So my friend writes in an email: どうしてかって？ A reasonably innocuous statement, except I’m not exactly sure which verb かって is. So I consult my trusty dictionary:

欠く (かく) (v5k) to lack; to break; to crack; to chip; (P);
書く (かく) (v5k) to write; (P);
掻く (かく) (v5k) (1) (uk) to scratch; (2) to perspire; (3) to shovel; to paddle; (P);
描く (かく) (v5k) to draw; to paint; to sketch; to depict; to describe;
且つ (かつ) (adv,conj) yet; and;
勝つ (かつ) (v5t) to win; to gain victory; (P);
刈る (かる) (v5r) to cut (hair); to mow (grass); to harvest; to clip; to shear; to reap; to trim; to prune; (P);
苅る (かる) (v5r) to mow;
駆る (かる) (v5r) to drive (car); to spur on; to impel; (P);
借る (かる) (v5r) to borrow; to have a loan; to hire; to rent; to buy on credit;
狩る (かる) (v5r) to hunt;
支う (かう) (v5u) to support or prop up;
飼う (かう) (v5u) to keep; to raise; to feed; (P);
買う (かう) (v5u) to buy; (P);
勝手 (かって) (adj-na,n) kitchen; one’s own convenience; one’s way; selfishness; (P);
曾て (かって) (adv) (1) once; before; formerly; ever; former; ex-; (2) never (with negative verb);

Keerist! Sure, I should be able to figure out from context which one of the sixteen possibilities is the right one, but I don’t know if I have the energy to even read through the whole damned list to find out. Next time I’m learning Spanish!