I’m worried about my manager and extortion. She has asked me to lend her money twice now and I haven’t gotten it back. She also is always asking me if I’m treating her to a drink or lunch, etc. context is that her husband’s business has gone bankrupt and they have 3 kids which I know is horrible but it’s also not my fault and I’m 15 years younger and struggling financially myself as I get started in my career. I wonder if she is using our work CC for herself too…

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You may be able to go to them or their manager (if you have a good relationship with them) and just express some worry that personal situations may be clouding their judgement. Or if you have some anonymous line you can be very vague in the scenario as to not give yourself away.

I'd also recommend setting a boundary with your boss that you are not in a position to pay for someone else's way. It's so unprofessional for a manager to even suggest this in jest.

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This is a major abuse of power. Do you work at a large company with an ethics hotline? If not, do you have any anonymous way to file a claim with HR? Even if you can’t be anonymous, report this behavior and let the company deal with it.

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In all the trainings I’ve done for work they say to let he or whomever know you’ve noticed some instances & behaviors or whatever. They can choose to audit the cards etc.
I’m sorry this is so tough

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I am so sorry. Just tell her no. If there are any emails regarding these exchanges, save them to your personal email. May have to go to HR.

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Even if there is not an ethics line in the company, there should be an ethics line in the state you live in (if in America) and file with the EEOC.

Document everything. Offsite storage. And talk with an employment lawyer.

Start looking elsewhere.

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Thank you all for your advice and concern. I so appreciate it 🙏 For some extra context - we’re a pretty lean startup team of 30 and my manager reports to the CEO. I’m also in the middle of negotiating my salary with my manager/HR so it all feels very tricky. I know that going to anyone at the org is going to get back to her. We’re also friends and so the exchanges have either been verbally in-person or on the phone where I’ve felt inclined to say yes out of pressure vs on an email where I would’ve easily declined. I don’t want to cost her her job because I know her personally and know how much she’s struggling but I also know this is such an abuse of power and inappropriate for her to be doing. We were just on a work trip and she kept asking “so are you treating me?” when we would get lunch. I think I really just need to set better boundaries but it’s so much easier said than done 😔

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because op is clearly unable to set boundaries from an authentic place and this is first and foremost a working relationship. "hey fucker you are my boss and this is a dynamic based on unbalanced power. furthermore you area friend taking advantage of that unbalanced power dynamic." seems like a far jump from "idk how to stop my boss and 'friend' from using me."

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You have to learn to set boundaries within your workplace relationships. She’s abusing your friendship. I’d document all of the times she’s asked you to treat her to drinks, lunch, borrowing money etc…She must make more than you. Do not make her families financial issues yours.

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No is a complete sentence. Do not start doing this ir there will be no end until you are ruined.

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