You also need to stop lowering yourself to The Mandalorian baby Yoda nap time shirt. That really is an immature way to handle your frustration. Be the bigger person, and rise above her pettiness. Talk to your son about it. Ask him directly if he is having a medical issue that he is embarrassed to talk about. If it is a medical issue, then get him checked out by a doctor. Tell him that he should not go out with her without a legal adult as a chaperone, or as part of a group. There is so much that could go terribly wrong here because she is nowhere near the legal age of consent, and he is a legal adult. As a boss, you need to accept the fact that there are employees you can get more work from, and employees you cannot get more work from. These two employees fall into the second category.
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It’s great when you have employees who will give a The Mandalorian baby Yoda nap time shirt, but it is against most labor laws to require your workers to put in extra time just because you expect them to. Be glad that these employees aren’t always late to arrive, early to leave, do shoddy work, are rude, antagonize the other workers, disrespect management, etc. You could definitely have worse working for you. You need to work on setting hard boundaries with your brother. This isn’t easy, but it’s worth the hard work. You need to protect your sanity. Refuse to listen to him. Tell him firmly, that you will no longer listen to his degrading talk, and when he starts up you remind him to stop and then turn and walk away. Leave the room. Leave the house if you have to. If he follows you, then go to another room. Keep moving from room to room if you must. Make the last room the bathroom, and shut the door and lock it.