Work Text:
Jess was delighted when Brady introduced her to Sam. Usually when a friend tells you they want you to meet their other friend, are as eager as Brady had been, and punctuate it with “I think you guys could really hit it off,” it doesn’t work out well. Didn’t set-ups only happen as awkward favors…? Or out of pity? And which of them had Brady been pitying, her and Sam? These are things she wondered before Brady lead her across the room at their mutual friend’s party to Sam and put her hand in his, by way of introduction. After that, her doubts melted away.
He was so tall, eternally tall, with this shaggy hair that fell across his forehead in little waves. She had to search under his bangs to see the nervous furrow of his brow as he shook her hand. His smile was only slightly crooked. And it was then that Jess realized Sam was just as surprised to be introduced to her as she was to him, which honestly made her feel more at ease, and coincidentally, more interested in him.
“I’ll leave you two to it,” Brady said with a smirk, then disappeared into the crowd around them.
From there, Sam grabbed them both drinks and Jess embarked on the mystery that was Sam Winchester. He wasn’t as easy to read as she would have liked. Jess wasn’t certain if the small talk they were participating in was due to Sam’s politeness or discomfort. Was he glad to be talking to her or did he just not know how to let her down easy and escape? Jess wasn’t full of herself, at least she didn’t think she was, but she was also not used to feeling this way. Unsure. It was made especially worse when she realized the more they talked, the more she wanted him to be interested.
Half way through the night they hit their stride and settled into a comfortable pace. They had talked so long, they’d both finished their drinks yet never left the conversation to get more. They didn’t need it. That was a great sign, Jess thought.
Sam made her laugh and she was able to make him laugh, and after a while Jess discovered Sam’s real voice was a bit louder and his real smile was a bit larger than before when they first met. Her confidence swelled each time she witnessed Sam reveal a little more of himself to her throughout the night, and before she knew it, the party was dying down. The two of them looked around at the crowd that had dwindled to a few small groups of friends still chattering.
“I guess I better go,” Jess said. “I didn’t realize it was so late.”
“Okay,” Sam replied, standing. “Can I walk you out?”
Jess stood, too. The hopeful look on Sam’s face reminded her of the sweetest puppy she used to have when she was a girl. It absolutely melted her heart. “Sure.” She couldn’t hide her smile.
Jess felt Sam’s hand appear lightly on her back as he kept in step behind her on their way through the trashed room towards the door, the dying party humming around them. She wasn’t sure if it was there to help guide her or keep him from being separated from her.
“This is me,” she said when they reached her car. She turned abruptly back to Sam, causing him to stop short just in front of her. It was awkward again, but Jess was sure that it wasn’t because he was uninterested, but rather the opposite. She watched him fumble a little to steady himself and think of something to say. Her heart melted a little bit more.
“It was cool getting to talk to you tonight,” he said, running his hand backwards through his hair, ruffling it a bit with his nerves.
“Yeah,” Jess agreed. She felt bolder now. “You know,” she began, as to not allow an awkward moment, giving Sam a break. “I wasn’t sure if you were interested at first.”
Sam let loose another genuine laugh. “Same here,” he replied with a chuckle. “I wasn’t sure you were interested until just now.”
Then Jess was laughing. “Well, Sam, I’m flirting with you. Right now.”
“Got it.”
“Good.”
“So, can I see you again?” He put his hands in his pockets.
“Yes.” She raised an eyebrow at him. “That was me accepting your offer to spend more time together. In case you weren’t sure.”
“I got it.” He was grinning.
“Goodnight, Sam.”
“’Night, Jess.”
He stepped back to the sidewalk and let her open her car and get in. He didn’t turn to go back inside until she started the car and was on her way down the street. Jess knew because she watched him in the rearview mirror. She felt a flutter in her stomach and knew there was a ridiculous smile plastered across her face.
So maybe there was no ulterior motive with Brady trying to set them up. Maybe he really truly believed Sam and Jess would hit it off, and was he ever right. That thought made Jess’ smile grow. It was really sweet of him to take an interest in the two of them like that.