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I'm planning on running a Zoom trivia tournament with monetary prizes and am trying to avoid any concern about cheating to preserve competitive integrity. What are some types of questions that are more-or-less "cheat-proof?" (that is, they can't trivially be Googled within the time-limit... about 4.5 minutes)

Examples I have come across in the past which I think are good contenders (looking for examples that are not in these categories):

  • Picture Round: Identify pictures of either famous religious sites, national treasures, natural structures or icons from pop culture, scenes from movies.
  • Audio clips of songs which contestants must identify the name of

Edit: A few more examples I came across:

  • One way to have audio-based clues that avoid the the Shazam problem. Reverse the song.

  • Leave out the easiest search term from the question. For example, "How old is Etta Place when she leaves for Bolivia?", without ever mentioning Butch Cassidy and the Sundance Kid by name. This tip was suggested by Ken Jennings on his blog in 2006.

For bonus points: One of the rounds needs to be multiple choice. How do you make a relatively cheat-proof multiple choice question?

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    $\begingroup$ This question seems to be fairly vague - simply fishing for a "big list" of possible ideas. No answer could possibly be the definitive answer. $\endgroup$ – bobble Nov 17 '20 at 16:20
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    $\begingroup$ Nowadays most phones do music clip recognition completely automatically, you don't even have to touch the phone as it displays the song name on the lock screen. Questions that are still (as of 2020) relatively computer-proof (but still easy to construct) might include some kind of wordplay or riddle. For the multiple choice, odd-one-out seems like an ideal format. $\endgroup$ – Bass Nov 17 '20 at 16:30
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    $\begingroup$ @Parseltongue, if you're looking for which answer gets the most votes, then that's a popularity contest, not a question fit for our Q&A system. $\endgroup$ – bobble Nov 17 '20 at 16:38
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    $\begingroup$ For the close-voters: This is an example of the rare "relevant, on-topic question that doesn't fit the Stack Exchange format". When this happens, we would do well to realise that the fault lies in the site design, not the question. After all, it is the good questions that are important; the guidelines and rules are only tools for making good questions more frequent. $\endgroup$ – Bass Nov 17 '20 at 16:45
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    $\begingroup$ @Bass, I think music clip recognition still only works on the exact popular sound track not on any other version of the same music. So I think it should work fine with for example non-professional covers (even when you take them from say youtube). This can be a fun twist that you have to recognize the song despite it being a non-professional cover. $\endgroup$ – Kvothe Nov 18 '20 at 16:21

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Here are some things you could try:

Rebus
A rebus is a puzzle device that combines the use of illustrated pictures with individual letters to depict words and/or phrases. You can draw the pictures on Paint or something similar but a popular device I've seen recently is to use emojis to represent TV shows, movies, songs, etc.
For example the following is a TV show

🎀 🎃 🐎 👨

Wordsearch
I don't think this needs much explanation but you could present a wordsearch and ask competitors to find a number of words. It's a little tricky to give the answer for an arbitrary wordsearch but if you set up a grid reference and provide a way for players to specify the direction of the word (e.g, using cardinal directions) then you can make it work.

Cryptic Clues
You could specify that all answers in a particular round come from a specific category and then give a cryptic clue which must be solved to give the answer. For example, if the category is Premier League Football stadia, then you could give the clue

Expel to back room (4,4)

Perhaps to make it more difficult, you can skip enumerations and make the categories more broad (as it's not hard to google all the Premier League stadia).

Estimation Questions
As long as you're not afraid to do some calculations beforehand, you can ask teams to estimate answers. Sometimes this can be tricky even with Google. For example,

I wish to build a square pyramid out of standard toilet rolls purchased from Tesco (local supermarket) and build it to equal the height of the world's tallest building. How many toilet rolls do I need?

or even

How much would it cost?

Then you can either give teams a point for being within a certain range or you could tie this in with multiple choice.

