That’s not the kind of question most high school seniors expect to find on their college admission applications. But it is one of the essay options that applicants to the University of Chicago face this year in their quest for a coveted freshman berth.

It is the kind of mind-stretching, offbeat or downright freaky essay question that is becoming more common these days as colleges and universities seek to pierce the fog of students’ traditional self-aggrandizing essays detailing their accomplishments and hardships.

From Caltech in the West to Wake Forest University in the East, more schools are serving up unusual essay prompts to gain better insights into young people’s minds and personalities. Colleges also hope for more authenticity in a process skewed by parental intrusion, paid coaching and plagiarism.

“It’s a way to see students who can think differently and go beyond their academic, intellectual and extracurricular comfort zones,” said Garrett Brinker, an admissions official at University of Chicago. Those essays also “break up the monotony of the application process,” for students and colleges.

The Common Application, the online site used by 488 colleges, offers such generic prompts as: “Discuss some issue of personal, local, national or international concern and its importance to you.” The site makes it easier for would-be students to apply, even if some are half-hearted about enrolling.

But an increasing number of schools prefer to hear only from serious applicants “aware of the values of the institution,” said Katy Murphy, president-elect of the National Assn. for College Admission Counseling.

So more colleges are adding online supplements that require head-scratching writing assignments. Examples include Tufts’ “Celebrate your nerdy side”; Wake Forest’s “Think of things that fascinated you when you were 10 years old — what has endured?”; Caltech’s “Please describe an unusual way in which you have fun”; and Brandeis’ “A package arrives at your door. After seeing the contents you know it’s going to be the best day of your life. What’s inside and how do you spend your day?”

For some students, the questions may lighten an otherwise burdensome task. But others are intimidated, said Murphy, who is college counseling director at Bellarmine College Preparatory, a high school in San Jose. “The colleges talk about the creativity of play and the philosophy of Plato. What the students are trying to figure out is: ‘What do the colleges want me to say?’ ”

Judy Rothman, author of “The Neurotic Parent’s Guide to College Admissions,” said schools like curveball essay questions because “they are sick and tired of reading the same thing over and over again” and because the topics encourage teen authorship without adult coaching.

High school seniors have mixed reactions, she said: “For a kid who is natural writer, it is relief and a great break from the tedious process of the applications. For the kids who just want to get through all their applications, it’s a nightmare because you can’t recycle material.”

Hannah Kohanzadeh, a Santa Monica High School senior, has embraced the trend. “So many schools don’t pay attention to the little quirks students have. Those personal things can tell whether a student belongs there or not,” she said. With deadlines two weeks away, she is finishing applications to Brandeis, Occidental and others.

For Occidental, an essay asked: “Identify and describe a personal habit or idiosyncrasy — of any nature — that helps define you.” She wrote about how she flaps her arms when she gets excited about hearing good music or reading a great book, and tied it to her love of new ideas. “I start flying,” she said.

For idiosyncrasies, other students described being so rushed that they brush their teeth in the shower, wearing certain underwear as a good luck charm for exams and falling in love too fast, according to Occidental’s Dean of Admission Sally Stone Richmond. Inviting such revelations helps ease applicants’ fears that they must appear perfect and is “an opportunity to seek candor in ways that won’t be intimidating to the student,” she said.

At Caltech, the question about having fun and others in a similar vein push applicants “to thoughtfully reflect and respond honestly about who they are,” said Jarrid Whitney, executive director of admissions and financial aid.

Now and then, an applicant reveals something “probably borderline unethical or demeaning to others,” Whitney said. For example a few years ago, someone wrote about spiking a teacher’s coffee with a potentially dangerous chemical. The teacher was warned in time, and the student did not meet academic standards for Caltech anyway. But if he had, that essay probably would have convinced officials he was “not a great fit in our community,” Whitney said.

University of Chicago, a pioneer in such essays, invites its students to propose topics for questions. A committee selects the winners. The optional “Where’s Waldo?” query this year has attracted much attention from fans of the picture books that send children searching for characters. “It is something that can go with a lot of different angles,” explained Brinker. Some essays recall growing up with the books, others invent Waldo adventures or make Waldo into a metaphor for world problems. One ambitious student created a treasure hunt, hiding a picture of the bespectacled Waldo in the campus library and providing hints to his whereabouts.

Sophie Salmore, a senior at Marlborough School in Los Angeles, tackled another Chicago question. It poses physicist Werner Heisenberg’s claim that “you cannot know both the position and momentum of an electron with total certainty” and asks for other concepts that cannot be known simultaneously. She wrote about embarkation and outcome and detailed her first roller-coaster ride and the school vegetable garden she established.

At first, she found the application daunting and almost skipped it. Then, she said, she realized it allowed her to be “more than test scores and GPA. I felt I could express myself.”

larry.gordon@latimes.com