Don’t get Severide wrong for a second - more than anything he loves his family. He loves being a father, a husband, and all that comes with it. But sometimes a man needs time away from all the estrogen in the house ( that includes the judgmental cat ) . He’s enlisted Casey, because it’s been awhile since the two of them hung out together. At first he thought that Molly’s would be the place to go, but he opted to take Casey some place different. Still with drinks, but away from the work environment. He’s sure he’ll catch an earful from Herrmann about loyalty and integrity later.
He sat, waiting for Casey to show up. Certainly they had some “gossiping” to do of their own. After all it’s not exactly a mystery that Cassandra’s best friend was staying in town for more than just moral support and as a free babysitter.