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As per the question: the word I'm looking for is used to describe something that only one who (for want of a better way of putting it) went through something can understand that thing.

To make the question a bit less ambiguous: I went to my parents' house and they were watching a comedy which exaggerated the absurdities of the education system of Socialist eastern/central European countries during the 60s/70s. They found it hilarious because they had experienced this education system for themselves. I was scratching my head and frowning because I was brought up in a Western society in the 90s.

Consequently, my parents were watching a/an X comedy (what is X)? The word I'm not looking for is niche.

EDIT: as per below suggestions. The word should also fit the context (continuing from the above example) "I therefore find my parents' culture to be very X." The word is neither "relatable" nor "alienating" since my parents couldn't be watching an alienating comedy, but it is also not true that my parents' culture is relatable.

Perhaps it is possible that the word I'm looking for does not exist.

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    Not a single word, but the expression "you had to be there" is pretty common. – Leo Adberg Mar 18 '19 at 3:31
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    Some would use "relatable" to fill that blank. Apparently, "relatable comedy" is a thing, I don't get it, of course, but that's because I am not going through what it mocks. pinterest.com/sunygcc/relatable-comedy-for-college-students/… – remarkl Mar 18 '19 at 4:13
  • "Relatable" works in this context, but I'm looking for a broader word. A second example of where this word could fit is in the sentence: "I flew to a country overseas, and they had some strange habits there. It is probably because I find their culture to be very X (i.e. I didn't understand it because some context and prior knowledge was missed to me)." Relatable wouldn't fit here. Alienating isn't quite it either, since you're appreciating you can't understand something and therefore don't feel hostility or anxiety toward the subject. – R. Rengold Mar 18 '19 at 4:52
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    @R.Rengold I don't think it's possible for the same word to satisfy both of the example sentences you've provided. Despite that, I would still edit your question to make your example sentences (add the second one from your comment) completely obvious: (1) My parents were watching a very ___ comedy. (2) I find their culture to be very ___. Note that I changed your first sentence slightly. Otherwise, it would require a noun, while the second sentence would require an adjective. (Alternatively, you can change your second sentence so that a noun fits it.) – Jason Bassford Mar 18 '19 at 6:12
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You are right to say it would be difficult to find a single word to cover all cases, and in some cult related cases we may use concepts such as exclusory, sectarian (religious), parochial (locality but still religion), cliquish (clannish) and for disputes there is factional

But the only one near to differencing a generation / cultural gap is

"generational"
means relating to a particular generation, or to the relationship between particular generations. Thus the best I can suggest is

(1) My parents were watching a very generational comedy.
(2) I find their culture to be very generational.

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People from older generations tend to have a different take on things.

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I'd suggest insider. Your parents had insider knowledge. In your sample sentence you could use quotation marks to indicate an analogy to the 'insider joke' (or 'inside joke').

From Dictionary

Insider
noun a person who is a member of a group, organization, society, etc. a person belonging to a limited circle of persons who understand the actual facts in a situation or share private knowledge:
Insiders knew that the president would veto the bill.

My parents were watching an 'insider' comedy

or more natural:

The comedy was for insiders/full of insider jokes.

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generational

adjective

  • relating to or characteristic of all the people born and living at about the same time, regarded collectively.

  • relating to the different generations of a particular family.

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