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Someone please help a baby Trekkie.

One should NEVER watch Enterprise first, because it has too many callbacks to the other shows that you won't understand without having the whole history of Trek in your head.
 
Nah, it just gives you an excuse to go back and watch the Ent episode again.

Or you could say that the other series' have callbacks to Enterprise!
 
Although personally, I think he should watch ENTERPRISE first, since, despite being made last, it takes place first.
That is of course, one way to see it, but, I think for a first time viewing, it's actually better to end with it, since Enterprise S4 I think is far more enjoyable when it expands on TOS races and episodes you already know. Additionally, I think the rewind to Enterprise at the end of the Spinoff Series works great as a lead in to the 2009 Movie, since Enterprise Canon occurred before the Movie 2009 Universe change, while all the Canon from the other Series has been shifted.

When I rewatch Enterprise and TOS in the near future, I will indeed be watching Enterprise first, to have the experience of seeing ENT S4 prior to TOS (Currently watching DS9, just finished S1 last night)
 
I would just go with series order based on when it premiered so

TOS
TNG
DSN
VOY
ENT

Whilst TNG/DSN over lapped by 2 season and DSN/VOY by 5 there wasn't much crossover between them.

DSN and TNG had a cross over in "Birthright" so perhaps you might ant to watch at least DSN's "Emissary" before then.
 
Although personally, I think he should watch ENTERPRISE first, since, despite being made last, it takes place first.
That is of course, one way to see it, but, I think for a first time viewing, it's actually better to end with it, since Enterprise S4 I think is far more enjoyable when it expands on TOS races and episodes you already know. Additionally, I think the rewind to Enterprise at the end of the Spinoff Series works great as a lead in to the 2009 Movie, since Enterprise Canon occurred before the Movie 2009 Universe change, while all the Canon from the other Series has been shifted.

When I rewatch Enterprise and TOS in the near future, I will indeed be watching Enterprise first, to have the experience of seeing ENT S4 prior to TOS (Currently watching DS9, just finished S1 last night)

Yep there is something to be said for both experiences though for first time viewing I would not be watching ENT first. I feel the same way about the Star Wars trilogies, they work differently depending on how you watch them.

I think it's quite a thrill to start with ENT and then later see Journey to Babel for instance.
 
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