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Well, since it seems that my other riddle won't be solved any time soon, here's a new riddle.

Stuck in this prison for what seems forever,
How long do I have left? 10 years? 20 years? Never?

Over the years, you've stuck to this same ritual.
Only, instead of purpose, it's mostly habitual.

Look to where you rest to find what I am.

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12 Answers 12

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Perhaps

a desk?

Stuck in this prison for what seems forever,

Students are often stuck in desks K-12, then higher learning

How long do I have left? 10 years? 20 years? Never?

Once you start working, it is often while sitting at a desk

Over the years, you've stuck to this same ritual.

Again, school, then work.

Only, instead of purpose, it's mostly habitual.

Often required

Look to where you rest to find what I am.

Where you sit, hence rest.

And the title, You come to me day after day. I see you in a most unflattering way.

Well.. a desk sees your butt (school desk) all day, which might be considered unflattering for the desk..

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  • $\begingroup$ This is what I was looking for, though my reasoning was slightly different. for example, rot13(Zbfg fghqragf fvg ng gur fnzr qrfx rirel qnl qrfcvgr abg orvat sbeprq gb. Nyfb, sebz gur qrfx'f cbvag bs ivrj, vg'f frrf lbhe ohgg nyy qnl ybat.) $\endgroup$ Sep 21, 2018 at 22:39
  • $\begingroup$ @Joe-You-Know, rot13(Nuu, gung'f ba cne jvgu jung V jnf guvaxvat jura V fgngrq vg'f 'hasynggrevat sbe gur qrfx'.) Thanks for the clarification! $\endgroup$
    – T James
    Sep 21, 2018 at 22:46
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You may be

A mirror or my own reflection

Stuck in this prison for what seems forever,

How long do I have left? 10 years? 20 years? Never?

My reflection seems as if it is trapped in the mirror while I roam outside in the real world.

Over the years, you've stuck to this same ritual.

Only, instead of purpose, its mostly habitual.

It has become our daily habit to look at ourselves in the mirror to check if we look good or we have dressed properly or not. Even when we aren't going anywhere we always stop by the mirror at least once.

Look to to where you rest to find what I am.

Most people have a mirror by their bedside. It can be the dressing table mirror or a full length one.

Finally the title, You come to me day after day. I see you in a most unflattering way

The mirror shows you for how you actually look. Even when you aren't dressed properly or when you just wake up with your hair all messy, the mirror will show you exactly how you look without any flattery.

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  • $\begingroup$ An interesting answer, but like I said with QuantumTwinkie, the hidden clue would suggest this isn't quite it. $\endgroup$ Sep 21, 2018 at 16:18
  • $\begingroup$ Yes I see that acrostic but it makes no sense to me. Quantum may have just guessed it. $\endgroup$
    – R.D
    Sep 21, 2018 at 16:19
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Are you

A toilet

You come to me day after day. I see you in a most unflattering way

We go to the bathroom everyday, if it had eyes it would not be a flattering angle for sure

Stuck in this prison for what seems forever,

Toilets are in prison cells (bit of a reach i know)

Over the years, you've stuck to this same ritual.

We never stop going

Only, instead of purpose, it's mostly habitual.

Its a thing of nature, we do it because we have to

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  • $\begingroup$ Darn I see while typing my answer someone else beat me to it!! $\endgroup$ Sep 21, 2018 at 18:57
  • $\begingroup$ We were close together, but I guess i beat you to the punch! $\endgroup$
    – Cubemaster
    Sep 21, 2018 at 19:05
  • $\begingroup$ Still, you might have better reasoning than me. All up to the digression of the OP $\endgroup$
    – Cubemaster
    Sep 21, 2018 at 19:06
  • $\begingroup$ +1 and nice answer! Welcome to Puzzling.SE. Why not take the tour for an easy badge? $\endgroup$
    – Chowzen
    Sep 21, 2018 at 20:21
  • $\begingroup$ This answer was so close. It's what I thought most people would go for at first. $\endgroup$ Sep 21, 2018 at 22:37
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Is it

School

Stuck in this prison for what seems forever,

K-12

How long do I have left? 10 years? 20 years? Never?

You will always learn.

Over the years, you've stuck to this same ritual.

Wake-up, Bus-stop, Learn, Homework

Only, instead of purpose, its mostly habitual.

You need to go to school?

Look to where you rest to find what I am.

?

Hidden hint

The acrostic spells Shool or School with no c.

Title

The school system knows what you get wrong and what you are bad at.

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    $\begingroup$ As indicated by the last line, it's not this, but it is related. Also, I can't believe I messed up the acrostic that badly. :P That was not intentional. Oh well, can't really change that without changing the entire riddle. $\endgroup$ Sep 21, 2018 at 16:24
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    $\begingroup$ Also, the title is important. $\endgroup$ Sep 21, 2018 at 16:25
  • $\begingroup$ @Joe-You-Know, did I mention anything similar in my answer? :) $\endgroup$ Sep 21, 2018 at 16:27
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    $\begingroup$ I'd suggest you think smaller, also it's a literal thing/object. $\endgroup$ Sep 21, 2018 at 16:28
  • $\begingroup$ Hmmm, could it have anything to do with rot13(N fragrapr yvxr n cevfba fragrapr?) @Joe-You-Know $\endgroup$ Sep 21, 2018 at 16:51
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Are you

A Yearbook

You come to me day after day i see you in a most unflattering way

Yearbook photos are ugly

Stuck in this prison for what seems forever,

Pictures are in yearbooks forever

How long do I have left?

