i know you're not on the sam/max train or anything but if dean did hook up with tasha that would certainly make things... interesting for sam and max ahahaha (SAMMY I'M YOUR NEW STEPDAD) (DEAN NO)
(oh lord Jess)
Sam and Max aren’t–a thing. At least, Sam’s… pretty sure they’re not a thing. He’s not really positive, either way. Max is only six years younger than him but somehow it seems like a whole generation’s between them, especially when Sam picks up his phone and there’s a random string of emojis that he truly doesn’t understand. He tried Urban Dictionary for one text and got nowhere, or at least nowhere helpful; a test post on reddit was met with a string of puns and then a deeply confusing set of responses, which he also Googled, and ended up so red-faced at the results that Dean asked if he was having a heart attack, or something. Flirting aside, he and Max kissed once, and then two months later exchanged a flurry of flirty texts, and they still haven’t actually… done anything. Sam doesn’t know if Max is even really interested, or if he’s really all that interested, but it’s sort of fun, regardless.
“You cannot sleep with Tasha,” Sam hisses, pulling Dean out into the hallway.
Dean raises affronted eyebrows, but he’s not bothering to hide his grin. “How dare you,” he says, all wide and toothy. “We are just having a pleasant, adult conversation, and it is a–an affront that you think–”
“You’re the worst person I know,” Sam says, glancing back through the open doorway. Max tips his wine glass Sam’s way, with a tiny smile that shouldn’t be nearly as hot as it is, and Sam tries to smile back, but Tasha’s looking their way, too. Dean’s way, anyway. “Seriously. Isn’t she, like, Mom’s age?”
Dean’s grin flickers for a second. “Ugh, don’t talk about Mom in the same breath as–” He shudders, exaggeratedly, but then glances over his shoulder and finds Tasha smiling at him. He winks at her, all shame instantly gone, and then turns a serious look on Sam. “I’m not an ageist, Sammy. I am surprised at you, really. All ladies deserve to have a good time, no matter how–”
“Old?” Sam cuts in.
“–matured,” Dean continues, unruffled. He lifts his wine glass. “Like a fine wine.”
“Or a cheese,” Sam mutters, and folds his arms over his chest.
“See? I love cheese.” Dean’s grin goes wicked. “What, you worried that I’m going to cut into your date?”
“What? What date?”
Dean snorts. “Like the bartender’s real. You are not nearly as sneaky as you think you are, Sammy.” Sam opens his mouth, closes it. “Yeah. This is like that time in Duluth where you thought you were keeping your little middle-school girlfriend a secret. I can see right through you, baby bro.”
Sam pokes him in the chest. “Don’t–be weird, okay, it’s not–”
“No, no!” Dean says, expansive. He claps Sam on the shoulder. “I think it’s cute, you know? Me and your new mother-in-law will be very proud. You kids just be sure to use protection, and don’t come home too late, okay? I think we’ll be setting a curfew.” He glances again at Tasha and then starts to back up into the room, making a delighted face at Sam, whispering, “But not too early, either, you know? Mama and I need some private time.”
Dean’s gone and back in the room before Sam can smack him. Max glances his way, inquisitive, and Sam hopes that his weird shudder of revulsion doesn’t show on his face. He steps back into the room and picks up his wineglass, keeping his eyes turned well away from where Dean’s very obviously flirting with the mother of his–maybe-booty-call. He takes a deep swallow of wine.
Maybe he can bring himself to kill Dean. Sure, they’re soulmates, but some things shouldn’t need to be borne.