Don't laugh at me but why am I just now realizing the significance of timing when Alan asks Charlie when is Jeff coming back to work??? Prior to Jeff working at the garage Alan really didn't have anyone to vent to and like we see when Jeff finds him working at one of Jeff's stations, work is his only outlet. Then after Jeff leaves we see he also uses a punching bag to relieve stress as well. But when Jeff was present we got these two instances:

Jeff letting Alan vent about not having enough money for the whole team. Then Jeff consoled him by reminding him if he was a bad boss no one would have stayed that long.

Then we see it again after a conversation with Dean in which Jeff helps him figure out a solution to the money problem. He even relents to Jeff that he had not, in fact, found a solution even though he was putting on airs for Dean.

So, after Jeff left he was back on his own with no one to talk to. And what happened right before talking to Charlie you ask? His argument with Dean left him upset and without his secretly caring mechanic.

Then Jeff comes back and we see yet another Dean fight (my boy was on the slow roll to psychopath early on) and who does he find solace in???