Odd One Out
This is also a good category for multiple choice and you can purposefully make it difficult to Google. For example, can you guess the odd one out from these options

COS, SIN, HBP, DH, SS

Personal Questions

This is also something you could tie in with multiple choice. For example,

How old am I in days?

This will be hard for the team to Google but maybe they could make reasonable guesses based on how well they know you (maybe not a great category if the quiz goes beyond friends and family).

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    $\begingroup$ This is a fantastic set of ideas. Thank you so much. $\endgroup$ – Parseltongue Nov 17 '20 at 16:25
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    $\begingroup$ I object to your "odd one out" example. The last item should be PS. :-) $\endgroup$ – Gareth McCaughan Nov 17 '20 at 20:04
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    $\begingroup$ Note that googling the Odd One Out example took me less than 30s --well within the allotted 4:30-- and I'm not very familiar with the subject matter. Conversely, guessing the meaning of emojis is nearly impossible for me. The point is that you might end up with something that tests different skills than a traditional trivia challenge. (For better or for worse) $\endgroup$ – ikegami Nov 18 '20 at 5:42
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    $\begingroup$ Good answer but funny fact: I just googled “How many days since [my birthdate]” and got an answer immediately. $\endgroup$ – Damila Nov 18 '20 at 6:34
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    $\begingroup$ Without intending to brag, I got the odd-one-out in under 5 seconds by googling the whole set - Google helpfully put "Missing: SIN" under the first result, giving me the answer directly :-) $\endgroup$ – lxop Nov 19 '20 at 5:04
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My friends and I did quizzes for about four months, and these are my favourite rounds we did that fit your criteria:

Bad film reviews
There are aggregated lists of film reviews that are baffling and terrible - read your friends the review, and have them guess which movie it's for.

Q: Why is he wearing jeans in the ocean? - 1 star
A: Aquaman

Specific picture rounds
Its easy to reverse-search an image now, but if you get creative you can make it impossible.

Each picture is a closeup of a chocolate bar wrapper - name each bar!

(As a bonus we were asked what my friend's favourite chocolate bar was based on the images - the letters on the wrappers spelled out the name of a seventh bar, but only a couple of us got it because we were so focused on recognising the wrappers)

Who is that?
Similar yet different to the picture round above, get your friends to guess who is in the picture but make it difficult - obscure background characters in TV shows, celebrity yearbook photos (or even photos of yourselves as teenagers)

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    $\begingroup$ "Bad film reviews" is gold! $\endgroup$ – Wainage Nov 18 '20 at 20:30
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    $\begingroup$ If they're real reviews, they might show up in Google searches though. $\endgroup$ – ConMan Nov 19 '20 at 3:44
  • $\begingroup$ @ConMan true, I was thinking it could work with the constraint of 'can't be trivially googled in the time limit' since the quizzers would have to remember the exact wording of each review or try to write them down as fast as possible, it depends how fast they can Google I suppose haha $\endgroup$ – Tonks Nov 19 '20 at 8:31
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    $\begingroup$ I think the point of the "bad review" is to have a hilariously unhelpful description of something such that it is 1) not immediately obvious which film it refers to and 2) does not refer to more than one film (or film series). While you might find an example that satisfies 1 and 2 "in the wild", it may be easier to design something yourselves. 2 in particular can be tricky to satisfy if you're not intending it (which is the case for a real review). $\endgroup$ – Discrete lizard Nov 19 '20 at 10:03
  • $\begingroup$ @Discretelizard that's all good points; part of the fun for me was that they were real reviews, but if you have the time then made up ones work too. For instance 'too many cats' was left as a review for Cats and had the quizzers doubting themselves that anyone would really do that! $\endgroup$ – Tonks Nov 19 '20 at 15:45
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You will never be absolutely sure that no one cheated, but when I've done these, I made the prizes to not have enough monetary value to bother. Like top prize was a $25 amazon certificate. Big enough to make it interesting, not big enough to be ruthless. I state the rules up front -- no electronics, no Google, using the honor system. If you're worried about this, you're wasting valuable time that you could use to write good clues, which will be your main drawing point. It's more important to have an interesting and entertaining game, then to have to be a policeman. Somewhat OT: A couple of hints on good clue writing, in case this is your first time:

  1. Avoid static questions and answers, particularly avoid answers which are just dates or numbers. "What year was the Magna Carta?" Boring!

