You dress terrible then ask how you look

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Tommy:

He opened his mouth then closed before pointing and nervously saying he thinks you can maybe change that to the different one in your closet. You did and it fixed it a bit so he nod, saying he thinks that looks better.

Paulie:

He just stared then smiled, saying great. Mentally he added "if you want to join the circus" but if this makes you happy then so is he. Just know he will snicker about it to the guys. When Tommy asked if this isn't a bad mean Paulie snickered this is still being nice for how bad you were dressed.

Sam:

He almost choked on his coffee then said great. Later, on his way back from work, he stopped at a store and bought a ton of clothes for you then returned. When you asked why he bought all this, he shrugged and said thought he should give you a gift.

Vito:

At first he wouldn't mind, saying great, finding it a cute thing about you. Though he debated if he should show you to her sister so she can fix your style up. But then when he became rich he wanted you to dress nice as well. So he did send you to his sister, who helped you get a better fashion sense.

Joe:

He snickered you look how Vito thinks of his apartment. You asked "so terrible?", he chuckled yeah, something like that. He assured you he likes terrible though so all fine. He chuckled you can both dress terrible together then. So you both dress terrible together, and both love it.

Henry:

He froze as he held a newspaper then slowly folded it. This felt more dangerous than any mission he's ever been on. One wrong move and he's done for. So slowly he said you always look great. You hummed then walked off so he slapped his newspaper back open and continued reading, feeling satisfied he dodged that bullet.

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