters:
    7/10
    Comments:
    34
    Kudos:
    30
    Bookmarks:
    11
    Hits:
    1,261
  8. Tags
    Summary

    Mara Barea is a freelance architect—an expert at building walls, especially around her heart. Harry Castillo is her billionaire client: controlled, cold, and far too handsome for his own good.

    She just wants to finish the job, get paid, and walk away unscathed. He shouldn’t notice the way she bites her lip when she hesitates.

    But some things aren’t designed. They’re felt—deep under the skin.

    Two worlds. One penthouse. And a tension no blueprint could ever contain.

    Language:
    English
    Words:
    51,239
    Chapters:
    43/?
    Comments:
    1
    Kudos:
    30
    Bookmarks:
    5
    Hits:
    1,669
  9. Tags
    Summary

    After your prom night falls apart, and your brother disappears with his on-again, off-again girlfriend, the only person who steps in to comfort you is his best friend, Harry Castillo.
    Somewhere between heartbreak, stolen moments, and a slow dance under the moon, you make a reckless little pact: if you turn thirty and neither of you is married, you’ll marry each other. Years later, at your brother’s wedding, you and Harry cross paths again. He’s different now. You’ve changed too. But something between you feels exactly the same, and you are not “kids” anymore.

    Language:
    English
    Words:
    52,004
    Chapters:
    12/?
    Comments:
    15
    Kudos:
    54
    Bookmarks:
    9
    Hits:
    1,352
  10. Tags
    Summary

    This drabble takes place right after Harry and you put Lucy in her place in Chapter 12. The bedroom door closes—and the tension doesn’t disappear. It combusts.

    Series
    Language:
    English
    Words:
    3,190
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    12
    Hits:
    243
  11. Tags
    Summary

    Your wedding was cancelled.
    Your fiancé ran off with your friend.
    Your honeymoon to Iceland is non-refundable.

    So you go anyway. Alone.

    And you don’t expect to meet anyone, least of all the man who could quietly rearrange your entire life.

    *Each chapter will include their own content warning*

    Language:
    English
    Words:
    17,088
    Chapters:
    6/?
    Comments:
    8
    Kudos:
    30
    Bookmarks:
    4
    Hits:
    569
  12. Tags
    Summary

    you don’t believe in love, you just write about it convincingly enough to get paid for it. You agreed to go on these blind dates instead of your heartbroken friend and for the column content and free dinners, never expecting anyone to see through it. But then Harry does, and instead of walking away, he makes you another deal.

    Don't steal, translate or feed this work into AI please, respect the writers!

    Language:
    English
    Words:
    163,688
    Chapters:
    10/17
    Comments:
    12
    Kudos:
    53
    Bookmarks:
    9
    Hits:
    1,704
  13. Tags
    Summary

    Ex Husband!Harry castillo x F!Reader
    Born and raised on the Upper East Side — mother’s an actress, stepfather runs an empire that’s suddenly “under review,” and your brother’s the reason you have gray hair. You married perfection in your 20s Years after your picture-perfect marriage went up in smoke, you left New York to “heal.” Now you’re back, in your 30s — and saw your ex-husband on the cover of TIME. Wow.
    He got richer, your family’s going down, and somehow, you ended up working for him. Cried? Yes. Bad idea? Definitely.
    What could possibly go wrong?

    Series
    Language:
    English
    Words:
    162,884
    Chapters:
    12/?
    Comments:
    125
    Kudos:
    227
    Bookmarks:
    46
    Hits:
    3,295
  14. Tags
    Summary

    You've been Harry Castillo's personal assistant for five years - making sure everything runs smoothly in his life. You've been there for it all - good and bad - particularly Harry's quest to find that special someone to love and marry. Now he thinks he might have found it in Lucy Mason - his brother's matchmaker.

    But you're not convinced. There's something about Lucy that you just can't put your finger on, but which tells you that she's not the one he should be with. But there's only so much that you can say, because you and Harry are not friends. This is a professional business relationship. Deep down, you believe you can give him everything he needs, but you can never tell him because you don't want whatever this is to end.

    Language:
    English
    Words:
    74,434
    Chapters:
    19/?
    Comments:
    286
    Kudos:
    203
    Bookmarks:
    49
    Hits:
    5,803
  15. Tags
    Summary

    you and harry visit a lingerie store.

    a drabble for then came you

    Series
    Language:
    English
    Words:
    2,814
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    18
    Hits:
    364
  16. Tags
    Summary

    Jess is a photographer in Brooklyn and meets her charming new client.

    Language:
    English
    Words:
    3,187
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    6
    Hits:
    85
  17. Tags
    Summary

    Adore was supposed to be able to find someone compatible for Harry Castillo.
    A unicorn in the dating world, as Lucy called him, it should have been a piece of cake.
    But when every woman he sees just makes him question why he even tries... Well, Lucy is forced to take drastic measures.
    Which include setting him up on a 'not-date' with her fiancé's high-school best friend.

    Cait is a (nearly) broke artist living in the outskirts of Manhattan, just trying to get by. In her eyes, the less people that notice her, the better. She just wants to make her art and live in peace with her cat, Eowen.
    But when Lucy asks her to take her ex-boyfriend out on one 'not-date'... well, maybe the paint fumes have gotten to her, because she says yes.

    Language:
    English
    Words:
    13,181
    Chapters:
    6/?
    Comments:
    6
    Kudos:
    19
    Bookmarks:
    3
    Hits:
    354
  18. Tags
    Summary

    You suck Mr. Castillo’s soul out under his office desk at his company while he is on a business call.

    Language:
    English
    Words:
    4,046
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    27
    Bookmarks:
    2
    Hits:
    588
  19. Tags
    Summary

    it's harry's birthday! he's spent the last year getting back in touch with those he cares for and rediscovering love, though his life still lacks romance. or so he thinks.

    Language:
    English
    Words:
    3,270
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    6
    Hits:
    106
  20. Tags
    Summary

    The one where Harry is left at the altar, but a trip to the beach brings him a surprise with the ocean waves.

    Series
    Language:
    English
    Words:
    11,814
    Chapters:
    3/?
    Comments:
    4
    Kudos:
    15
    Bookmarks:
    3
    Hits:
    282

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