At the very least Alt World Bobby isn't their Bobby and Sam will never ask Ruby to consider him family. Sometimes though Sam still sees pieces of his deceased father figure in Alt Bobby that catch him off guard.

It's all he could ever ask of her to open up in bits and pieces. He'll worry she's bottling the experience up otherwise. They can talk about what Eileen has to do with what Astaroth put in her head as well. They should talk about it as he's fairly clueless certain he already set Eileen straight.

Car shopping would be exactly the kind of excuse the two of them need to have a breather and make it a date.

The rest of the ride is fairly silent. Sam makes a faint effort to smile when Dean drops it and focuses on Ruby the rest of the time. He drifts sleep for minutes at a time and when they stop to gas up, he doesn't exactly feel hungry to ask for anything when Dean heads inside to pay. He looks mildly surprised but accepts the food Dean brings back with a thank you. Dean knows exactly what he would have asked for with the Greek Yogurt and the mixed nuts. Back at the bunker, Sam helps Ruby to their room, aware Dean has the rest handled. He shuts the door so the demon ward going back up might be felt by Ruby a little less. He stays with Ruby a while and slips out for food again when his stomach starts to feel hunger pangs.

The first place he looks is in the kitchen for Dean. Before he can even consider making himself food, he realizes he should get his hand better tended to and in working order again. "Hey, did Cas call back yet?" Apparently, as neither of them are aware, Castiel is having that much of a hot date.