I'm not entirely sure how any of them really would react so sorry if this is bad.

Requested by: Ta3ata3

Nucky:

He will feel unsure about what's going on, asking you what's wrong while walking over to rub your back and give you confused, worried eyes. As you told him, he will try to find a way to help you. If he knows there is a store that can always cheer you up, he will give you a ton of cash and tell you to go to that store and have some fun and forget your worries for a bit.

Eli:

He will feel a bit awkward, unsure what to do. He will try to assure you it's okay while rubbing your back, not sure if he should ask what is causing you to cry. As you told him, he listened with little nods. If someone caused this and he's still the sherrif, he will frown before trying to cheer you up by jokingly asking if you want him to go arrest them. Well, he says jokingly but he was half serious, already trying to remember where he left his handcuffs.

Margaret:

She will immediately drop whatever she is doing and rush over, worriedly asking you what's wrong. As you tell her, she will patiently listen and hand you some tissues to wipe your tears with.

Jimmy:

He will ask you what's wrong and if someone did this, looking ready to go fight whoever caused this. As you told him what's wrong, he listened while waiting for you to say something so he can help. Like a name so he knows who to beat up for this.

Gillian: (Because of this, I found out tissue boxes only got invented in early 1920s so... yeah, that's a fun fact for you.)

She will ask you what's wrong dear while pulling you down to sit with her. As you cried out what's wrong, she rubbed your back before getting up and walking off and returning with a box of tissues, handing it to you.

Richard:

He will sit aside you, nervously swallowing a few times, not wishing to come off weird or stutter at this serious moment before he finally asked you if you are okay. He mentally groaned at himself since you were clearly not okay. As you told him what's wrong, he stared with an upset eye, not liking to see you upset. Once you were done, he hesitated before wrapping his arm around your shoulders and pulling you a little shoulder, swallowing before assuring you it's okay and he will help you out with this the best he can.

Mickey:

He will be unsure what to do, nervously patting your back, assuring you it's okay, not even knowing what this is about but hoping saying that can cheer you up. As you tell him, he will watch you with upset eyes, not liking to see you cry. Once you were done talking, he will tell you he's sure if will get better so don't worry.

Arnold:

He will ask you what's wrong, gently taking your face so you look at him. As you tell him, he pulled out a tissue from his inner pocket and wiped your cheeks clean, assuring you it is okay, calling you gentle nicknames like dear and darling to help you feel at ease and calm down.

Chalky:

He will think someone did something wrong, asking you what's wrong, lifting your face to make sure you don't have any injuries. While you tell him, he will listen, nodding a few times so you know he's listening.

Nelson:

He will feel unsure what to do, frowning before asking you in that monotonous tone why you are crying. He isn't th ebest comfort as he does not know what to say and he tends to have that tone of voice that makes you feel as if you are just bothering him with your crying.

Al:

He will be quick to ask what's wrong and if someone did something, already ready to beat whoever made you cry. As you told him, he wrapped his arm around you, rubbing your shoulder to sooth you, not liking to see you crying. Once you were done talking, he nodded before forcing a chuckle, wiping your tears, trying to joke to cheer you up by telling you you will have no more water left in your body if you keep crying.

Charlie:

He will toss whatever he's doing aside and walk over, asking you why you are crying. Usually he holds your face in his hands, his thumb wiping your tears away while staring at you with these sad and worried eyes. If you like his Italian he will whisper comforting things to you and call you endearments in Italian.

Meyer:

He will wrap his arms around you, rubbing your back in a soothing manner that assured you it's okay. He will usually try to guess what's wrong so he doesn't have to ask it but if he can't think of what could have caused it, he will ask you what's wrong. He's a very smart man so he will immediately try to find a solution to solve whatever caused you this sadness.

Benny:

He does not feel empathy or sympathy like others, so for him this was just weird and he asked you in an annoyed tone why you are crying, not understanding it at all. Well he understood it a little but for him the answer was clear and he did not see what the point was of crying over it. When you told him he's not the right person to talk to, he stared before shrugging and saying fine, if you say so.

Gyp:

He will motion to you with a "what is this?" expression, asking you what's with you. As you cried out what's wrong, he listened. If this sadness if caused by someone, that someone better run because he's already storming out the door and motioning for all his guards to follow him.