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In the first Matrix, Trinity advises Neo not to go down a particular road. Here's the quote:

Switch : Our way, or the highway.

Neo : Fine.

Trinity : Please, Neo. You have to trust me.

Neo : Why?

Trinity : Because you have been down there, Neo. You know that road. You know exactly where it ends. And I know that's not where you want to be.

Does this "road" have any special meaning in Matrix, for example for being especially dangerous, or is "road" rather figurative there? Excuse me if this question tends to be subjective, but I wanted to know if this particular road has any references or special meaning in the Matrix series since I am not sure if I know all the background, for example from the video games.

Here's a Youtube link to this fragment:

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A metaphor? In The Matrix? That’s unpossible! – Paul D. Waite Mar 23 '14 at 23:26
The trick is not to assume that EVERYTHING is a metaphor here. – d33tah Mar 23 '14 at 23:29
This is a very good first question. In light of the sequels, it may refer to previous Ones. I am unsure how much the Wachowski's had fleshed out their mythos by then. – James Sheridan Mar 24 '14 at 4:02
@d33tah: well indeed. Sometimes when there is no spoon, there literally is no spoon. – Paul D. Waite Mar 24 '14 at 9:45
@d33tah - It's certainly a common figure of speech. I do agree that we can endlessly parse the script for hidden meaning but in this case it's actually quite a solid question. – Valorum Mar 24 '14 at 11:23
up vote 24 down vote accepted

She's being both literal and figurative.

Literally: The road does lead back to the Matrix. They've travelled outside the "Core Network" into an area of the matrix that is sufficiently far away that they can hack into it and generate an Exit. If Neo goes back down the road he'll find himself back in an area with a far greater level of machine control and oversight. Although Neo doesn't know it (yet) Trinity is warning him that that's not where he wants to be if he wants to find out what The Matrix is.

Figuratively: She's warning him that the easy road is the wrong road. He must dare to walk the 'road less travelled' in order to prove himself worthy of joining them in knowing the truth about The Matrix. She's also not-so-subtly reminding him about his recent encounter with the Agents (after refusing to obey Morpheus) and quite how well that worked out for him.

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Any source for saying that where they were in the Matrix was less under the control of the machines than anywhere else in the Matrix? – Xantec Mar 23 '14 at 22:18
Less oversight, certainly. In 'reloaded' Morpheus says "We're inside the core network" where there seems to be fewer hardlines and greater agent activity. – Valorum Mar 23 '14 at 22:23

That's actually an old saying. It means being disappointed in how things have been. Doing the same old things in the same old places will just lead to the same old feelings of being dissatisfied with the inevitable and expected results. "You've been down that road before." You already have experience there.

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Although a long shot, she might heeding her mentor's advice and passing it on to the newcomer:

From the Reloaded script:

Trinity: You always told me to stay off the freeway.
Morpheus: Yes, that's true.
Trinity: You said it was suicide.

You asked for the significance of roads and this is where it pops up again in the Matrix. One might argue, that the first instance where we hear a reference to "choose the right path" (in the first film) is the instance, where Neo starts following Morpheus' teachings, while not doing so before (remember the office). At the same time, the instance where we again are told about a road Morpheus himself says:

Morpheus: Then let us hope that I was wrong.

And indeed, from this point forward we find more and more that Morpheus himself was misled and Neo has to emancipate himself from his mentor.

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It's certainly an interesting interpretation. I always viewed the freeway comment more literally. It's dangerous and there's basically no escape. – Valorum Mar 24 '14 at 14:10
@Richard: Think about it; in the beginning, we are led to believe that Morpheus is always in control and in the know about what is going on (even when ambushed in the old building, he stays in control of the situation!). He is the wise master -- never wrong. Given that they survive the freeway, the notion of "Then let us hope that I was wrong" is validated and really marks the first crack in Morpheus' reputation, eventually culminating in complete devastation when Neo tells him about the nature of the prophesy. – bitmask Mar 24 '14 at 16:32
Prior to Neo's arrival it's clear that the Freeway was a deathtrap. They only survived because SuperNeo made a ridiculously well-timed arrival – Valorum Mar 24 '14 at 22:49

Actually she is referring to when Neo did not what he was told to (in the previous scene where he didn't obeyed Morpheus and the agents got him). So the road being showewd in that take actually has nothing to do with the phrase Trinity says.

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Welcome to SFF:SE. What makes you certain that the road Neo and Trinity are both looking at has nothing to do with her statement? Of course, part of her statement is figurative. But why are you certain that nothing is literal? You can make a more convincing case if you provide sources. – Praxis Mar 4 at 16:50
@praxis - Not least because they're looking at an actual road when she says it. – Valorum Mar 4 at 17:21
@Richard : Indeed. (I agree 100% with your accepted answer.) – Praxis Mar 4 at 17:25

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