The answer is CAUTIOUS OPTIMISM — a 16-letter phrase that appeared as 18-Across in the May 24, 2025 Saturday NYT Crossword by Gene Louise De Vera.
Why CAUTIOUS OPTIMISM?
The clue is a textbook definition clue: it describes the feeling in plain words, and the answer names it. Cautious optimism is exactly the mindset of hoping for the best while fearing the worst — expecting a good outcome but staying braced for a bad one. The phrase is so precisely matched to the clue that once you see it, the long answer practically fills itself in.
Saturday puzzles are the second-hardest of the week, and long 16-letter answers like this one are often the grid’s anchors. A smart solving strategy: when a long clue reads like a dictionary definition, trust the most literal phrase that fits the letter count.
A Clever Cross-Reference in the Same Puzzle
The May 24, 2025 puzzle even winked at this answer. Its 54-Across clue read: “Positive result of having 18-Across, perhaps” — and the answer was PLEASANT SURPRISE. In other words, if you’re cautiously optimistic, a good outcome feels like a pleasant surprise. Constructors love these little thematic echoes, and spotting them can confirm a shaky long answer.
What Does Cautious Optimism Mean?
Beyond crosswords, cautious optimism is a widely used term in business, economics, and everyday life. Analysts describe markets with “cautious optimism” when indicators look positive but risks remain. It’s the measured middle ground between blind hope and outright pessimism — optimism with a seatbelt on.
Frequently Asked Questions
What is the answer to “Feeling described as ‘hoping for the best, but fearing the worst'”?
CAUTIOUS OPTIMISM (16 letters).
When did this clue appear in the NYT Crossword?
May 24, 2025 (Saturday), constructed by Gene Louise De Vera, as 18-Across.
How many letters is the answer?
16 letters: CAUTIOUSOPTIMISM.
What was the related 54-Across clue in the same puzzle?
“Positive result of having 18-Across, perhaps” — PLEASANT SURPRISE.