# Why can't a nucleophile attack the intermediate of an electrophilic aromatic substitution?

During an electrophilic aromatic substitution, the aromatic pi cloud interacts with an electrophile to form an arenium ion (AKA sigma-complex). The following image (from my organic chemistry class) suggests that aromaticity is always restored and that a nucleophile can't interact with the resonanced carbocation of the arenium ion.

If I were to replace the base in the above image with a nucleophile that is an extremely poor base (such as iodine), could the nonaromatic cyclodiene be formed? Or would the reaction just halt instead?

Follow up question: If electrophilic aromatic subsitution doesn't work, how would one go about making the cyclodiene (with Nu and E substituents) from an arene? Is it possible?

As for another nucleophile to attack the $\sigma$ complex, the positive charge is delocalized and deprotonation step is much faster. I think that it would be easier for the base to extract proton than to attack the Delocalized positive charge. The proton already has a $\delta$+ charge due to Hyperconjugation effect. I think that even if the base if a strong acid, it can dissociate to give H+ but the non-aromatic intermediate will not remain the solution as it is.
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