Tommy:
He hates it... solely stemmed by jealousy. As a kid he didn't care that his parents spoke only in English to him, that they felt as if they should immigrate fully by dropping their Italian roots and acting as if they are Americans.
Which means now he feels an annoyance his parents didn't speak Italian to him so he could understand half of the people in the building. So when he found out you also speak fluent Italian his face was just -_- and decided he will go pick up a book from the library after this.
Paulie:
His Italian isn't the best. Very rusty, also because he has the mindset of "We are in America, why should we speak Italian?!" but at the same time he's annoyed his Italian has worsened from lack of use as now he can't keep up with everyone else.
He has told you to speak Italian more. This makes it able for him to pick it back up as now he can only understand you by relearning what words you are saying. So many times he holds his hand up to halt you, a deep frown, groaning: "I know that word. I know... What was that fucking word?!"
Sam:
He's a capo, of course he speaks fluent Italian! He converses in Italian with many of the men and the don. It's fun to speak in his mother's tongue, brings a sort of comfort. So if you can speak it too he is glad.
Both will speak a mix of English and Italian when together. It happens without either even realizing until someone points it out. Sometimes an English word just comes quicker to mind or an Italian word is easier and quicker to say.
Vito:
Italian got spoken in his home even after coming to America. So first half of his childhood was mixing Italian and English while speaking to his sister, or even others outside.
If you begin speaking Italian he can easily engage in it. It means when Joe visits he has to not laugh as he will have to witness Vito and you having a conversation that starts in English, shifts to Italian, then back to English with some random words changed out for their Italian.
Joe:
He picked up words here and there, mainly the bad and funny ones. He can follow a conversation if spoken slow and simple, mostly with the help of context as well. So conversations with him are basic things or the dumbest conversations with him snickering like a kid hearing a naughty word.
He picks up words quick though, so give it time and keep talking Italian and soon he will become intermediate level.
Henry:
He will claim he can speak it but find every excuse to not speak it. Even you don't get to know his backstory. He says one thing but actions suggest something else.
Though he can follow what you say. If you were to ask for a spoon in Italian he will give a spoon. So you are sure he understands, so have summed it up to maybe he has stayed in America too long that he has become unsure of his speaking ability, or doing a common thing foreigners do to drop their mother's tongue to adopt the new language.

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Mafia x Reader Scenarios
FanfictionThis book includes: Tommy, Paulie, Sam, Vito, Joe and Henry. The MC is written gender neutral. I just finished replaying Mafia 1 and 2 so I felt like writing this book.