You’re curled up on the motel bed, trying to find some semblance of comfort as cramps twist through your abdomen. The day’s been rough—long drive, lousy weather, and now this. You hear the familiar sound of the Impala pulling into the parking lot, the rumble of the engine somehow reassuring. Moments later, the door creaks open, and Dean steps inside, wiping the rain off his jacket.

“Hey,” he greets, but his usual swagger falters when he catches sight of you. He tilts his head, narrowing his eyes like he’s trying to figure out what’s wrong. “You okay?”

You manage a nod, though it’s clear you’re not fooling him. He’s always been annoyingly perceptive, especially when it comes to people he cares about. Dean crosses the room in a few strides, kneeling down by the bed to get a better look at you. “What’s going on?” he asks, his voice softer now, the concern clear.

You hesitate for a moment, then sigh, deciding there’s no point in pretending. “I’m just… having my period. It’s nothing serious, just cramps.”

Dean nods, the worry in his eyes shifting to something more like determination. “Right. Got it. Hang tight.” He’s on his feet and out the door before you can protest, leaving you wondering what he’s up to.

A few minutes later, he’s back, a plastic bag in hand. He sets it down on the bed and starts pulling things out—painkillers, a heating pad, and, to your surprise, a couple of your favorite snacks. He even grabbed a bottle of ginger ale.

“Figured you could use these,” he says, handing you the painkillers and the heating pad. “And before you ask, yeah, I know my way around a pharmacy. I’ve had to do this for Sam more times than I can count. Except with him, it’s usually some weird-ass flu or whatever the hell else he manages to catch.”

“Better?”, he asks as you wash down the pills. He’s quiet for a moment, then he glances over at you, a smirk tugging at the corner of his lips. “You know, if you want to milk this for some extra TLC, now’s the time. I’m feeling generous.”