  2. Mimic Jeopardy, where most clues have more than one path to get to the answer. Example: "Which "colorful" character in the game of Clue might get a letter from Nathaniel Hawthorne?" Here we intimate that the answer is a color, and refer to the book The Scarlet Letter which, of course, points to Miss Scarlet. This also makes it harder to look up, as might require looking up both characters in the Game of Clue, and works by Nathaniel Hawthorne.

  3. Don't overestimate your audiences ability. Throw in enough easy clues so that even the poorest player will have some points. Nothing worse than a trivia game where no one gets the answers.

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  • $\begingroup$ State the rules and include some question, not answerable without google help - helps to spot cheaters :) $\endgroup$ – Arvo Nov 18 '20 at 15:10
  • $\begingroup$ I think you may underestimate the competitive nature of some people. People will cheat just to get a piece of paper that says they came in first place. limeade.com/en/press/want-to-cheat-your-fitbit-wsj $\endgroup$ – user3067860 Nov 19 '20 at 20:39
  • $\begingroup$ @3067860 I don't doubt that people will cheat just for cheating's sake, but people will want to play your game because it's entertaining and enjoyable, not because you've absolutely eradicated all chances of cheating. If your questions are motivated by fear of abuse, you aren't putting enough effort into good gameplay. It's hard enough to write really good entertaining clues that stimulate user's love of puzzling without restrictions. $\endgroup$ – Owen Hartnett Nov 22 '20 at 5:04
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One strategy would be to allow Google searches. Then write questions that you need to know trivia to know what search terms to use.

Or let them solve that problem for you. Have them write the questions. If you want to avoid them just writing ridiculously hard questions, you can have a Dixit-style scoring system.

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While you can't use any of the ones that have already spread online, you can take inspiration from memes/hashtags like "Describe a film poorly" since a lot of the fun of the meme is in avoiding any of the words that would normally appear in an explanation of the plot. But if you can make up your own, then you can put forward clues like "Nostalgia trip leads to rocky reunion" that they won't be able to Google.

Similarly, you could draw inspiration from the show Only Connect where most of the rounds involve trying to find the common thread between disparate clues and either explaining the link or offering the next item in a sequence. Often, there's a level of abstraction, obfuscation or misdirection involved - for example, a sequence of book titles might only use the last word, or they might use pictures of a pile of shovels, a structure over a river, a bottle of liquor and a tool for stoking a fire to hint towards popular card games (Spades, Bridge, Gin and Poker).

The big two warnings for making clues like this are (1) they involve a fair amount of creativity and effort on your part to create, and (2) they need to walk a fine line between being not immediately obvious, but where there is little room for dispute as to the correctness of the answer. Also, it assumes your audience is up to the challenge, as these kinds of clues tend to be much harder to answer than normal trivia and often require a fair amount of mental gymnastics.

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A fundamental issue with hosting a 'trivia' contest online, is that when players have the ability to search the internet for answers, information being obscure isn't enough for it to make a good question. Also, typing into Google isn't the only issue you're facing - the two examples provided in the question can be cheated through reverse image search and the Shazam app respectively.

One option to help with the cheating issue is to use an online quiz platform such as Kahoot!. A key factor is that this allows you to introduce time pressure that would be difficult for a single human to coordinate directly within Zoom. Players who already know an answer, or guess correctly, have a distinct advantage. This also helps any issues of bias about whether a player got their answer in on time, as it doesn't come down to human judgment.

