My favourite ever Dean loves Cas moment is when in s10 ep5 'Fan Fiction'
Dean 'fixed' the tie of the girl who was playing Cas- and reason it's so heart melting is because the girl was wearing the tie the right way but Cas wears his backwards so that's why Dean changed it
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Dean knocked on Sam's door; it was finally time, he decided to deal with his confusing ass feelings for Cas but he knew he needed help to do it so who better than his own brother
"Come in!" Sam allowed and Dean took a moment before he entered "Hey" His gruff voice said, and Sam looked up from his laptop "Hey- what's up"
"I need your advice"
Sam's brows knitted together in confusion "On?"
"Before I say anything- just know this is not a chickflick moment and the second you make it one I'm going right out that door"
Sam nodded awkwardly, keeping a smile from growing on his face "Okay"
Dean cleared his throat "Well tomorrow is gonna be the day me and Cas met and I kinda wanna do something special for the both of us"
Sam frowned "Oh well I didn't even think you'd remember" Dean scoffed "Of course I'd remember we've been bestfriends for almost over a decade"
Sam took a deep breath "Okay then maybe you should ask him on a date" Dean frowned "Why would I do that?" He questioned and Sam just gave him a look
"Dean we beat God- this is the perfect time for you to ask Cas out- you always find reasons to not do it, but now there's nothing going on- you can't just avoid it forever"
Dean was seriously regretting telling Sam about his crush when the angel had died, he folded his arms over his chest "How would I even do it?" He asked shyly, Sam smirked leaning back in his chair "All you have to do is ask him out and I'll take care of the rest"
"Don't smile like that" Dean said to him "-And thanks Sam"
"Hey, you deserve it"
Dean wanted to do it before he chickened out so he went straight from Sam's room to the library where he knew the angel was playing monopoly with Jack
"So how's it going?" Dean asked with a chuckle, both of them were lazer focused on the border before them "..This game.." Jack spoke slowly "It's..interesting"
Dean still could not shake how freaking similar Cas and Jack were "Jack could you give me a minute alone with Cas?"
Jack nodded leaving them, "What did you want to talk about?"
"Well..tomorrow is-"
"The anniversary of the day I saved you from hell, when we first met" Cas said for him
"Oh..so you remember- that's-" Dean cleared his throat "..I just wanted to..do you want to celebrate it I guess?" God he was not good at this
Cas nodded "Yes..that would be nice" Dean smiled "Great, tomorrow night?"
"It's a date then" Castiel confirmed and making Dean do a double take "Really?- a date?"
Cas frowned, feeling that he overstepped "Do you not want-" Dean shook his head stopping him "No- no I was just..making sure"
Cas gave a nod "So it's a date"
~
Dean looked in the mirror one last time, he'd gone with some black ripped jeans and a white long sleeved shirt with the only two buttons at the top opened
