20 Works in Matchmaker Dean Winchester

Listing Works

  1. Tags
    Summary

    When Dean suffers from his feelings for his brother and the angel Castiel, he decides to do something about it. He tries to matchmake them on a dating app. He gets the app himself, only to look if those two really get it on of course. But somehow he starts flirting with them anonymously and falls even harder for them. Is there a way out without hurting anyone?

    Language:
    English
    Words:
    10,242
    Chapters:
    1/1
    Collections:
    1
    Comments:
    8
    Kudos:
    95
    Bookmarks:
    19
    Hits:
    1724
  2. Tags
    Summary

    Snowstorms meant boring nights being the world's most useless hero wannabe. Sam kept the Beanery open and waiting in case of people trapped out in the storm, but rarely expected anything to happen. He can play on his computer and dream of being a real hero, like Farsight and Foresight, the hottest heroes in town.

    Series
    Language:
    English
    Words:
    2,191
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    20
    Bookmarks:
    3
    Hits:
    119
  3. Tags
    Summary

    Sam has an important message to get to Ben Solo. Unfortunately, nothing ever goes as planned for the Winchesters.

    Series
    Language:
    English
    Words:
    6,515
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    5
    Hits:
    83
  4. Tags
    Summary

    I've just been so sick and tired – metaphorically – of the whole covid19 debacle, that I had to write my own little fix dissing the entire thing. So, thus was born Dean being just as done, and Castiel coming up with the perfect solution of taking him away to a private island with only them and the staff, no viruses to worry about. Oh, and Sam is along for the ride, because how could he not be?

    Language:
    English
    Words:
    3,806
    Chapters:
    1/1
    Comments:
    15
    Kudos:
    104
    Bookmarks:
    10
    Hits:
    1128
  5. Tags
    Summary

    You've finally worked up the nerve to ask Sam out, but Sam thinks you're more into Dean than him.

    Language:
    English
    Words:
    806
    Chapters:
    1/1
    Kudos:
    65
    Hits:
    812
  6. Tags
    Summary

    Dean and Cas play matchmaker for Sam and Eileen on Valentine's Day

    Language:
    English
    Words:
    840
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    65
    Bookmarks:
    5
    Hits:
    264
  7. Tags
    Summary

    Gabriel and Aylia meet after she's saved from a witch's curse. However, they have an instant dislike towards one another. Dean sees it as something else. Will his meddling help the two of them become closer, or will they fight it? And can Gabriel help her heal in more ways than one?

    Language:
    English
    Words:
    41,029
    Chapters:
    5/5
    Collections:
    1
    Comments:
    10
    Kudos:
    42
    Bookmarks:
    8
    Hits:
    750
  8. Tags
    Summary

    Requested by @murielthemagicalgirl: Reader crushes hard on Sam and works from time to time together with the boys. And she's introverted and a usually mature and serious person. But when she accidentally sees Sam without his shirt she gets hella flustered and awkward and Dean grins from ear to ear and teases her because of it until she confesses maybe that she indeed likes his brother, not knowing that said brother is standing behind her

    Language:
    English
    Words:
    1,779
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    54
    Bookmarks:
    6
    Hits:
    625
  9. Tags
    Summary

    Sam didn't get any work done that day. Nor on the next. Nor on the next. Nor on the day after that. By the end of the week, Sam accepted that he had writer's block. By the end of the month, he realised that this might be worse than anything he had experienced before. Naturally this situation had nothing to do with Eileen leaving him...

    Language:
    English
    Words:
    3,698
    Chapters:
    1/1
    Kudos:
    6
    Bookmarks:
    1
    Hits:
    134
  10. Tags
    Summary

    Paratext as paratrooper, coming to the rescue.

    Language:
    English
    Words:
    1,254
    Chapters:
    1/1
    Comments:
    31
    Kudos:
    127
    Bookmarks:
    8
    Hits:
    975
  11. Tags
    Summary

    When Castiel and Jimmy bought a shiny, brand new ship for themselves, they opted to purchase a top-of-the-line AI to help them run it. The Dual Enhanced Android unit - or D-E-An - has proved invaluable in helping them run and maintain the ship. And, as specified by his programming, Dean is determined to do whatever he must to accommodate the varied needs of his twin owners...

