"We did, yeah." The smile was definitely an older brother who had a lot of fun in ways that simply weren't for parents' and possibly little brothers' ears. Sam knew the smile, so Dean didn't have to explain.
He drove them to the park near a particular burrito stand that he was more than a little fond of. He didn't order a burrito right away. No, he just sat in the car and waited.
When he got the call, he smiled again, but it wasn't the earlier one. No, this was a proud almost 'told you so' smile because Jen had been there for him. He knew he could count on her.
"That burrito stand I like." He'd taken her there at least once. "I'll get you one for your troubles. I'll even throw in one for your ginger dick..." He winced. "That didn't sound like I thought it would." He didn't wait for her to confirm, just hung up, and swatted Sam's shoulder before getting out of the car. Yes, Sam would have to get out too.
The older Winchester got in line and waited for it to move and for Jen to show up with the head exploding information.