You and Dean had just wrapped up a case at Oak Park Retirement Home. Along the way, you’d met Mildred, a resident who had helped out with the case. She’d spent most of the time shamelessly flirting with Dean, which you found hilarious - and despite everything, you’d both developed a soft spot for her.

You lingered by the Impala as Dean said his goodbyes to her. You pretended to scroll through your phone, but your ears didn’t miss a thing as they spoke.

“So, you’re off on the road again, huh?” Mildred asked, her voice light.

“Yes, ma’am,” Dean replied with a small grin.

She gave a theatrical sigh. “Well, I suppose it’s for the best. Wouldn’t have worked out between us anyway.”

Dean chuckled. “Why not?”

Mildred leaned in just slightly, her tone turning playful and warm. “Darling… if there’s one thing I’ve learned in all my years, it’s when somebody is pining for someone else.”

Dean went quiet and you froze, not looking up from your phone even though you wanted to.

Mildred laughed gently. “Oh, don’t bother trying to hide it. It’s in your eyes. Every time she walks into the room, it’s like the rest of the world disappears.” She placed a hand gently on his chest. “Follow your heart.”

Dean cleared his throat, forcing a chuckle. “Well, uh... you’re wrong. I’m single and ready to mingle.”

“You might be single, but honey, you are not ready to mingle. Now if you’re smart, you’ll stop pretending there’s nothing there.” Her voice dropped a little quieter “Some people are worth the risk.”

“Okay, well- uh, thanks for the advice,” Dean said, voice a little rougher than normal.

She patted his chest once and smiled, stepping back. “Drive safe, sweetheart.”

At that, you glanced up from your phone, just in time to see Dean heading toward the Impala. He didn’t look at you as he slid into the driver’s seat, didn’t say a word. You cast one last look at Mildred as you climbed in beside him. She was still standing there, watching you with that same soft smile, like she knew exactly what she’d stirred up.