Learn Italian: Potresti chiedere uno sconto al grossista? - Could you ask the wholesaler for a discount?

In English, you ask "for" something. In Italian, chiedere takes a direct object, meaning you directly ask the thing itself. Adding per here is a very common mistake for English speakers.

Why do we use al grossista instead of dal grossista (from the wholesaler)?

English speakers usually ask for something "from" someone. In Italian, the fixed structure is chiedere qualcosa a qualcuno (literally: to ask something to someone). This relies on the preposition a, which combines with il to form al.

The word grossista ends in "-a". Why does it take the masculine article in al?

Nouns ending in -ista (which often indicate professions) can be masculine or feminine depending on the person. Because we see al (a + il), we know this specific wholesaler is a man. A female wholesaler would be alla grossista.

Why use the conditional potresti instead of the present tense puoi?

Just like in English, using the conditional potresti (could you) rather than the present puoi (can you) makes your request softer and more polite. It is the most natural way to ask for a favor in Italian.