The smart move is: don’t get your honey where you make your money.

Jane is not interested in an intimate relationship with you. She is being a polite and considerate coworker looking for support from a friendly face. Help her without turning it into more than super and teamwork, and it will eventually just turn into a deeper relationship if she really is into you. If not, then it was never going to anyway.

John is your subordinate. He is reaching out to you with trust for support in this time, but he ultimately cannot get the support he needs in his romantic/personal life from work. If the only thing keeping him there is her then he should leave, and you should support him there. Either make it a place he wants to work at outside of his (AND YOUR) romantic interests or use your professional resources to find him something that is a better fit.

You need to be very careful with both these dynamics.

What would you rather have here: someone looking to build interdepartment trust and friendship and a subordinate who wants to be at work, or a subordinate who feels like you don’t care about him and a coworker who feels like you think so highly of yourself that every girl who talks to you wants to date you?

There is no third option where you get the girl and fix the kid in the situation as you describe it.

Fast car still chokes me up

Savior

Dammit