ohhh richard.

Lucky


Pairing - Rob Benedict x Reader
Word Count - 2,552
Warnings - fluff, teasing, really, I think that’s it lol
Author - Sam
A/N - Request by @sammys-angel — Can you do a Rob x Reader where she’s part of the cast but loves to sing, but she never sings in front of ppl and one day at con, Rob passes her hotel room and hears her singing and playing guitar and that’s the moment he knew he was completely in love with her, and he walks in and sees her sining and playing guitar.

The earth was quaking
My mind was aching
And we were making it
And you shook me all night long
Yeah you shook me all night

It was the last song of Karaoke Night at the convention. You were with Jensen, Osric, Briana, Rich, and Rob next to you. You guys were rocking out to the song “You Shook Me All Night Long” by AC/DC. Jumping and dancing to until the end of the song.

You really got me and you
You and Rob pointed to each other laughing like lunatics as the music played.
Shook me all night long
Yeah you shook me
Yeah you shook me
All night long

The song and night finally ended. All of you exhausted and voices crackling from yelling all night with the fans. The rest of you walked off the stage and headed back to the green room while you waited for Rob and Rich to end the night. Osric threw you a water bottle noticing that you were starting to cough a lot from screaming all night.

“Here, catch!” he giggled chucking the bottle to you.

“Thanks Os! Did you have fun?” you sat down next to him, leaning your head on him. The two of you were like best friends, he was your confidant when Rob and Rich weren’t there. Even then, you knew you could count on Osric when it came to anything. You trusted him with one of the biggest secrets that you were holding back from the rest of the world. What was that you might ask? Nothing big, you know? Just how you had a huge crush on your other best friend, Rob Benedict.

It all started when you came onto Supernatural in season 5. You were the badass hunter chick, Scarlett, that stole Chuck away from Becky. Scarlett was pretty different compared to Chuck. You were confident, fearless, and according to Chuck’s character, “way out of his league.” Once you were introduced to Rob, the two of you instantly became friends, as you also became a series regular.

To you and Rob, the age gap between the two of you made no difference in the strong connection the two of you had has best friends. Rob was there for you when your asshole of an ex-boyfriend cheated on you, and you were there for him when his wife left him behind (side note, I love Molly, so let’s just pretend that this happened). Rob was also another reason you started playing guitar, but never let anyone hear you sing alone. It was something you enjoyed keeping private, to yourself.

Over time, it was inevitable that you developed a strong crush for the blue-eyed, scruffy-faced, loving man. You could be having a really awful day, and just hearing Rob’s laugh and seeing his smile changed your day for the better instantaneously.

“Yeah I did! By the way, I saw Rob looking at you the whole time,” he teased you.

Your face flushed with a shade of pink, and you punched him gently in the side, “Quit it Os. No one needs to know.”

“No one needs to know what?” you heard the familiar voice of Rob ask.

You spun around and stuttered while making a joke, “Oh you know, just how much in love I am with Rich!” You shot up and threw your arms around Rich, and he mirrored that.

“Oh Y/N, I love you too!” he played it off so dramatically it made the rest of the room laugh, except for Rob, but you didn’t notice.

“So Y/N, you sounded great tonight! Why don’t you sing with Rob tomorrow?” Rich suggested. That was one bad thing about Rich, he always had to open his mouth. Mostly everyone on the cast knew that you enjoyed singing, but that the only time you would do it in front of others is when there was a group of people with you, like tonight. Another issue, you may have accidentally let Rich ALSO know how much of a crush you had on Rob. Unfortunately, Rich learned that Fireball Whiskey makes you talk, and you let it out a couple of months ago. Although he was kept his mouth from saying the exact thing, he continuously has made suggestions that would get Rob and you alone.

It’s not that you haven’t hung out with Rob alone, you guys do it a lot. However, recently, it has become more difficult to withstand your feelings, and you’ve know Rob has noticed it and it kills you. Falling in love with your best friend, not so lucky when you know they don’t have the same feelings for you in return.

