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conundrum - A confusing and difficult problem, situation, or question, where there is no clear or easy solution.

Figuring out how to balance work and personal life is a common conundrum.

adjective

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arbitrary - Based on random choice or personal whim, rather than any reason or system

She felt that when the judges chose her competitor as winner of the debate, that the decision was totally arbitrary, and didn't recognize how well she had really done.

adjective

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convoluted - An explanation that is presented in a very complicated and difficult way.

The teacher's convoluted answer to the question showed either that he didn't understand the subject, or that he didn't know how to explain things clearly.

noun

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dilemma - A situation in which a difficult choice has to be made between two or more alternatives, especially equally undesirable ones

Life is filed with dilemmas, often leading to no good outcome.

adjective

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oblivious - Not aware of or not concerned about what is happening around one

Alan was oblivious of the person talking to him because he was staring at his phone.

adjective

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perplexing - Confusing and difficult to understand

Scientists find it perplexing how life's incredible complexity came out Earth's hot water all by itself.

noun

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controversy - A prolonged public disagreement or heated discussion about something important.

The athlete was surrounded by controversy after the doping allegations.

verb

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digress - To temporarily leave the main subject of a conversation or discussion

Please don’t digress—we need to focus on the main issue during these important negotiations.