Friends' Lives (Sam & Dean Winchester)

Chapter 2

Written by me & destiels_sidewalk 💗

Dean watches as Jass and Ray leave the cafe, both him and Sam waving them goodbye.

Honestly Dean was a bit nervous and worked up about something but he's never talked to anyone about it, he's planning to talk about it with Sam though, after all he's his little brother.

Dean looks over at him and smiles "So, do you have any plans for the future? I mean you can't just work as a lawyer forever" He says as he takes a sip of his coffee

Sam watches them leave smiling to himself before looking at him brother and taking a sip of his coffee as well.

Honestly, he wants to have a family. Especially with Ray, he loves her. But he's too scared to tell her.

"I don't know, man. Finding the perfect woman, getting engaged, getting married, have a nice house and get children. That are my plans, what about yours?" He smiles at his brother

He smiles as he hears what his little brother says, he has always wanted the best for Sammy. He's been watching over him ever since he was a kid and he just wants him to be happy.

Dean has always known Sam had a crush on Ray but he never said anything, he wanted them to take their time and figure things out on their own.

"My plans are about the same as yours, finding the perfect woman which I already have" He says with a smile as he thinks about Jass "And then there's the next step, which is getting engaged and... I'm going to propose to Jass, Sammy" He says beaming, slightly nervous of what Sam will say but still happily smiling.

Sam smiles as he hears him talking like that about Jass. Jass was the one, who changed Dean into good. Dean was a hooker like a manly whore and Sam is so happy that Jass was able to change him and actually made him fall in love with her.

He smiles brightly at Dean as he hear him say that he's going to propose. "This-this sounds so amazing!" Sam exclaims and pats Dean's shoulder.

"Honestly, I thought I was going to get married first since you've been a hooker all these years back." he chuckles and Dean shoots him a glare, making him laugh even more.

Dean smiles, happy that he told his brother and got his approval. It's not like he needed it, he knew Sam would always support him but it's just nice to see his little brother is happy for him.

"Hey I wasn't a hooker!" He says defensively and hides a grin. "I was just pleasing myself." Sam rolls his eyes at his comment but still smiles at him.

"Either way, that's in the past. I'm just so glad I found Jass, she really has turned me into a better person." He says and smiles to himself as he thinks about how much he's changed since he met her.

Sam smiles at his brother and pats his shoulder one more time. So his brother is really getting engaged? He is so so happy for his brother, but he's wishing for that step in his life too.

He wishes he would finally man up and tell Ray how he feels, but still he's too scared he would ruin their friendship. She means so much too him, he doesn't know how to describe.

"I remember that party, you and I were going. You tried to-" Sam begins to laugh at the memory "-hook her up, but she dumbed you. Your expression then, was so priceless." he laughs and Dean rolls his eyes.

"Anyways-" Sam begins as he gathers himself "-do you have already have a ring, if yes show me." Sam says excited and claps his hands.

Dean smiles shyly "That's the thing... I was thinking maybe you could help me pick out the ring?" He asks, hoping he would say yes.