Pining!Dean has been a thing before Cas was even around. Having a parallel to a canon relationship makes the symbolism of it in connection with Cas even more wonderful. In 3x02 Dean drops Sam off at the motel and they pause on this huge sign! Where do we see Dean next? Lisa’s doorstep. Pine symbolism = longing.
Edited to add: Dean was very eager to get to Lisa. At the end of the episode it wasn't necessarily about her (she was a bendy weekend almost a decade ago) but it ended with Dean longingly looking at Ben in a fatherly way, even confessing to Lisa that he wishes he could have what they have: each other, a home, a normal life. He was longing for the whole kit-n-kaboodle. With Cas, he longs solely FOR CAS.