You rolled your eyes at him and shot him a glare, “Uhm, I’m good. Thanks Rich,” you tickled his sides, getting him back for embarrassing you.

“Awww, don’t feel bad Y/N,” Rob throws his arm around your shoulder, pulling you in tight, “You don’t have to sing with me if you don’t want to.”

Rob was always so sweet, trying to make you comfortable and happy. The only thing you could do was look into this blue eyes and smile sweetly. You stood there for a few minutes before you finally let out a huge yawn.

Rob giggled, “Well, someone must be tired. That was one long yawn.”

“You’re not going to go out Y/N?” Briana and Rich ask.

You yawn again, “Nah. I’m pretty exhausted. I’m sorry guys. Rain check?”

“You’re so lame. But that’s fine. See you later sweet heart. Rob are you coming out?” Rich waved off Briana and the rest, letting them know he was coming.

“I don’t think so. I’ll walk Y/N up to the rooms and I’ll probably just crash in there. I don’t know how you guys keep going out. It’s like 1am, we have to be up at 7am, and it just sounds like a bad idea to me,” Rob explains.

“Welp, don’t do anything I wouldn’t do you crazy kids!” Rich waved the two of you off and you turned to Rob.

“You didn’t have to do that Rob. You should go out with them,” you insisted, giving him a look of assurance.

The entire time, his arm had been around you and he giggle once again, pulling you in and giving you a kiss on your temple, “It’s alright. I’ll just walk you to our adjoining rooms and we can go to sleep.”

The both of you walked to the elevator and headed to the floor of your rooms. As you arrived to the door, you pulled out your card, but looked at Rob before you went it.

“Goodnight Y/N” he said, giving you a hug.

You reciprocated the hug by throwing your arms around his neck as he wrapped his arms around your waist tightly. Squeezing and holding you a little bit longer then normal. You really didn’t want to let go, but the feelings you had for him were bubbling up inside you. You were the first one to pull apart, and both of your faces only mere inches apart. The anticipation was killing you, but knowing he didn’t feel the same, made it worse.

“Well, night Rob,” you rush and push through the doors.

Rob stood as the door closed. His heartbeat racing and face heating up from the two of you being so close. The two of you had hugged and been close for years, but now, it was different. Rob was normally able to tell you everything, but recently, he started feeling something different with you. There were feelings of butterflies in his stomach, and like every other time, he decided to just shake them away, letting them linger in the back of his mind.


The next day, you woke up, got ready, and grabbed some coffee before your panel. You loved talking to the fans and they always made you laugh. However, it never failed that at least one question was about you and Rob.

“Hi Y/N, I just love your character Scarlett. She gives me the power and mindset to be strong and confident, and I think Scarlett and Chuck are adorable together. A lot of us wish they would bring Chuck back,” the young girl was dressed as your character. A typical “Winchester” look. Plaid shirt, rocker shirt underneath, skinny jeans, and black converse.

“Aww thanks! I love to hear when my character encourages others to be their very best. As for Chuck, I think Scarlett would love to have Chuck back,” you giggle.

“So my question is this. We know that Scarlett and Chuck had hinted that they were once a couple, but never told anyone, do you think you and Rob would ever be more then friends?” she asks.

The whole place went quiet. You yourself didn’t even know what to say. “Well my darling, Rob and I are just best friends. Yes I love him as a friend, but my true love goes to Rich,” you laughed making a joke, “Ohhh Richard! Where are you my Knight in Shining Armor?!” All you wanted was to be saved from this question and Rich knew you would want it.

“Alas! The princess calls for me! It’s the ending of her panel, I shall save her,” he scoops you up and you blow kisses to the fans as they laugh and scream in hilarity. He runs to the back as Misha and Jared enter the stage after you.

You let out a huge breath and hug Rich, “Thank you so much for saving me from that. I have no idea what I would’ve done without you.” You look him in the eyes with seriousness and he notices that the situation caused you anxiety. Rich could’ve made a joke, but didn’t.

