"Nah...all you gotta do is change your name to Tarzan and get a job at a strip club for dudes. Bet there's a lot of lonely old ladies who'd love to help you through college for a chance to snap your boxers." Dean tried to grin, keep a mostly encouraging expression, but he lost it pretty fast, unable to help the laugh that bubbled up. Sam definitely attracted the cougars at times.
"See! Health food, Sammy, I just like mine cooked." Dean nodded, smiling as he gave a little nod, turning up the music a little. He decided to fall quiet then, just listening to the music and letting Sam rest, trying to focus on the road instead of letting his thoughts wander too much.
When they made it to the bakery, Dean shut the impala off, glancing over at Sam before smiling to himself and trying to be quiet as he got out of the driver's side. He was fine with hopping in for pie, he doubted Sam cared too much about flavors since he wouldn't eat much more than a piece anyway.