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The Reluctant Matchmaker

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Two months of strained conversation, thick silences and stilted laughs. Two months of avoidance and lonely lunches. Two months of Sam Winchester slowly losing his mind.

Ever since Gabriel's party, Sam had been miserable. The first day back at work after the party was…awkward. Gabriel always came into the office like a ball of energy, making the receptionist and secretary laugh, always bringing them little treats like a flower or one of Joshua's cinnamon rolls. Without fail, he would always bring Sam's favorite coffee with a smile and a flirty innuendo that Sam would chastise him for, but it would only make the paralegal smile even more.

Now Gabriel was like a faded version of himself. He still brought little gifts in for Becky and Linda, but he quit bringing Sam coffee and his smiles never reached his eyes.

Sam hated it. He wanted the old Gabriel back and he knew it was his fault for the change. Dean was right…he was interested in Gabriel but was too scare to admit it. Sam had it all planned out to talk to Gabriel, tell him Lilith was strictly his friend and get the nerve to ask the guy out for a drink.

Every time Sam was posed to do just that, the words would get stuck in his throat, his chest would tighten with panic and the words would be left unsaid.

And now Dean was frustrated with him and wasn't shy about telling him about it last Sunday during their lunch at Tessa's.

"You're miserable, Gabe's miserable…just tell him already! Surely you're not still hung up on the whole "I like guys" thing now, are you?" Dean asked, pausing in the act of devouring his burger. Sam was kind of surprised he was getting any attention from Dean with the burger in front of him.

When Sam didn't respond, Dean's intense green eyes bore into Sam's until Sam started to squirm in his seat and look away.

"Sammy, be up front with me. Does being gay really bother you that much? Does it bother you that I'm gay? I know Dad was ashamed when I came out, but I never thought you would be."

Sam's head snapped up at the hurt tone in his older brother's voice. "Of course not, Dean!" he reached across the table to grip his brother's shoulder. "You know I'm not Dad. I could never be ashamed of you. You raised me, the things you sacrificed to give me a better life…god, I'm proud to have you as my big brother."

Sam felt the sting of sadness that Dean would think Sam was ashamed. He remembered their dad's reaction and how Dean promptly went back into the closet, started chasing girls in hopes their father would forget about Dean's confession. It killed Sam to watch his brother play a role designed by John because their father was a closed minded bastard. It was years after John's death and Bobby's gruff but patient insistence for both boys' happiness that Dean fully came out.

"So, what you're saying is that me being gay doesn't change who I am or my self-worth? It doesn't make me better or worse than anybody else because it's one's actions that make character, not whether they like tits or dicks…do I got that right, Sammy?"

Sam leaned back in his seat and stared at his brother in amazement as Dean's face broke out in a chesire smile. The insightful bastard played him, but he was absolutely right. Dean was playing the same tricks on him that Bobby had played on Dean, years ago.

"God help me Dean, but I like him. He's been under my skin since the moment I interviewed him. I kept telling myself I hired him because of the amazing experience he had, which is partly true, but I just wanted to be able to see him every day." Sam said into his salad.

"Look at me, Sam." Sam raised his eyes to find his brother sitting forward, his eyes trained on his face. "Tell him, Sam. The guy is crazy about you. Nobody important to you is going to look down at you for having feelings for a guy. Hell, they'll probably be relieved. I know Bobby and I will be."

"Bobby knows?" Sam blanched. It was one thing to talk to Dean about it, but Bobby was the closest thing he had to a father…

"Sammy! Quit freaking out, Bobby's not blind. He saw it the last time he came for a visit. He doesn't care who you like just as long as you're happy. You of all people should know this."

Sam let out a relieved breath that turned into a chuckle. "I'll talk to Gabe tomorrow."

"Good. Now eat your rabbit food." Dean smirked at Sam's salad as he picked up his burger.

It was now Friday morning and Sam has yet to talk to Gabriel because he'd called off all week. Sam was worried since Gabriel never missed work. Every time he asked Becky if Gabriel was coming in, she would just shake her head and tell him he was still sick. Sam had started to go to Gabriel's apartment one night until Castiel stopped him, telling Sam to give Gabriel a little space.

So it was to his surprise when he walked into his office on Friday morning to see Gabriel already waiting for him, looking nervous.

"Gabe, you're back. Hope you're feeling better." Sam said, smiling but the smile slipped away as Gabriel continued to look away from him. His eyes shifted to the envelope in his hand. Sam suddenly felt cold with dread as he watched Gabriel shift from foot to foot.

"Yes, Mr. Winchester, I feel much better." Sam's brows rose at the Mr. Winchester part but remained quiet, feeling that Gabriel had more to say.

Gabriel cleared his throat. "I wanted to give you this. It's my resignation. I feel it would be best if maybe we didn't work together anymore."

Sam stared at Gabriel's outstretched hand holding the envelope but refused to take it.

"No."

Gabriel looked up in surprise at Sam's short but vehement reply.

