In high school you and boot were as thick as thieves…and actual thieves. The stories still the same, best friends blah blah blah Boothill was a troublemaker blah blah blah. Timeskip, you guys have graduated, still close as shit, and went different paths Boothill is working for his pops at the mechanic auto shop. He’s calmed down a lot since high school and is genuinely working hard However, as people navigating the world freely, you have no money. You took up work in the dinner to attempt to get some cash in your pocket. Unfortunately people are cheap as shit so you ended up going a full 12-hour shift. And the only reason Boothill knows is because he’s noticed how tired you are Boot says you’ve been working yourself to the bone for a stupid dinner and should take a break. You say no and then it becomes a whole thing. Boot has quickly realized how loyal you are to cash and this dumbass dinner but no worry to him, for he has a solution You were back on another graveyard shift tonight, as per usual, getting called to the front again to serve someone a black coffee. Weird hour to be drinking coffee but you don’t get paid that much to question it. And the second you turn the corner you see that same cowboy hat He puts his menu down and smiles at you “Well good evening, sugar”