As I said in the "gnomes" thread, all the races in my homebrew have a theme. With halflings, the theme is "freedom".
They're generally athletic folk, a little more prone to wanderlust than some, but they know they'll always be welcomed home. Halfling families wouldn't dream of keeping a restless youngster at home. In the countryside, halflings are more typically herdsmen than farmers; they don't generally have a green thumb, but they do wonders with their riding dogs and a flock of tsula (fleece like a sheep, milk like a goat, rather stupid in an unpredictable way). Many halflings travel in caravans as merchants or performers; the go more for acrobatic feats than narrative performance. City halflings often go in for jobs requiring their clever fingers, such as crafting, scribing, locksmithing, and (not as often as people think) thievery and pickpocketing.
Halflings get their rogueish reputation partially through misunderstandings. They regard confinement as horrible. Halfling communities have no jails; they punishe their miscreants through unpleasant work, banishment, or outright death. Since they view confinement as torture, they will at times try to "liberate" criminals from jail. If the criminal's crime was terrible enough, they may proceed to kill him, but they would view it as "setting justice back on its path". Halfings take violent crime very seriously in their communities, but tend to ignore playful theft as long as nothing someone really needs is stolen. The typical halfling etiquette for getting your "missing" belongings back is to steal them right back, plus a little extra for the sake of your reputation. If not, inquiries around town generally result in missing belongings reappearing in unusual places; for example, strapped to the underside of a tsu-la.
Part of their reputation, though, they come by honestly (or not). Halflings hate to see objects of value "going to waste". The average halfling wouldn't think of stealing the healing artifact from the Pauper's Temple, but a cache of fine jewels just sitting in some rich man's box isn't doing anyone any good, is it? He wouldn't even miss them.
Because of their small size, many halflings are especially sympathetic to children of all types...it comes from having a permanent child's-eye view of the world. They tend to be a little protective of young creatures of any race, sometimes to the point of being a bit silly about it: "But we can't kill the green wyrmling! It's a baby!" They can be impulsive, especially if they think they need to escape a potentially confining situation. They're huge believers in free will. They're very reluctant to consult their gods directly, believing that a god's decision closes off future choices. Instead, they tend to pray for spirit-touched dreams that give them an inkling of their god's possible wishes. Halflings think the idea of "fate" is ridiculous. After all, why would a god put them there if he/she/it already knew what was going to happen?
Halflings get along well with neutral or good-aligned orcs, humans, and the less book-seeped gnomes. They find dwarves stodgy and boring, and get tired quickly of the many layers of civility in elven society.
