Italian · Pronunciation Guide
or-goh-LYOH-zoh, with the stress on the third syllable. In IPA: /or.ɡoʎ.ˈʎo.zo/. The tricky part is right in the middle: that "gli" is a single consonant sound, not a g followed by an l.
Written as four syllables, or-go-glio-so, and Italian keeps all four distinct, though the "glio" syllable is really just one consonant (the palatal "gli" sound) plus a vowel, not two separate consonant sounds the spelling suggests.
Listen: orgoglioso
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The letters "gli" are Italian's way of writing a single sound that doesn't exist in English: a palatal lateral, made by pressing the middle of the tongue against the roof of the mouth. It's close to the "lli" buried inside the English word "million," but squeezed into one consonant instead of two.
Sono orgoglioso di te.
I'm proud of you.
Listen: Sono orgoglioso di te.
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"Orgoglioso" agrees with the person it describes, so "Sono orgoglioso di te" is what a man says; a woman would say "Sono orgogliosa di te." As with "innamorato," the feeling is expressed with "di" (of) rather than a word that maps onto English "of" or "for" — you're proud OF someone, and that preposition is fixed, not a free choice.
The word covers the same range as English "proud," from genuine warmth ("I'm proud of you") to the more negative sense of someone being arrogant or full of themselves, so tone of voice and context do the work of telling the two apart.
English readers seeing "gli" almost always default to one of two wrong sounds: either a hard g followed by a distinct l (making it sound like "orgoglee-oh-so," close to the English word "glory"), or they drop the g entirely and just say an l. Neither is right — the whole point of "gli" is that it's one sound, not a sequence, and it's made in a completely different part of the mouth than either an English g or l.
The second trap is the "-oso" ending. Because it's the cognate of English "-ous" (as in "curious," "famous"), English speakers tend to import the English pattern and swallow it into a quick, unstressed "-us." In Italian, "-oso" is fully pronounced with a clear, closed "oh" and an audible voiced z — it never gets reduced.