Yearbooks tell us when we will graduate

Only, instead of purpose, it's mostly habitual.

We mostly buy yearbooks out of habit

Acrostic Hint:

Yearbooks are from schools

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  • $\begingroup$ This is a good guess, but not what I was looking for. $\endgroup$ Sep 21, 2018 at 22:36
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Are you

Bedtime

Stuck in this prison for what seems forever,

You will always have to go to bed.

How long do I have left? 10 years? 20 years? Never?

You need a bedtime forever.

Over the years, you've stuck to this same ritual.

Go to bed, sleep, wake up.

Only, instead of purpose, its mostly habitual.

You gain a sleep schedule that your mind wants to follow.

Look to to where you rest to find what I am.

Your bed.

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  • $\begingroup$ Heh heh, I like this answer, though the hidden clue would most certainly show that this is not the answer I'm looking for. $\endgroup$ Sep 21, 2018 at 16:16
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Alright, bear with me here.

Are you

The bathroom/toilet?

Stuck in this prison for what seems forever, How long do I have left? 10 years? 20 years? Never?

Sometimes, you are stuck in the bathroom for a while. Because... you know.. reasons.

Over the years, you've stuck to this same ritual. Only, instead of purpose, it's mostly habitual.

Many people go to the bathroom at the same times every single day, if only because it fits their schedule, not that they really need it.

Look to where you rest to find what I am.

Sometimes, the bathroom is the only place you can catch a break and be all alone. In other words, it is great for being truly at rest.

Title:

I would dare say that the toilet's view of you is not terribly flattering

Acrostic hint:

Spells "SHOOL", but from comments I imagine it was meant to say "School". Students go to the bathroom to get out of class daily.

Seems like a long shot to me, but what the hell, let's go for it.

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  • $\begingroup$ This answer was so close. It's what I thought most people would go for at first. $\endgroup$ Sep 21, 2018 at 22:38
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You are a

Burned-out teacher

Stuck in this prison for what seems forever, How long do I have left? 10 years? 20 years? Never?

Counting down the days till retirement

Over the years, you've stuck to this same ritual. Only, instead of purpose, it's mostly habitual.

Teaching the same classes, with the same lesson plan

Look to where you rest to find what I am.

Honestly not quite sure about this one, you rest at your desk at the head of the classroom? Or maybe the teacher's lounge?

And the acrostic almost spells

School, which is where teachers work.

You come to me day after day. I see you in a most unflattering way

A burned-out teacher would have less-than-flattering impressions of their students.

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  • $\begingroup$ Nice, not quite what I imagined but good guess. $\endgroup$ Sep 21, 2018 at 22:40
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Is it a

A shower/bathtub

Stuck in this prison for what seems forever,

Bathtub/showers are fixed

How long do I have left? 10 years? 20 years? Never?

They last a while usually

Over the years, you've stuck to this same ritual. Only, instead of purpose, it's mostly habitual.

Have a bath everyday?

Look to where you rest to find what I am

In the restroom?

Title

Yes, a very unflattering view

Acrostic

Showers after school gym?

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  • $\begingroup$ I'd say this serves a very good purpose, but I like this answer. $\endgroup$ Sep 21, 2018 at 23:00
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I think you're a

Coffin

Stuck in this prison for what seems forever

Yeah, you can't get out of a coffin

How long do I have left? 10 years? 20 years? Never?

Probably never

Over the years, you've stuck to this same ritual

Only, instead of purpose, it's mostly habitual

Not really sure about this one, but I think that a dead person inside a coffin just sleeps forever (like it's a daily ritual without purpose)

Look to where you rest to find what I am

Coffins are known as final resting places

Title :

Actually, people visit their loved ones' graves every once in a while

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Are you a

Bed

Stuck in this prison for what seems forever,

You will always go to sleep Obligatory XKCD

How long do I have left? 10 years? 20 years? Never?

You will always need to sleep throughout your life

Over the years, you've stuck to this same ritual.

You go to bed, sleep and then wake up again

Only, instead of purpose, it's mostly habitual.

Your body clock likes to follow a common schedule

Look to where you rest to find what I am.

Oddly enough, you often rest when you sleep(!)

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My best guess:

the prison could be a wrapper, the "never" suggests something seldom used, but "ritual" implies repetition, birthdays. Where you rest is "bed" or perhaps a chapel of rest .. could be a candle in a box.

I also thought of:

Initially I was thinking toilet roll! because I thought it could be a fudged acrostic for "spool"; other thoughts include "music" because of bars forming a prison and the mention of "rest".

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