The answer to 'Feeling described as "hoping for the best, but fearing the worst"' in the NYT Crossword is CAUTIOUSOPTIMISM — sixteen letters, the mindset of expecting good while bracing for bad.
Why CAUTIOUSOPTIMISM?
This is a quotation-style definition clue from a Saturday puzzle — the hardest day of the NYT week — and it works by describing a feeling so precisely that only one phrase fits. "Hoping for the best" is optimism; "fearing the worst" is the caution that tempers it. The compound noun for holding both at once is "cautious optimism," and in crosswordese the space disappears: CAUTIOUSOPTIMISM. It's the feeling of the job applicant who nailed the interview but won't celebrate until the offer letter arrives.
The answer is confirmed in the NYT Crossword of May 24, 2025 (Saturday, by Gene Louise De Vera), where it stretched across sixteen squares at 18-Across. Long quotation clues like this are a Saturday signature — they test whether you can convert a description into the exact idiom, and the letter count does half the work for you.
Solving Tip: Convert Descriptions Into Idioms
When a clue reads like a dictionary definition in quotation marks, your job is to name the phrase being described — not to paraphrase it. "Hoping for the best, but fearing the worst" isn't asking for your own words; it's pointing at an established idiom. Think of the standard phrases for mixed feelings (cautious optimism, guarded hope, tempered expectations) and test each against the letter count. Sixteen letters leaves exactly one candidate standing.
Saturday puzzles love this construction because it rewards precise vocabulary over trivia. If you practice converting descriptions to idioms — "fear of missing out" (FOMO), "hoping for the best but fearing the worst" (CAUTIOUSOPTIMISM) — these long across answers stop being walls and start being gifts.
Frequently Asked Questions
What is the answer to 'Feeling described as "hoping for the best, but fearing the worst"'?
CAUTIOUSOPTIMISM, with sixteen letters — optimism tempered by caution.
When did this clue appear in the NYT Crossword?
May 24, 2025, in the Saturday puzzle by Gene Louise De Vera.
Why is there no space in CAUTIOUSOPTIMISM?
Crossword answers never contain spaces — multi-word phrases are always entered as a single unbroken string.
Are long quotation clues common on Saturdays?
Yes — Saturday is the hardest NYT day, and long descriptive clues that resolve into exact idioms are one of its signature difficulty tools.