It was midday before Gabriel decided to put his first plan into action. It was a simple plan, he wasn't going to get extreme if he didn't need to. He only wanted Sam to go on a date with him and if Sam still wasn't interested by the end of the two weeks then Gabe accepted he'd have to leave it alone, not that he wanted to.

The first step was to get Cas and Dean to drop him off at the bakery near the library, where Sam and Cas worked, on their way to a movie, at least that's where they said they were going. The second was to enter the bakery and purchase two chocolate éclairs, Gabe had asked Cas and his brother had said that the éclairs were Sam's favourite. Dean had said that food was the way to only one Winchester's heart, and it wasn't Sam's.

Gabe headed in the direction of the library carrying two paper bags, obviously containing the delicious pastries. He was confident, as he walked, that the young Winchester would agree to go on a date with him, he knew Sam desired him at least a little bit. He could work with that.

He strolled along the path and under some jacaranda trees, their purple flowers fluttering in the slight breeze. Gabe picked one of the small flowers from a low branch and turned the corner to find the library.

Entering the building he noticed a large desk in the middle of the categorised shelves, with a small room behind it which he thought must act as a break room. Sitting behind the desk tapping at a computer was none other than Sam Winchester.

Gabriel wandered up to the desk in front of Sam "Excuse me." He started "Where can I find a book on winning the heart of an attractive male you're interested in?" He meant it as a joke but Sam hadn't looked up from his computer screen to see who it was and so answered professionally "Perhaps in the 'Adult Relationships' section you might find something. If you have any trouble let me know and I'll do my best to find what you need."

Sam still hadn't looked up from the computer so Gabe said devilishly "What if I need you?"

That got the young man's attention, his head shot up from the computer screen to find a grinning Gabriel leaning on the desk "Heya, Sammy."

"Oh, hello, Gabriel." Sam mumbled, slightly shocked by the older man's presence in their small town library.

"I told you to call me 'Gabe', kiddo" Gabe said fondly.

Sam nodded "Okay, Gabe, what are you doing in a library on your holiday, you didn't strike me as the bookworm type…"

"Well, I was looking for you, I brought pastries!" He announced as he held up the paper bags containing the éclairs, a grin splitting his face.

Sam eyed him "Why were you looking for me?"

"Because…I wanted to ask you to go out on a date with me, and I heard you like éclairs so I got you one." Gabe felt kind of nervous with Sam scrutinising him with his eyes, but he tried to keep his confidence up.

"Oh, well, um…I'm flattered, Gabe, but I'm not really looking for anyone, and I couldn't handle long distance, and…I'm sorry, it's just not a good idea." Sam tried to read Gabriel's expression to see how the older man was going to react, but he found the guy hard to read.

"I wasn't looking for anyone either." Gabe said more to himself than to Sam and the younger man gave him an odd look. Suddenly pulling his mind together Gabe spoke again "It's alright, kiddo, I've got thirteen days to get you to change your mind, I'll see you tomorrow, Sammy." With that he sat one of the éclairs on the desk in front of Sam, winked and walked out of the library.

Sam stared after him until Gabe had disappeared from sight, half of his mind was telling him he was an idiot for turning down an attractive guy who wanted to date him, and the other half was telling him exactly what he told Gabe. He reached over and picked up the paper bag apparently containing an éclair and when he opened it not only did he find an éclair but lying in the bag was a beautiful, purple jacaranda flower. Picking out the flower, Sam held it in his finger tips and felt a smile bloom on his face, that's ridiculous, the guy gives him his favourite pastry and a small flower and he's all smiles over it. Wait. How did Gabe know he liked éclairs? He had said that he 'heard' it, from who? Then two names sprung into his mind, obviously.

Sam got up and walked into the break room as he scrolled through his contacts and found 'Dean' then pressed call and held the phone up to his ear. Dean didn't answer until half way through the sixth ring "What's up, Sammy?" he sounded a little breathy but Sam ignored it.

"Are you and Cas trying to set me up with Gabriel?" No pussyfooting around, he wanted to know what this was about.

"Sounds like you said no, but it's his idea, not ours. We think he's actually really into you, though…you weren't a dick were you, 'cause we gotta live with him for two weeks."

"No, Dean, I wasn't a 'dick', he said he would see me tomorrow and that he had thirteen days to change my mind…"

"I think you should go on a date with him, you never know, you might end up liking him, don't forget you got me and Cas together."

"Yeah, but you and Cas were eye-fucking in public."

"Now we're fucking for real."

Sam could hear the smirk on Dean's face through his words "I didn't need to hear that."

"Well quit being afraid of dating and actually allow the guy to treat you for a night, Jesus Christ, Sam, he actually seems like a pretty good guy, you might be missing out on something if you don't. Anyway, it's up to you, Sammy-hang on-Cas says to come over for lunch on Sunday, he's cooking…"

"Alright, I'll come over, see you both on Sunday. Bye." Sam hung up.

So Gabriel was serious about dating Sam, Dean and Cas were telling both of them to go for it, and apparently a small part of himself wanted it too, so why wasn't he saying yes?

X X X

Dean hung up after Sam and put his phone away, he turned to Cas "Sorry, apparently your brother isn't as charming as he thinks he is, Sam turned him down, but that's probably not Gabe's fault."

They were lying on a blanket on the grass in between the Impala and a small lake, Dean's mother used to bring him here before she passed away, now it was Dean and Castiel's place to be alone together. Cas cuddled into Dean, breathing in his scent and said softly "Why doesn't Sam date?"

Dean sighed "In his last year of high school the guy Sam had been crushing on for about two years found out that Sam liked him and they dated, but he was an asshole to Sammy, and treated him like shit. The day of their graduation, the guy found a microphone and basically announced that their whole relationship was a joke and that he didn't even like Sam. Called Sam a bunch of names and him and his friends laughed while Sam bawled his eyes out. I was there, because I was watching Sam graduate, I got over to him and knocked him the fuck out. Then I grabbed Sam and we got the fuck out of there. So Sam has never dated again, even though I try to encourage him, but some stuff just screws you over. I thought maybe because Gabe is your brother he might be more open to it."

"Wow, poor Sam. I was given some trouble in high school for being gay, but that's just awful, I can understand why Sam would turn down Gabe." Cas said, clinging to Dean a little more tightly.

Dean kissed the top of Castiel's head and shook off the memories "Enough of that, I don't want to talk about Sam and Gabe, I just wanna be with you today."

"Mmmmm…sounds good, got anything in mind?" Cas asked slightly teasingly.

Dean grinned at his boyfriend "I might…"

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Hey guys, so I know it kinda got a bit dark there with Sam's past, but I hope you enjoyed the chapter anyways, let me know..much love xox