HI MARI !!
IM HERE WITH MY DEAN THOUGHTS!! (mostly platonic)
when you become friends/best friends, he’s ride or die for you
not on the same level of sammy but it’s a close second
the playful banter between the two of you is just great
although he knows that he can be annoying and uses it to his advantage
flirting with you to annoy his brother (he knows that sammy is in love with you and does it to get on his nerves)
PET NAMES!
has a reserved nickname for you but does pull out the pet names if you’re having a bad day
speaking of bad days/sick days
he will go out of his way to take care of you
pulls out all of the stops for his bestie
this is when you realize this man is a secret softy at heart (refuses to admit it, because he’s a “big bad hunter”)
platonic cuddles/casual physical affection
dean is reserved with physical affection (im thinking post hell! dean) (earlier szns dean wouldn’t hold back tbh)
but once he’s comfortable with you (and is sure that you won’t leave him or sammy)
then it’s a free for all
swinging his arm over your shoulder, sharing a bed if there’s only two beds (sam seethes sometimes but this is way before you guys get together lol), resting his head in your lap during movie nights (starts off as a joke wanting to annoy you but then does it almost everytime you guys have one, loves when his hair is getting played with)
there’s def more but ill cut it off here (i love bestie dean but im also in love with him LOL) (the winchester brothers have a GRIP on me)
HELLO DAISYYYY HEHEHEHE this is amazing i'm so obsessed <33
cw : mentions of injuries, pet names obviously , dean is annoying ofc <3, sammy and reader like each other, swearing probably, alcohol mention, unedited! wc : 1.5K
⟢ ride or die : i mean yeah, this is pretty much undeniable. sure, sam will always be his first priority, but the moment he knows that you're a part of the team, no doubts, he's prepared to do just about anything for you. both fortunately and unfortunately, this does mean he gets really protective of you similarly to how he is with sam, especially if you're younger than him. and even if you're not, the fact that you're his best friend makes you family, and we know how dean feels about family <3
⟢ playful banter : this is basically just your whole friendship with him HAHA. not truly, of course, but mostly heh. like idk what else to say, he'll take any opportunity to tease you or make you fake angry because he just thinks it's too funny. and he'll love whatever way you respond to that. he definitely enjoys if you return his fire with your own teasing and retorts and i personally think you are so allowed to be mean to him because he's an idiot!! obviously don't be actually mean, but he enjoys having a teasing relationship where you can call each other stupid and know that the other means it with love lol.
when the two of you get into it, sam gets so annoyed. like you'll be arguing about the value of mustard on sandwiches and both of you are so invested in winning the argument and sam is like oh my god, dean please focus on the road and shut up, both of you😭😭 the boy is trying to sleep, he doesn't need this right now. so you either keep arguing in hushed tones (which doesn't last for long) or you pick it back up at another time (that's also probably inconvenient and annoying to sam still HA).
and yeah, dean can be very annoying and he loves to rile you up LOL. it's great when you reciprocate his banter, but sometimes he's just so ridiculous that it has you rolling your eyes and groaning in frustration. and unfortunately for you, that, or any other dramatic response, is exactly what dean is trying to get out of you. "dean, will you shut up?" is one of his favorites. he just laughs at you, he thinks the way you say it is so funny and cute.
he does other annoying things too, like rest his elbow on your head or shoulder if it reaches, he doesn't care if you're his same height, barely shorter, or significantly shorter, he's gonna make fun of your height. and if you're taller, yeah he's still gonna make fun of that, too. he'll playfully put his hand on the top of your head, just for the pure intention of annoying you. idk basically anything that annoys you, he does it (usually without going overboard, he knows where to draw the line).
and yeah, the flirting is more about annoying sam, but it's a total plus when you give him that look saying, "really, are you kidding me?" he'll love a good banter on that end of the spectrum too, if you're down for flirting back. unfortunately, this sends sam the wrong message for the longest time, but it's not your fault that you don't know that he likes you back! you're just playing around with dean heh.