Here are some ideas for constructing questions that are difficult to cheat on using the internet:

  • Obscure TV show and movie quotes. It can still be from a popular TV show or movie, but a lot of dialogue can be memorable without showing up easily in searches. This is easy to test yourself, though it could still be a little time consuming to come up with interesting and fair questions. It may help to have some idea of what movies the participants are likely to have seen. This could work well as a multiple choice question.

  • Obfuscate some key words of a regular trivia question. For instance, using only the first initial of a person's name, or broadening a place name to the state or country it's in, or use some form of code such as Pig Latin. You could also substitute names for descriptions. This usually makes it harder to search.

  • Fill in the blanks. This also offers you the opportunity to hid some of the most searchable words.

  • Rapidfire questions. Basically, deliver a larger number of 'easy' trivia questions, to be answered in a short space of time, and the challenge is in who can answer the most questions correctly in a given space of time. This is a type of question where ideally, google searching anything will only slow you down. This could work well with multiple choice questions.

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REVERSE TRIVIA

You provide an answer to trivia question, and ask your participant "What is the question for this answer?"

You can tune the obscurity of the 'answer' so that participants can come up with the questions. To limit possible (and perhaps correct, but unintended) questions, you can narrow down by category, year, or other hints. I find it not easy enough to google up. It might work in your online use-case.

For reference, you can see this video.

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One way to make searching basically Google-proof is what my parents (teachers) did with their tests: Don't ask for a piece of information, ask for combining two pieces of information.

(They weren't doing this to Google-proof, but to test understanding. Their questions normally involved applying facts to concepts. If you forgot the fact part you could look it up {open book/open note}, but if you didn't understand the concept that wasn't going to do you any good.)

Edit: Since an illustration has been requested. This was almost 40 years ago but there's one of his questions that somewhat sticks in my mind. It's actually a poor question as I was pretty sure of the answer without knowing the tribe in question:

True/False: You are studying [tribe whose name I do not recall--the key point being that they are a stone age culture in New Guinea]. You submit the following expense list, is there anything, anything at all that will be questioned on it?

[Item I do not recall at all]
[Item I do not recall at all]
[Food, \$xxxx]
[Van, \$11,000]

If you forget what tribe it was you can look it up (remember, open book/open note), but if you don't understand what a stone age culture is like you won't realize how utterly useless a van is in a jungle with nothing more than foot paths.

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    $\begingroup$ Could you provide an example of how combining two pieces of information would work? Perhaps an example problem that would require it? $\endgroup$ – bobble Nov 19 '20 at 23:30
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I think the answer is obvious: give clues that aren’t easily searched because they are neither textual nor clean digital files.

Examples: (1) name this tune - that you just whistle - Shazam can’t help with that, or (2) what team did this person play for - with a photo you hold up on a printed sheet in front of the web cam - reverse image search can’t help with that, or (3) what is this ancient symbol - that you draw by hand on a piece of paper. Etc.

Even harder if you compound the clues: for the film with this theme song (whistle it), the main actor received an Oscar for just one other film - what was the last letter of that film’s title?

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Missing link type of questions. e.g. three people, places, films etc... hard to get a quick answer from a web search.

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    $\begingroup$ Could you expand this answer with an explanation of what a "missing link type question" is? Perhaps some examples? $\endgroup$ – bobble Nov 19 '20 at 19:38
  • $\begingroup$ Like these:funtrivia.com/playquiz/quiz2515581ccd2d8.html $\endgroup$ – AlexJ Nov 20 '20 at 23:42
  • $\begingroup$ And... funtrivia.com/playquiz/quiz503585c6a58.html $\endgroup$ – AlexJ Nov 20 '20 at 23:44
  • $\begingroup$ Please edit your answer add this information, and don't include just links - quote the relevant sections that you are pulling examples from. Answers should be in answers, not comments. A bare link is not much use, as it could go dead at any time, and we want answers to be entirely self-contained. $\endgroup$ – bobble Nov 20 '20 at 23:49
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Mine https://www.reddit.com/r/dadjokes/ for clever wordplay. Unless you use the phrases verbatim, it's practically impossible to Google.

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