It was probably just a matter of time before things went haywire, as they tended to do. That's normally enough to make Tim play it safe. A long line of nameless faces meant the feelings aspect never has to come into play. It's not just meant to protect himself. It's more about not subjecting anyone else to all this damage.

Damage that not even Raylan fully knows the extent of. The vicious cycle of trauma and drinking and nightmares. Some are harder to come back from than others. Some feel impossible to pull himself out of until he does. None of them are something he wants other people around for.

But this -- Raylan's crooked smile and the hand gripping his hip, everything highlighted in an early morning post-sex glow. He's thought about it too much to willingly let it go now that he has it within reach. Even if it means selfishly breaking a few of his own rules.

Maybe it'll end in disaster, but maybe it'll be as worth it as the broken furniture.

"What if I said tonight?"

Is it greedy? Almost certainly. Does he care? Definitely not.