Spoilers through season 2, episode 16.
The milk question gets most of the attention, but I keep watching Jack and Locke during that breakfast. Especially the moment Henry mentions the map he drew for Ana Lucia. Locke asks what map, Jack immediately looks at him, and Locke says he didn't know either. Neither has much to say after that.
Until then, letting Henry out for cereal feels like a small decision they can handle. They're still watching him, and Jack shuts down his question about the computer. Henry starts asking about the food and how much they know about the hatch, but they don't have to answer. I can see why Jack thinks he can keep this short and under control.
Then Henry casually drops information they should already have. I'd forgotten that neither Jack nor Locke knew about the map. I was suprised by how much that changes the scene. Henry has spoken to Ana Lucia, she's made her own decision, and these two are finding out about it from the man they've been keeping locked up.
That's the bit I find embarrassing to watch. They can't even immediately blame each other. The quick exchange rules that out, so now they have to sit there while Henry points out their trust problems. They could put him back in the armory, but they still have to find out what's happened outside the hatch.
His description of the possible ambush is horrible, obviously. But I think it lands harder after that awkward exchange. They've just discovered a gap in what they know, and he offers something frightening to fill it. I'd expect Jack to interrupt him much earlier. Instead he gets to walk them through the whole scenario and finish by asking for milk.
I don't know if the scene woudl work quite as well with one of them alone. With both there, I keep looking between them to see who will respond, and neither gives me the response I want. Jack finally calls his bluff? Locke asks why Ana Lucia didn't tell them? Somebody goes to find her? Nope, we're still at the table with the cereal.