⟢ pet names/nicknames : yes yes yes!! he absolutely has a nickname that is specific to you!! basically your version of "sammy." it might be a nickname based off of your given name, but it totally could be an inside joke, something silly and cute. it might even be a pet name that he uses for you exclusively. i can see him calling a younger best friend "pumpkin," mostly as another method of annoying you. that one is used pretty sparingly though because it's a little over the top for the both of you. he definitely uses it a lot less than whatever his main nickname for you is, which he uses just about all the time lol. if you have a nickname based off you name, sam probably uses that, too. so, dean likes having a separate nickname that he came up with which only he uses.
and yes! he does use pet names casually and occasionally, but he's far more likely to use them if you're having a bad day, if you were injured on a hunt, or something like that! i think maybe this is just because i'm obsessed with the time that dean called lisa honey once, but i think the idea of dean calling his best friend honey is really adorable. that one is used for maximum comfort, especially if you're injured <3 "c'mon, honey. keep your eyes open, you're okay." i can also see dean using baby platonically sometimes!
he does occasionally use over the top names like sugar plum or honey bunches to annoy you lol. he will "sweetheart" you in a teasing way because he loves the way it makes you fume LOL. but in special circumstances, he'll call you sweetheart sincerely (also more likely when you're injured—"you're alright, sweetheart, we're almost to the motel"). idk if this counts as a pet name, but he'll definitely call you kid and kiddo if you're younger than him like how he does with charlie <3 i see him using darlin' very casually! "alright, c'mon darlin', let's see what sammy found." casual pet names means he's in a good mood though. he also will use insults like pet names because you're his idiot best friend <33
he won't tell you this but he likes if you've got a nickname for him, too! but he will tease you if you try to use the same pet names for him, even if you're casual about it in the same way he is.
⟢ taking care of you on bad/sick days : uhm yeah, he tries not to be obvious about it, but when he goes the the store just to pick up your favorite treat or kisses your forehead like fifty billion times when he thinks you're asleep, there's no way you can miss what a big softie he is. if the way you wear your hair allows, he'll brush any stray strands out of your face, especially if you're sick and it's stuck to your face with with sweat. checks your temperature on your forehead with his hand <3 then if he thinks you have a fever, he busts out the thermometer and takes your temp that way just to make sure you don't have to go to the hospital. he brings you your meds and lovingly bothers you about eating enough food. makes you watch movies with him lol
on days that are simply just bad, well, he's horrible with emotions, but he knows that pie and alcohol can fix almost anything (this is not true, but it still helps you to have a treat and a drinking buddy). while he's bad with emotions, he is absolutely more than willing to listen to anything you need to talk about. he's not sure how to tell you that he's there for you out loud, so he'll pour you another drink if you're not too drunk and rub your back with a soft, but firm hand. his go to phrase to comfort you is, "we'll figure it out," and it works because you know he really means it, and he says it in a soft and sweet tone that's quite rare for him.
⟢ physical affection : he can definitely be more reserved sometimes with touch, but he welcomes any physical affection that you initiate. if you purposefully stand shoulder to shoulder, he'll put his arm around you, and he'll certainly accept any hugs you have to offer. like you said, once he's even more comfortable and confident in your being around, he's much more open about swinging an arm around your shoulder and any given moment (especially because he can shove you around a little that way lmao).
he's definitely okay with the bed sharing, mostly because it's a necessity, though he tries to get you to share with sam much more once he realizes that you like each other because he can see sam physically become upset when you share with dean lmao.
movie nights are prime time for physical affection with dean!! i definitely agree that he puts his head in your lap first to annoy you, but when you don't bat an eye and start running your fingers through his hair, he's done for. he always is trying to get you to do it again, every time you watch something together, and that's when it gets annoying lmao, because he won't let you rest your head on his shoulder anymore or let you be the one to put you head in his lap. he'll make an exception if you're having a bad though hah. once again, he will dial down the cuddles if he can tell that it's bothering sam, but will absolutely not give up the physical affection with you because he thinks sam needs to get over it LOL. because, at the end of the day!! you'll always be his best friend, and he will always respect you and your relationship with sammy.
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