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Look for examples of Technology and Society Marching On, Aluminum Christmas Trees, and scenes that would resemble Mister Sandman Sequences if they occurred in an period piece.
Compare with Two Decades Behind, which is when something inadvertently feels like a period piece despite having been made a good time after the period it seems to be based on, and We're Still Relevant, Dammit!
Such a scene would have been made at the time with the focus entirely on Cold War politics, but the first thing the modern audience notices are the clunky cell phone and the mullet. Zeerust is when a work's depiction of the becomes dated, so all works with a far-future setting belong there, not here.
While just about every work becomes somewhat of a period piece after it becomes more than a decade old due to the characters referencing old trends, wearing out of style fashions and using out of date technology, this trope only really applies to works that wear their dates so blatantly that a viewer can identify the era or even year it was made in as soon as they begin to watch it.
For example, while the 1990s sitcoms dated due to the rapidly-changing nature of what's considered "hip".
Some jokes fall victim to this, when a history lesson is essentially required to explain the joke to folks who weren't around at the time the joke was funny.
(Being completely overtaken by events by time of airing, and being called "instantly dated" by the press, have both qualified in the past.) For most works, it won't be particularly clear which ones really do bleed their production date out of every pore until roughly a decade has passed.
Important Sidenote: To avoid questionable examples, do not add a work less than 10 years old unless the situation is especially unusual.
May overlap with All Love Is Unrequited and Gayngst. Of course, some characters can simply resort to Jumping the Gender Barrier or perhaps, if they're desperate enough, resort to Genderbending.
Compare to Settled for Gay, where they may have incompatible orientations, but they decided they probably wouldn't find a suitable suitor anyways.
If, somehow, the work manages to feel just as relevant today as it did then, if not more so, it's an example of Values Resonance, not this trope.
Obviously films and TV shows done in black and white, or non-high definition, as well as video games, will automatically be dated for technology reasons, but if we listed them all we'd be here all day.
, for when long-running series make blatant (and sometimes forced) references to modern culture in an attempt to seem up-to-date or to look more "hip", often resulting in one of these.