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Il collega con il quale discuto il progetto è intelligente.

Il collega con il quale discuto il progetto è intelligente.
The colleague with whom I discuss the project is intelligent.
From Lesson 173:Relative pronouns with prepositions (il quale, la quale)·Italian

Questions & Answers about Il collega con il quale discuto il progetto è intelligente.

Could I just say con cui instead of con il quale in this sentence?
Yes! Con cui and con il quale both mean "with whom" and are completely interchangeable here. Using il quale (and its variations) is simply a bit more formal and has the added feature of explicitly showing the gender and number of the person you are referring to.
How do I know whether to use il quale, la quale, i quali, or le quali here?
The relative pronoun must match the gender and number of the noun it refers back to. Here, it refers to il collega (the colleague). Since il collega is masculine and singular in this sentence, you must use il quale.
Wait, why is it il collega? Doesn't the -a ending make it a feminine word?
Collega is one of those tricky nouns that can be either masculine or feminine depending on the person it refers to, but the spelling stays the same in the singular. We know this is a male colleague because it uses the masculine article il. A female colleague would be la collega, which would then change the relative pronoun to con la quale.
I learned that "to discuss" is discutere di. Why is it just discuto il progetto without di here?
Discutere can be used both directly with an object (discutere il progetto) or with the preposition di (discutere del progetto). Using it directly is often a bit more formal and emphasizes examining the project itself, but both are grammatically correct and very common.
If this sentence were about a female colleague, would intelligente change to intelligenta?
No, it would stay exactly the same. Adjectives that end in -e in their singular form (like intelligente, grande, forte) do not change for gender. They are the exact same for both masculine and feminine nouns.

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