Ask one clear question and the chart for that moment answers it, by the rules astrologers have used for centuries: the planet for you, the planet for the matter, and whether the two meet before either changes sign.
The chart is cast for the moment and place you ask (Placidus houses; traditional horary often uses Regiomontanus, which mostly moves the intermediate cusps). You are the traditional ruler of the rising sign, with the Moon as your co-significator; the matter is the traditional ruler of the sign on the cusp of its house. The answer is yes when the two planets reach an exact major aspect before either leaves its sign (a conjunction directly, a sextile or trine easily, a square or opposition with effort), found by stepping the real planet positions forward to the minute. Failing that, the Moon can carry the light from one to the other (translation), or apply to the matter itself. Classic cautions are checked first: a rising degree under 3 or over 27, the Moon void of course, the Moon in the Via Combusta, Saturn in the 7th. Ask once and mean it; the tradition says a question asked again and again blurs the answer.