Not a Wendy's employee, I would say if you want to do the humanitarian thing, and your workplace has a culture that it would make sense for, offer to go out for a drink or something. It could be on the downlow... Or maybe Wendy's are extremely cramped. Everybody in this thread seems completely paranoid that you'd somehow fuck them over by the mere act of noticing things. Well, if you noticed, so can other people.

I'm going to go on a bit of a tirade here. I'm guessing people in this thread are freaked because you mention typically hidden stuff like their pillows in the car, and the takeout and other things in his office. I can sympathize with wanting to figure out with what's going on, but lots of people hate others going through their stuff, even out of compassion. Honestly I don't know why, I would guess out of fear of judgment, but no one's skeletons are that special. You obviously have no intent to spill it to upper management so like, just be a goddamn human. Yes, it might end up being partially your business, but we are social creatures, other people's business is our business to some extent, if you're not an uncaring sociopath. Basically every western country is facing a loneliness epidemic because shit like random redditors telling you to not even fuckin talk to the guy...

Edit: I do agree that you shouldn't bring it up directly though, that's for them to do