Is it permitted for Catholics to pray for a specific sign as an answer to a question or dilemma they are experiencing in their life? For example, “Please let [such-and-so] happen as a sign to me that I should take this job.”
Yes, asking for a sign is permissible. Indeed, Archbishop Fulton Sheen counseled that the more specific the sign requested, the better. That said, this presumes that one does not treat the matter in a superstitious way (cf. CCC 2111). Signs are special favors from God, and may not be given even when requested. God usually reveals his will in less dramatic ways (e.g., through openness to correction or advice from mentors; through prudential consideration of pros and cons; through persistence in the sacraments, prayer, and meditation) and such ordinary means of discerning God’s will should never be superceded by a desire for signs and wonders. At its best, the gift of a sign is confirmation of the results of employing the ordinary means of discerning God’s will and is never a replacement for them.