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I don't recall if this was a standalone book or a book series and I don't recall any of the characters' names at all. I read this book 6+ years ago and I only remember these details:

  • The main character (a guy) was transported to another fantasy world. Somewhere along the way there was also another girl in the story who was also transported to the same world as him.
  • There was some scene in the beginning of the book where the guy and his friends were talking about what girls they liked (before he was transported to another world).
  • The guy had to answer three questions/riddles at some point. One of the questions was something along the lines of "What is the longest one syllable word that exists?" and he answered with the word "strengths".
  • Someone was tortured at some point but I don't recall if it was the MC or a side character.

I'm not even completely sure if all of these details come from the same book/book series or not, but the most distinct detail I recall is definitely the riddle one.

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A World Without Heroes by Brandon Mull. Book one of his Beyonders series.

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Jason Walker has often wished his life could be a bit less predictable--until a routine day at the zoo ends with Jason suddenly transporting from the hippo tank to a place unlike anything he's ever seen. In the past, the people of Lyrian welcomed visitors from the Beyond, but attitudes have changed since the wizard emperor Maldor rose to power. The brave resistors who opposed the emperor have been bought off or broken, leaving a realm where fear and suspicion prevail.

In his search for a way home, Jason meets Rachel, who was also mysteriously drawn to Lyrian from our world. With the help of a few scattered rebels, Jason and Rachel become entangled in a quest to piece together the word of power that can destroy the emperor, and learn that their best hope to find a way home will be to save this world without heroes.

It was published in 2011 so it fits the time you remember reading it. The guy is Jason and the girl is Rachel. The scene with the three riddles is:

“Your final question, Lord Jason,” the regent said.

Jason felt a compulsion to ask, How much wood would a woodchuck chuck if a woodchuck could chuck wood? He resisted and looked down at his paper. Question three is your chance to use the best of what you prepared. Hopefully, question two made winning less urgent!

Jason sucked in his breath through his teeth. After reading the first two questions he had not expected to have to supply one of his own. His mind raced. Probably the best question he had come up with was an odd piece of trivia he had discussed one day with a kid named Steve Vaughn in his English class. The six letters in Steve’s last name had inspired the conversation.

“What is the longest one-syllable word you can think of?” Jason asked Copernum.

“Is that the entire question?” the regent confirmed.

“It is.”

A third hourglass was overturned.

“Point of clarification,” Copernum said, brow creased. “Are you asking me to name the monosyllabic word containing the most letters?”

“I’ll allow the inquiry,” the regent said.

“I am,” said Jason.

The chancellor stroked his chin, squinting up at the ceiling, as if lost in profound calculations. He folded and unfolded his arms. He rubbed his brow. Jason crossed his toes for luck. It appeared the chancellor had never considered this question, which meant he had a chance. Ever since the conversation with Steve, Jason had noticed whenever he came across a long one-syllable word. The word he had in mind, if not the longest, was pretty close. The chancellor stared darkly at the floor. Then he looked up, leering.

“I have your answer. How dare you pose such an absurd riddle? The longest monosyllabic word I can think of is thoughts. Eight letters.”

All eyes shifted to Jason. He straightened. “Apparently, Chancellor, one-syllable words are not one of your strengths. Nine letters.”

Several characters are tortured at various points in the story. You are possibly remembering chapter 24 where Jason is put in a cell and a venomous snake is put into the cell with him. After fighting off the snake for several hours Jason is finally bitten, and it turns out the snake's venom is a truth serum. Jason is interrogated while he's under the influence of the venom.

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