"No?" Gabriel, who was the most confident man Sam had ever met, just stared up at him, unsure.

"I refuse to take it." Sam stubbornly, crossing his arms over his chest.

Gabriel looked flabbergasted before the look turned to anger. "You refuse to take it? I'd thought you would be happy to get rid of me since all I seem to achieve is making you uncomfortable." Gabriel hands waved around wildly as he took another step closer to Sam.

When Sam continued to just stare at him, Gabriel became more agitated

"Are you going to say anything? No, of course not! You'll never acknowledge this thing between us. You'd rather pretend it didn't even exist." Gabriel's voice rose as he turned around and walked toward Sam's desk, slamming the letter down with a slap of his hand.

"God, I can't believe I'm half way in love with a man that's so far in the closet he might as well be in fucking Narnia!"

Sam felt his stomach swoop as he stared at Gabriel's back.

Wait, Gabe might actually love me?

Instead of the panic he thought he would feel at such a declaration especially since he hadn't sorted out his own feelings for Gabriel, he felt his whole body lighten with elation.

Then Dean's words came back to Sam.

it's one's actions that make character…

Actions. Sam might have failed to put into words what he felt about Gabriel, but he sure the hell could show him.

Gabriel had turned around, leaning against Sam's desk waiting for any sort of response. Sam smiled slowly and stalked toward the paralegal whose golden eyes were narrowed suspiciously at Sam's smile.

Sam didn't miss the hitch in Gabriel's breath as Sam crowded into his personal space, trapping him between the desk and his body.

"What are you doing?" Gabriel asked, his gaze flickering between Sam's eyes and his mouth. When Gabriel licked his lips nervously, Sam groaned, leaned down and captured Gabriel's mouth.

Gabriel's body went stiff in surprise before melting into Sam's body, his hands grasping at the lapels of Sam's suit jacket.

Sam wrapped his arms around Gabriel's waist, pulling him flush with his body. He swiped his tongue along the paralegal's lips until they opened. Sam stifled his moan at his first taste of Gabriel's mouth. He tasted of cinnamon, vanilla and something that was uniquely Gabe.

Sam had just started to lick into Gabriel's mouth when Gabriel tensed and violently pushed Sam away. Sam swallowed at the thunderous look on Gabriel's face.

"What the fuck Sam? You think this is okay? You just coming in here and kissing me after months of torturing me? God, you're such a prick." Gabriel panted out before he grabbed Sam's tie and smashing their lips together again.

Sam laughed into Gabriel's mouth which Gabriel promptly bit the lower lip eliciting a moan from the taller man. Sam leaned into Gabriel, causing him to fall back onto the desk, papers scattering all over the floor.

"God Gabe, I'm so sorry, please, let me make it up to you." Sam groaned out between kisses, Gabriel's hands already un-tucking Sam's shirt from his pants and wiggling them underneath the dress shirt to glide up his sides.

"Don't think I'm going to forgive you so easily, Winchester." Gabriel growled as a fingernail scraped over a nipple making Sam shiver and moan.

"I wouldn't-" Sam gasped for breath as Gabriel started to suck on his neck, "-think you would."

"Mr. Winchester, your first client is…oh!"

Both Sam and Gabriel looked up in horror to see a wide-eyed Linda Tran staring at the mess of limbs and undone clothing on Sam's normally orderly desk.

"Ah, Mrs. Tran, I'll need a moment to consult with Mr. Milton before I talk to…" Shit, Sam couldn't remember who he was supposed to be speaking with today.

"Harold Travoy." Gabriel whispered as he hastily straightened his clothes.

"Ah, yes, Mr. Travoy, of course. Please offer him some coffee and let him know I'll be with him shortly."

Sam didn't have to see his face to know it was red, he could practically feel the heat radiating off of it. He was so busy buttoning and tucking in his shirt that he missed the smile twitching on Linda's lips.

"Of course, sir. Please take your time." Linda stated simply, shutting the door firmly behind her.

As soon as the door clicked shut, Gabriel started to laugh. "This is not what I expected when I came in today."

Sam shot him a shy glance, not knowing how to proceed. Gabriel was the first man he had ever kissed and it wasn't done with the finesse that he had imagined such like after Sam taking Gabriel on a proper date. Not in his office on an early Friday morning.

Gabriel must saw by Sam's expression what he was thinking. "I think that was most perfect argument to get me to stay. However, I think we need continue our research to see if there is adequate evidence to actually keep me. How about tonight?"

Sam huffed out a laugh. "I believe that is an excellence suggestion, Mr. Milton. Tonight will be good to do some research. We have to thoroughly explore every possibility and position. We'll have to really go in deep and quite frankly, it could take all night."

Gabriel threw his head back and laughed. Sam listened to his infectious laugh and wondered how he was able to resist the man for so long.

Well, Sam was done with resisting, especially when Gabriel smiled at him.

This time, the smile reached his eyes.