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Good luck starting this puzzle.
You'll stop where you always do.
My middle is in the ending.
You can see on the outside that I skipped school,
but beneath that you'll find I'm deeper.

What am I?

Hints 1:

Your best shot is to start with my beginning and ending. Some users here have already identified those. "My middle is in the ending" probably won't make sense until you find my ending. If you strip away the parts of me that refer to skipping school, you'll find something that could mean the same thing as "deeper."

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  • 1
    $\begingroup$ Could do with some jurisdiction pointers :-( $\endgroup$ – Strawberry Oct 13 at 12:10
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    $\begingroup$ Typo in the hint: should be "your". $\endgroup$ – wizzwizz4 Oct 13 at 17:32
  • $\begingroup$ Thanks everyone for participating in my first puzzle here. All the feedback is helpful for future posts. $\endgroup$ – RaceYouAnytime Oct 14 at 19:58
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I think you may be

glowered - having stared angrily, as the title says.

Good luck starting this puzzle.

gl - good luck initials - found by PiIsNot3.

You'll stop where you always do.

red - the word ends in red, which is a traffic light stop.

My middle is in the ending.

owe means financially in the red.

You can see on the outside that I skipped school,

GED - General Educational Development is an alternative High school diploma. Credit PiIsNot3.

but beneath that you'll find I'm deeper.

lower - inside the GED.

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    $\begingroup$ Nice! This is my first puzzle on the site, hope you and others enjoyed it $\endgroup$ – RaceYouAnytime Oct 12 at 16:04
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    $\begingroup$ @RaceYouAnytime - I thought this question was great and hope you write more. Earlier answerers (before the hints) such as PiIsNot3 and JS1 deserve the credit for working through this puzzle. Also, Stiv and Avi's posts were excellent. $\endgroup$ – Tom Oct 12 at 16:21
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    $\begingroup$ the skipped school part is highly locale-dependent $\endgroup$ – njzk2 Oct 13 at 19:12
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Possibly, this riddle is a series of clues that results in the word:

GEOGRAPHY

My middle is in the ending.

This is the crucial line. If we look at the endings of each phrase in the riddle we find the letters EOGR just before the full stops. This will be the middle of our word...

You can see on the outside that I skipped school,

On the outside of this middle-word place GAP - since you 'skipped school' you were taking a gap year. We now have G-EOGR-AP.

but beneath that you'll find I'm deeper.

Beneath (i.e. at the end of) our word-in-progress we need a word meaning deep, i.e. high - or a homophone of sorts, HY. Altogether we now have GEOGRAPHY.

I can find no definition clue elsewhere in the riddle that this was the word we sought, but perhaps the challenge was just to find a word which could be constructed using the riddle...

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    $\begingroup$ This is great logic and I like it. Not the answer I'm looking for though. $\endgroup$ – RaceYouAnytime Oct 10 at 17:59
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    $\begingroup$ It is insane that this is not correct! $\endgroup$ – George Menoutis Oct 11 at 12:40
  • $\begingroup$ High is the opposite of deep. And if it's at the end, then "gap" isn't on the outside. $\endgroup$ – Acccumulation Oct 11 at 16:38
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Partial guess, but could you be

GLARE?

Couple of clues don’t really fit, but here’s my reasoning anyway:

Good luck starting this puzzle.

GL (good luck abbreviated) is the prefix.

You'll stop where you always do.

ARE is the suffix, and we have the phrase “stop where you are.”

My middle is in the ending.

Not sure about this one. Maybe the middle/infix is AR, which is a part of the suffix?

You can see on the outside that I skipped school,

The outer letters spell GE, which could stand for “general education.” In the US, you can “skip” high school by taking a GED (general education development) test. Probably too tenuous to be valid, though.

but beneath that you'll find I'm deeper.

No clue on this one at all. “Beneath” probably indicates the inner part, which is LAR, but I can’t find any connection between that and being deeper.

Title: Stare long enough and you will have found the answer

Glare is a synonym for stare, meaning fixating your gaze on something for a long time.

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  • $\begingroup$ This answer is getting a little bit closer $\endgroup$ – RaceYouAnytime Oct 11 at 14:43
  • $\begingroup$ Could the "middle" part be referring to the word "finale"? $\endgroup$ – Hugo Zink Oct 14 at 11:04
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Here are two guesses:

Guess 1: Having seen PilsNot3's guess, could it be:

GLAZED

Good luck starting this puzzle.

GL = Good Luck

You'll stop where you always do.

ZED = Last letter of the alphabet

My middle is in the ending.

A in Apocalypse

You can see on the outside that I skipped school,

GED = Alternative certification for those who skip high school

but beneath that you'll find I'm deeper.

AZ = Everything from A to Z?

Title: Stare long enough and you will have found the answer

If you stare long enough, your eyes will become glazed over.


Guess 2:

END

Good luck starting this puzzle.

You'd have to start at the end.

You'll stop where you always do.

You stop at the end, as always.

My middle is in the ending.

Actually the whole word is in "ending".

You can see on the outside that I skipped school,

ED is the notation for "unofficial drop" of a college course. For example, explained on this webpage.

but beneath that you'll find I'm deeper.

The deep end.

Stare long enough and you will have found the answer

The word "end" is in the riddle itself, in the word "ending"

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A partial answer because I cannot fit some of the clues, but could you be:

A magic eye puzzle?

Stare long enough and you will have found the answer

A magic eye puzzle is "solved" by staring at it until you see a 3D picture emerge.

My middle is in the ending

You have to cross/"diverge" your eyes in order to see the intended image.

You can see on the outside that I skipped school

A magic eye puzzle initially looks like random noise, or something completely unrelated.

but beneath that you will find that I am deeper.

Magic eyes are solved by looking "past" the image, rather than focusing directly on it.

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I think you are

GLABELLAR

Good luck starting this puzzle.

Abbreviated, "good luck" is GL

You'll stop where you always do.

From "Stop where you are!", the ending is AR

My middle is in the ending.

GL is followed by A, which is part of AR

You can see on the outside that I skipped school,

On the outside of A is how you know somebody skipped school - if the BELL hasn't rung yet

but beneath that you'll find I'm deeper.

GLABELLAR lines are vertical lines between the eyebrows, that appear when focusing or in deep thought

Title hint: Stare long enough and you will have found the answer

If you stare for too long, your focus may cause glabellar lines to appear between your eyebrows

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for example:

screen

because

I stare at you, you are a cover/guard/barrier, there can be a rear-view mirror in the middle of you, your outside is flat, you are flat (dull, dumb) because of skipping school, you are deeper beyond the flat surface (physical extension)

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1
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Perhaps a bit far-fetched, but I found this to be a reasonably good fit too:

sleep

Stare long enough and you will have found the answer

Eventually you'll fall asleep.

Good luck starting this puzzle.

You will always start this puzzle while being awake, the opposite of sleep.

You'll stop where you always do.

Sleep always stops when waking up, which usually happens in bed.

My middle is in the ending.

After you die (ending), you'll be in the middle of an eternal sleep. OR: Sleep usually occurs in repetitive cycles, governed by having one or multiple REM/awakening stages in the middle and at the end.

You can see on the outside that I skipped school,

If someone is sleeping during school hours, it is likely this person is skipping school. Furthermore, sleep is not condoned in school.

but beneath that you'll find I'm deeper.

A sleep or its dreams within can be conceived/perceived as deep.

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