I've seen this a couple of times on tv shows and wondered if the dip is a little dish or if it goes straight into the hole in the bread? I've also seen it with clam chowder

straight into the bread. eat dip or chowder, then eat the bread. best if the stuff isn't particularly soupy and the bread is crusty.
You carve out the bread as much in one piece as you can. For a dip, you cut the carved pieces into large cubes to use for dipping. For soup or chili, you can save the carved stuff to use as bread crumps or croutons later.
Around these here parts, you can buy small, round loaves of sourdough French bread that are called "bread bowls" or "soup bowls." They are actually the perfect size for one or two people to have for dinner and not worry about leftover bread going stale.