It's odd, how sometimes he still wakes up thinking that everything is normal. The whole apocalypse was just some movie that he and the gang were going to see. The Leonardo and himself were getting ready to start their investigation about the old apartment complex on the outskirts of town. That he would walk into the messy office and see Worth and Lamont would be talking, joking around, alive. (It's not like Worth is not exactly dead but still, it was different.) Maybe he would even get invited to see Veser graduate.
The thoughts would sit comfortably in his mind until looked out the window to see whatever town they were in. Wonder about what he could help that with. Hear the the different stories about this place, how they survived. Realize how much like home it was. Before realizing that he would never get to see his for yet another time. He was never gonna walk those familiar streets leading to Conrad's apartment, or the Doctors office or even to his own home.
On those days that seemed to happen much more often then the really should, Leonardo would watch him concerned like any good protector would be. He would try to give him some sort of comfort. By stroking his arm or giving him an awkward hug.
Eventually he would get up and push thoughts into the back of his min. Mess with his ginger hair a bit, So he can put on his smiling facade. Before going into the remains of civilization to help them keep a home. To protect their family and friends, because he had done a shitty job taking care of his. He wasn't a hero, he was a failure.
Nobody could change his mind about that, and Nobody not even Leonardo would know that he felt this way.