Mafia x Reader Scenarios

How the first date went

You can absolutely skip this one if you wish to keep your own version of how the first date went.

I normally don't do "how" scenarios since those I usually leave up to the reader, but I just had an idea or two for this one.

Requested by: SamTrapani

Tommy:

He took you on a date before he had all the money from his jobs he does for the don so it wasn't an expensive restaurant, which he did feel bad for. It was just a small cafe, where he assured you to get whatever you want while internally begging you don't buy many expensive things because he's not sure he would be able to pay for the bill then. Luckily he managed to pay so he was very relieved it worked out. While walking back to your house, he awkwardly said he's sorry he couldn't take you to some fancy place but he hopes you still liked it.

Paulie:

He doesn't have the money for anywhere fancy and even a cafe made him too nervous because he kept worrying he might not be able to pay for it, so he just suggested a walk through the park. He didn't want you to know it's because he's worried for the money so he kept nervously making reasons as to how a walk in the park as a date is good for various reasons, naming different reasons until you finally assured him you are fine with a walk through the park. While walking around the park, at first it was a bit of awkward silence as neither sure what to say, which led to him awkwardly chuckling out stuff before interally cringing and wondering why he thought that would be a good thing to say. But luckily, eventually, the awkwardness went away as you both got to a conversation topic that both of you could talk about for a while.

Sam:

He took you to some restaurant. He didn't go too fancy but not cheap either, just made sure the atmosphere was nice in the place because he thought being able to comfortably talk was more important than how expensive the food is. But he didn't go cheap either since he didn't want you to think he doesn't want to spend money on you or that he's a cheapskate. He wasn't sure what to talk about since all he really does is his job and that's not something he can talk about so he was hoping the whole time you would start conversations. At the end, he offered to walk you home. While both walking, he felt a bit awkward but said he hopes you had a good time and that you will consider another date with him.

Vito:

He didn't have a clue where to take you since he knows many spots but has no idea if you would like them so he awkwardly asked you where you wanna go then awkwardly began naming the spots he has in mind, studying your face while doing so. When you frowned at something he named, he was quick to mumble that spot for sure not then, adding in an even quiter mumble good that he asked first. When you looked approval of the spot he said, he smiled and said good and now you both know where to go and how to dress. At the place, it was fun and relaxing, both having conversations and laughing. When you offered to pay, he was quick to say he will do it and paid before you could even pull out your wallet. Once out the place, he walked you home, awkwardly chuckling he hopes you liked today.

Joe:

He didn't want to take you to some boring fancy restaurant were it would be awkward, serious, and everyone's so fake. So he took you to a carnival he knew was happening somewhere. When you said that sounds like two adults trying to be teens again, he shrugged and laughed he would love to be a teen again. So both went and had a lot of fun. He always paid. When you wanted to pay him back, he denied it, saying it's only the right gentleman thing to do. Once the date was over, he called Vito to tell him about it, complaining to him about how fucking expensive carnivals can be, but overall how fun it was.

Henry:

He took you to a fancy restaurant, where he assured you to get whatever you would like and not look at the price. He wanted you to be sure he's a gentleman so he made sure he did stuff like hold the door for you, pull your chair back and push it back in once you are seated, etc. It was a bit stiff at first as he wasn't sure what to say, how to act, and just had a bit of trouble loosening up. But once you both began talking and got more comfortable in the restaurant, he didn't feel stiff anymore and managed to loosen up. Once it came time to pay and you offered to pay your part of the price since it was so expensive, he was already paying before chuckling and telling you he told you not to look at the prices.