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My Boss Asked Me to Borrow Money, and Hasn’t Paid Me Back. I Confronted Her. Now She’s Treating Me Differently

I relocated from South Carolina last year and found a job as an inventory specialist in a warehouse here in Atlanta. It was a fresh start for me after my divorce, and I needed that badly. Upon starting my new job, I made friends rather quickly and have been enjoying spending time with them at work and outside of work as well.

The last couple of outings, my boss has popped up and been in attendance. She’s always buying rounds of shots for the crew and seems to have taken a particular liking to me. After exchanging phone numbers, we’ve spent some time talking casually on the weekends.

My Boss Asked Me to Borrow Money, and Missed the Repayment Deadline. I Confronted Her. Now She's Treating Me Different
Woman working on tablet. (Stock Image/Wallpaper Flare)

Recently she invited me to a comedy show, and I was surprised to see when I arrived that only she and I were attending. I felt a bit awkward initially, but realized that she wanted to forge a friendship with me individually, which made me feel good.

I have been thoroughly enjoying my new life, and I feel like I made a great decision in moving overall. However, my boss has done something that’s made me quite uncomfortable. She asked me to borrow money — not an exorbitant amount, but one that’s rather significant. I really felt bad for her because I figured if she had to come to me to borrow money, she must not have had anyone else she could ask. At any rate, a good bit of time has passed, and my boss has missed the deadline we set for repayment.

After considerable deliberation and receiving advice from other friends, I decided to confront my boss about the money. I did it in person, and the look on her face said it all; she was embarrassed but also angry that I had put her on the spot about not paying the money back.

Within that same week, she magically came up with the money and also told me that she didn’t think we should be friends anymore due to it being a conflict of interest, as she’s my boss and I’m her employee.

I’ve felt pretty sad about the “breakup,” but I feel that it might be for the best. I decided to plan a short trip to go back home to South Carolina to lick my wounds. I put in for the time off and also plan to work overtime to pay for the weekend trip. To my surprise, both requests were denied by my boss. Before things spiral out of control, should I confront my boss about the denials to ensure it’s not personal, or let things play out and see what happens next?

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