It's true that Wing doesn't get the reference, but he assume it has some hidden meaning and takes it for what it's worth.

Gunmax was a complicated mech, one Wing was only just starting to understand. But like he was with Drift before, Wing is patient, used to mechs needing to lash out and willing to listen.

"Sometimes it seems like being numb would be easier." It probably goes without saying. But the message is clear, that at least Wing understands what it means to lose someone.