    Note that I've tagged "mildly dubious consent" because Dean is technically a slave/owned by the Novaks, but this isn't an angle that I play up, and I think it's pretty clear that Dean has his own personality and is making his own choices. However, as it could be interpreted as dub-con I wanted to tag for it. If knowing that's a background dynamic will make you uncomfortable, I suggest you not read.

    Series
    Language:
    English
    Words:
    2,547
    Chapters:
    1/?
    Comments:
    37
    Kudos:
    133
    Bookmarks:
    17
    Hits:
    1851
  12. Tags
    Summary

    Jimmy Novak had nearly everything he’d ever wanted; a decent job, a beautiful daughter, and a boyfriend he adored. But his father’s sudden death threatens to destroy the things he holds most dear when he’s forced to come face-to-face with his past and the one person he never wanted to have to face again: his brother.

    Castiel Novak had been managing life just fine. It hadn’t been going the way he’d expected, but still, things were fine. That was of course until his father died and he was back in the same room as his twin brother, Jimmy, and all that managing was a little harder to do. Between his brother, his memories, and his brother's gorgeous new boyfriend, Castiel was fairly certain it’s only a matter of time before something snaps.

    Dean Winchester thought he’d had things relatively figured out. He was in love and more than ready to take the next step with his boyfriend, until he found out about that twin brother his boyfriend had never mentioned. There’s some kind of damage between the two of them, shaking Jimmy up and messing with his head. Dean is determined to find out what and hopefully fix it. Now all he has to do is figure it out and not fall for the wrong twin in the process.

    Language:
    English
    Words:
    61,706
    Chapters:
    13/13
    Collections:
    2
    Comments:
    163
    Kudos:
    252
    Bookmarks:
    60
    Hits:
    3177
  13. Tags
    Summary

    "I'm sitting out dances on the wall, trying to forget everything that isn't you. I'm not going home alone, cause I don't do too well on my own."

    Teenaged Sam and Cas get locked in a closet. It lasts longer than seven minutes, but neither of them are gonna complain.

    Language:
    English
    Words:
    2,913
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    108
    Bookmarks:
    12
    Hits:
    1087
  14. Tags
    Summary

    Locked in her own home by God knows who, with no family, friends, no love, Aidan is desperate to leave the town of Canaan. In the progress she meets the two hunters who changed the world and accidently falls for the younger one. The connection between the two has mostly come from everything they don't have in common. But what they do is that they're both very very SPECIAL KIDS.

    Language:
    English
    Words:
    8,836
    Chapters:
    5/?
    Hits:
    70
  15. Tags
    Summary

    Dean keeps trying to push Benny and Sam together. It won't work.

    Series
    Language:
    English
    Words:
    387
    Chapters:
    1/1
    Kudos:
    71
    Bookmarks:
    8
    Hits:
    951
  16. Tags
    Summary

    This is an entry for WIP Adoptions, a collection of unfinished WIP's that are being put up for adoption. This is not a complete fic. If you are interested in finishing it, check out WIPAdoptions(https://archiveofourown.org/collections/WIPAdoptions/profile).

    Language:
    中文-普通话 國語
    Words:
    2,386
    Chapters:
    1/1
    Kudos:
    1
    Hits:
    101
  17. Tags
    Summary

    Sam and Dean have movie night at Sam's apartment.

    Language:
    English
    Words:
    498
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    50
    Bookmarks:
    2
    Hits:
    384
  18. Tags
    Summary

    This is an entry for WIP Adoptions, a collection of unfinished WIP's that are being put up for adoption. This is not a complete fic. If you are interested in finishing it, check out WIPAdoptions.

    Language:
    English
    Words:
    1,613
    Chapters:
    1/1
    Collections:
    1
    Comments:
    19
    Kudos:
    9
    Bookmarks:
    1
    Hits:
    248
  19. Tags
    Language:
    English
    Words:
    2,683
    Chapters:
    1/1
    Kudos:
    11
    Bookmarks:
    1
    Hits:
    256
  20. Tags
    Summary

    Barista-college!au fic. Sam and Castiel are making out in the bathroom of a coffee shop and somehow this is all Dean’s fault.

    Language:
    English
    Words:
    1,048
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    452
    Bookmarks:
    52
    Hits:
    5081

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