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My friend told me the other day:

Robert ist einfach so sympathisch, den kann man nicht nicht mögen.

The entire sentence made sense

Robert is actually so nice, that you can't not like him.

However, when thinking about this sentence on the way home, I was wondering why my friend used "den" instead of "dass".

Robert ist einfach so sympathisch, dass man ihn nicht nicht mögen kann.

When he used the pronoun "den" I thought the sentence translated as

Robert is actually so nice, who you can't not like him.

Is that an accurate translation, or can "den" behave similarly to the english "that"? What purpose does "den" serve here from a grammatical perspective?

I would have thought "ihm" would have been the appropriate pronoun to use in this situation i.e. "him"

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Your observation is (partly) correct, den is the akkusative singular form of the demonstrative pronoun der and

Robert is actually so nice, that you can't not like him.

is not a literal translation of

Robert ist einfach so sympathisch, den kann man nicht nicht mögen

(But, since den is akkusative case, rather ihn than ihm is the corresponding personal pronoun - the latter would be dative case.) A somewhat literal translation into English would be

*Robert is actually so nice, him you can't not like.

(I think) there is no analogue construction in English, that's way all these attempts of a literal translation sound unidiomatic in English.

The construction is "conceptually oral", i.e. it would not be used in written conversation, but is fairly common in every-day-communication.

The translation your friend gave you keeps the meaning, but does not keep the grammatical structure:

Be aware that, contrary to the translated english sentence, the german sentence consists of two main clauses (Hauptsätze) here, and does not have a relative clause. den is not a relative pronoun, but a demonstrative pronoun and it is an object in the second main clause. That's why another proper translation into English would use just two main clauses:

Robert is actually so nice. You can't not like him.

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    Das »den« ist in diesem Fall ein Demonstrativpronomen.
    – Pollitzer
    Commented Apr 25, 2019 at 6:47
  • @Pollitzer Stimmt. Hab's geändert.
    – Jonathan Herrera ♦
    Commented Apr 25, 2019 at 6:53
  • I wonder how English expresses the distinction between ihn and den; him and that guy?
    – David Vogt
    Commented Apr 25, 2019 at 8:45
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    … not a relative clause … – I wished you had put this more prominently.
    – Janka
    Commented Apr 25, 2019 at 11:59
  • @Janka You are right. I used bold typeface now and added some paragraphing to emphasize this information.
    – Jonathan Herrera ♦
    Commented Apr 25, 2019 at 13:23

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