“No problem Y/N. You know I care about you,” was simply all he said. There was nothing else that needed to be added, as he hugged you back.

“Well, I’m going to go to my room and relax until my photo ops,” you said waving him off and heading to the elevator.

“Hey, Rob! Are you ready for lunch?” Rich asked, noticing Rob coming from the other side of the stage.

“Yeah, I think so,” he said reaching in his pockets, “Shit. I left my wallet in the room. I’ll be back in 15.”

You went into your room and grabbed your guitar. Rob had given you lessons years ago and you continued to pick up on some tricks from him and other musicians. You began to strum the chords to a song you recently learned to play, and sing.

Do you hear me, I’m talking to you
Across the water across the deep blue ocean
Under the open sky, oh my, baby I’m trying

You start off slowly, taking in the music and string as you play the melody of the song. You get lost in your own little world, not noticing that someone was listening and peaking through the door from your adjoining room.

Boy, I hear you in my dreams
I feel your whisper across the sea
I keep you with me in my heart
You make it easier when life gets hard

Rob entered his room, rummaging around near the adjoining door where his bags were and tried to find his wallet. That’s when he heard it. Music was coming from your room. At first he thought it was just the TV, but that was too loud. That’s when he snuck his way through the doors and opened it up.

Lucky I’m in love with my best friend
Lucky to have been where I have been
Lucky to be coming home again

He stood there listened as you sang. He knew it was wrong, but he couldn’t help it. Your voice was amazing and your guitar skills had definitely gotten better. He couldn’t help but smile as you played. The way you sang to the melody was perfect, and the lyrics, well, created a final connection in Rob’s brain. He was in love with his best friend.

They don’t know how long it takes
Waiting for a long like this
Every time we say goodbye
I wish we had one more kiss
I’ll wait for you, I promise you, I will

Hearing your voice as you sang was the final link for him. Rich was right, he did love you and have feelings for you, but was afraid that it was just a fluke. But oh boy, was Rob’s logic wrong. Rob knew he had to do something. He couldn’t stand this any longer, and he knew the song so when you started the next verse, he walked in singing along, creating a harmony with you.

Lucky I’m in love with my best friend
Lucky to have been where I have been

You heard a voice that sounded familiar and Rob appeared in front of you. You began to slow down.

“Don’t stop Y/N, please,” he says to you with eyes of encouragement, so you continue, just the two of you.

Lucky to be coming home again
Lucky we’re in love in every way

Rob and you looked into each others eyes, pouring emotion into the song as you both sang to the words.

Lucky to have stated where we have stated
Lucky to be coming home someday

You both sat there, finishing the chorus, staring at each other in silence. His confidence growing as the moments went on, he grabbed the guitar and put it behind the both of your, and then grabbed your hand.

“Rob,” you whispered, feeling the heat of red form on your face again, darting your eyes to the ground in embarrassment.

He put his hand on your chin and tilted you back to face him, “Hey, no, don’t look down. Don’t be embarrassed,” he breathed out, “Y/N, your voice, it’s beautiful, just like you are. I can’t believe..” he trailed off, becoming nervous and losing his confidence.

You looked at him confused, “Can’t believe what Rob?”

He looked back into your eyes, almost losing himself in them, “I can’t believe it took me this long to realize I’m in love with my best friend.”

Your mouth falls slightly agape in shock that Rob just admitted his love for you, but you couldn’t hold back the next thing you were about to do. You lean into Rob and pull him in for a kiss. Your lips land on his and all you could feel were sparks, his scruffy beard, and it was only the two of you. Nothing else mattered or existed. You felt him sigh in to the kiss, as if it were relief for him as well.

After a few moments of exploring each others lips, you pull away and smile, “I’m in love with my best friend too Rob. You, and I have been for years.”

He wiggled his eye brows and giggled, touching your face softly, “Well, I guess the song does ring true. We’re both lucky to be in love with our best friends.”

You smiled again unable to fight the urge and pulled him in for another long kiss, because you weren’t about to waste anymore time not kissing the man you loved most, your best friend.


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