Out of some combination of deep emotional investment in the task and an ambient desire to impress the extremely cool immortal witch-knight, he's exactly as careful as he would have been without backup, or maybe even moreso. Hob pads softly between the tents in the dark, avoiding the wandering eyes of people who might think him a ghost, much like - well, like a ghost. (Soldiering as a profession only gets you so far, between wars. He has been a thief, too, in this first life.)

In a few minutes, as promised, he returns, looking very pleased with himself. He is holding the described rock lovingly to his chest with one hand, and spinning a dagger between the fingers of the other. 

"Have to track down your own things often, or just in the habit of doing very kind favors for new friends?" he wonders.

"Let us say the latter. What is passed around tends to return, in my experience."

What an incredible sort of person to be. Hob wants to be her when he is a thousand. "I'll keep that in mind."

"Now then. I believe you mentioned getting a drink?"

"I would be delighted." They shouldn't need to go terribly far to find one; where there are armies, there are opportunists selling alcohol. It might be rather harder, though, if she has anything resembling standards.

It's still the aftermath of a battle. Standards are negotiable for a while.

Excellent. Then drinks they shall have. 

Hob tucks away the knife as soon as he's sure all his fingers are working correctly, but keeps holding the rock. He almost lost it and now he's kind of nervous to let it out of his hand, much less his sight.

"Keepsake of someone?" Kassandra asks.

Wistful smile. "Yeah. My little sister. Used to love to bring me random stuff she found in the woods. Mostly frogs, actually, but those are a bit harder to keep in your pocket for decades." 

"Mm. I had a sister like that. She was more into snails, though. Liked to feed them to Ikaros."

"Aww," charmed giggle. Now delightedly imagining two small children in a pile of frogs and snails. Possibly throwing them at each other. "Ikaros is - was? - a ... dog?"

"My eagle."

Ah yes. Witch familiar. That's normal and fine.

"Oh! Goodness. What's it like having an eagle? I've seen hunting hawks," from a considerable distance, "but those're... smaller."

"You know, I'm not entirely sure how to answer that. I've never not had Ikaros. He watches my back, he scouts. He is my friend and companion."

"Huh. Sounds lovely, that."

"Makes the long years more bearable."

"Makes sense! Though I have every hope that I will not find them to require bearing at all, myself."

His broad grin says he absolutely knows he is tempting fate. It's worked out great for him so far, after all.

"I hope you can keep that attitude up."

"I'm sure going to try. Come say hi again next time you're in my neck of the woods and you can find out how I do at it, eh?"

"I shall look forward to it, Hob Gadling."

"Likewise."

And in the meantime he's happy to hold her attention before she goes as long as is reasonable. Or slightly unreasonable, really, they're immortal and have all the time in the world. If she has any stories she'd care to tell of Constantinople or suchlike he will be the world's most interested and attentive active listener.

(Plausibly deniable admiring gazing aside, he is determinedly not flirting, though. In his available cultural vocabulary, to do so would be to imply insulting things about her class and/or gender that he absolutely does not believe or care to imply.)

She has a great many stories, of palaces and walls and monuments, ships and merchant caravans, trackless deserts, lush valleys, forbidding mountains, vast steppes, icy wastelands. Emperors and queens and herders and farmers and blacksmiths and potters and mercenaries and guardsmen. Rivers she's swum in and cliffs she's climbed, fortresses she's assaulted and damsels she's rescued. Enough stories to carry the night through into the next day, if he can stay awake so long.

He is enthralled, and will with grest enthusiasm stay up, occasionally shaking himself, literally until he loses consciousness against his will.

Unfortunately, thanks to the war and the nearly dying this morning and all that, he last slept properly about two weeks ago - for that matter he slept at all more than forty hours ago - and he will, in fact, lose consciousness against his will around midnight, mumbling something vaguely apologetic on his way to faceplanting on the table.

Fair enough. (Wonder if he'll ever get the trick of staying awake for arbitrary periods, or if that's just a her thing.)

Kassandra will cart him over to her tent and dump him on the cot to sleep. No reason to let the fellow be rolled again.

When Hob awakens, she'll be sitting on the ground out front, sharing a few strips of jerky with the large golden-brown eagle perched on her shoulder.

Zzzzz coze warm zzzzzz wait what the fuck.

Hob hasn't slept in anything even loosely resembling a bed for months, and was fully expecting to wake up having been tossed unceremoniously into a muddy corner and/or ditch by the barkeep after Kassandra left. This would not be an uncommon experience and he has survived it just fine before. (... wait, has he? ...yeah, that happened to him like twice a week in his early twenties, well before any meetings with mysterious dark strangers, he probably survived it in a nonmagical way.)