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In the opening scene, Tony Stark said this to peter Parker in car.

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Don't do anything I would do, and don't do anything I wouldn't do. There's a little gray area in there. That's where you operate.

What exactly does the bolded part mean?

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    It means that Spider-man shouldn't do the things that Tony does, neither should he do the things Tony wouldn't do – Edlothiad Oct 4 '17 at 8:03
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    Don’t be an Avenger, and don’t be a bad guy. Maybe do a little bit of good stuff that isn’t quite big enough for the Avengers to bother with, but mainly, don’t get yourself hurt, because then I would feel exceedingly guilty. – Paul D. Waite Oct 4 '17 at 8:04
  • I don't understand the close vote - this question seems perfectly on-topic to me. – Gallifreyan Oct 7 '17 at 16:32
  • @PaulD.Waite Also the grey area on the other side, he is acting outside the law (I don't think he's registered under the Sokovia Accords, or Aunt May would've probably found out through that somehow), but he's not a bad guy either. – Izkata Oct 8 '17 at 5:30
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    @PaulD.Waite I don't recall it mentioned onscreen a lot, but one of the major plotlines for the first half of Season 4 involved a hate group that used the registration to find Inhumans to hunt down. After that was the Agents of Hydra event, which took place almost entirely in a virtual world with an altered history. – Izkata Oct 8 '17 at 17:06
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It's the somewhat tired joke of someone saying the standard phrase of "Don't do anything I wouldn't do" (implying that they should be on good behavior) only to realize that that doesn't cover much, generally followed by "Never mind. Don't do anything I would do," except that Tony is self-aware enough that he starts with saying to not follow his example, and then thinks to add to not do things that he wouldn't consider doing (which is assumed to be really bad things rather than being responsible).

It's a joke.

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    Not even a warning for that TVTropes link. You live dangerously young Boots – Edlothiad Oct 4 '17 at 11:06
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    I thought about it, but I already had a parenthetical. Besides which, people need to learn to mouse over links before clicking. Sometimes you don't learn until you burn your fingers. :-D – FuzzyBoots Oct 4 '17 at 11:07
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Remember that this is set after Civil War() in the MCU (indeed, you kinda need to watch it before this one for some of the context). The main premise of that movie was the tension between Stark (who believed that the Avengers should always be accountable to governments) and Captain America (who believed they should not).

Stark is being his flippant-yet-serious self here. Old Tony (circa Iron Man 1 and 2) never cared about the rules. New Tony (post-Civil War) has to care about the rules (because he kinda went to war with his friends over it), but he also had to admit that Captain America was also right in that there's a limit to how much following the rules can go.

You could rewrite what he's saying as

You need to follow the rules. Except when you shouldn't

Stark's way of putting it is just for comedic value.

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