Matchmaker Sam

Tag · 45 works

25 works open to everyone here carry this tag; 96% are complete. The average one runs about 8,800 words. Read any of them in your browser, save it as an EPUB, or listen to it.

Works

Some results are potentially explicit

Supernatural

grip them tight and

by Flux

Dean and Cas have been at each other's throats for years, but Anna and Sam are determined to change that for the better. With a well-placed love letter and some careful direction, they manage to get the two into a semi-antagonistic, fiercely competitive, and emotionally confusing game of relationship chicken. Now they just need to get to prom.

Teen 20k words 1 ch Complete 3.6k kudos

Alternate Universe - High School · Jealous Dean Winchester · Jealous Castiel · Matchmaker Sam· +7 more

Supernatural

Father Material

by almaasi

All Castiel needed was someone to babysit his troubled four-year-old niece while he went out to dinner with Sam. Honestly, after everything he'd heard about Sam's older brother, Castiel wasn't expecting Dean to be capable of handling the job. But not only is Dean highly competent, his skill with difficult children makes him appear downright charming. Improbable as it is, it's starting to look as though both Castiel's sanity and romantic life could potentially be salvaged by just one man.

Teen 12k words 1 ch Complete 1.9k kudos

Alternate Universe - Human · Castiel & Sam Winchester Friendship · Babysitting · Children· +15 more

Supernatural

ThankYouSammy

by almaasi

@honeybeeinatrenchcoat: First official date with Dean! Sam made spaghetti bolognese! I don't eat, but Dean does :-P #ValentinesDay2015 #ThankYouSam

Teen 9.6k words 1 ch Complete 1.2k kudos

Valentine's Day · Fluff · Matchmaker Sam · Sam Ships It· +13 more

Supernatural

Fish Are Friends, Not Food

by riseofthefallenone

As a favour to Sam, Dean goes on a date with one of his university friends. He barely knows Cas beyond the fact that he finds him attractive and he's Sam's friend. He definitely didn't know that Cas is basically a goddamn fish whisperer.

General 2.1k words 1 ch Complete 924 kudos

Fluff · Matchmaker Sam · Pre-Relationship · Staggered Timeline

Supernatural

Overused Plot Device

by OsirisApollo

When the new case is at a hotel currently booked by a couples only event, the boys decide to bring in reinforcements. 'Dean had known it was a terrible idea the moment his brother agreed to play the gay couple at the retreat. He should have said something the second he realized denying himself the opportunity to play happy couple with Castiel would mean that his brother would be the only other option. He should have just agreed to partner with Cas on this case from the beginning. But his stupid fucking pride had told him he couldn’t spend an entire week pretending to be gay, and he had listened. Because he was an idiot.' UPDATE: Now contains art!

Teen 40k words 13 ch Complete 796 kudos

Sam Ships It · Charlie Ships It · Dean In Love · Castiel In Love· +25 more

Supernatural

Code Red

by orphan_account

"Cas! You're our wedding planner?" "I guess I am." Cas says as he reaches out to shake the alpha's hand. The second their hands meet, he feels it; that same old spark that he used to feel every time his childhood crush had so much as looked at him.

General 2.1k words 1 ch Complete 443 kudos

Alpha/Beta/Omega Dynamics · Alpha Dean Winchester · Omega Castiel · Beta Lisa· +8 more

Supernatural

Death Valley Queen

by Aerlalaith

Dean marched over to the rose bushes, nestled together in a circle well within the adobe shade of the anthropology building. Sam followed at a more sedate pace. When Dean’s boots toed the edge of the dry mulch, he placed his hands on his hips. “Cas,” he said flatly. “What are you doing, man?” Castiel, on account of the fact that he lacked any sort of dignity, was less standing next to the rose garden and more crouched in the middle of it. He peered up at Dean. “I’m taking photographs of the flowers,” he said. “Cas,” Dean said, “get out of the garden.”

General 7.4k words 1 ch Complete 410 kudos

Fallen Angel Castiel · Gay Panic · Camping · Fluff and Angst· +11 more

Supernatural

Sam Winchester Assisting

by PrepareToBeMildlyEntertained

“I’m in love with Dean.” Sam sits frozen in place. His brain isn’t working properly and Castiel is just staring at him that way he does, which bothers everyone but Dean. Angel-of-the-Lord Castiel has just declared that he’s in love with Sam’s brother and there is no appropriate way to respond to an announcement like that.

Teen 7.5k words 2 ch Complete 330 kudos

Humor · Sam fucks up a lot · but tries his best · Matchmaker Sam· +3 more

Supernatural

If You Want Something

by PetrichorPerfume

Gabriel and Sam try to force Castiel and Dean together with varying degrees of success. God ships it, and Death doesn't have anything better to do.

Teen 779 words 1 ch Complete 318 kudos

Sam Ships It · Gabriel Ships It · God Ships It · Death Could Honestly Care Less· +8 more

Supernatural

Gold and Green

by RhymePhile

Alternate Reality set directly after the finale of Season 8. Sam is recovering from the Trials when he learns Cas hasn't made it back to the bunker after falling to Earth. As Christmas approaches, Sam knows his brother needs Castiel in his life, even if Dean doesn't realize it.

General 6.6k words 1 ch Complete 285 kudos

Alternate Reality · Schmoop · Fluff · Christmas· +11 more