Is It Reasonable to Ask My Boss for Reimbursement of Work Expenses?

A 27-year-old designer just tried to do the “no drama” thing after a team lunch, and now they’re stuck chasing their own money like it’s a side quest. Their company card failed, so they swallowed the bill themselves, expecting it to be handled fast.

Here’s the messy part, it was over $500, and their coworkers promised reimbursement would come quickly.

So now they’re weighing a meeting with their boss to demand the reimbursement, but they’re scared it could backfire on their job standing.

Original Post

I (27M) work at a small design agency where we recently had a team lunch to celebrate hitting a big milestone. When the bill arrived, our company card was declined due to a system error.

Not wanting to cause a scene, I covered the entire bill on my personal card, totaling over $500. My coworkers assured me I'd be reimbursed promptly.

However, weeks went by, and every time I brought up the reimbursement, my boss would brush it off or say they're waiting for approval. As a young professional, $500 is a significant amount for me, impacting my finances.

I've been patient, but it's becoming frustrating, especially with no end in sight for the reimbursement. I'm starting to feel taken advantage of, and this is affecting my motivation at work.

I've decided to schedule a meeting with my boss to discuss the situation and request immediate reimbursement. However, I'm torn.

On one hand, I feel entitled to my money back as it was a work-related expense. On the other hand, I'm worried about how my boss will react and if this could jeopardize my standing at the company.

So, Reddit, WIBTA for standing up for myself and asking my boss to reimburse my out-of-pocket work expenses?

Comment from u/random_potato45

NTA. Your boss should have handled this proactively. $500 is a lot, and you deserve to be reimbursed promptly.

The whole thing started when the company card got declined during that milestone lunch, and OP immediately covered the tab to keep things from turning into a scene.

Comment from u/coffee_guru78

That's a tough spot. If it's impacting your finances, you have every right to ask for what's owed. I'd approach it calmly and professionally.

Comment from u/starrynight_22

Definitely NTA. Work expenses should not burden employees. Your boss needs to understand the impact and prioritize your reimbursement.

After coworkers reassured them it would be reimbursed promptly, OP brought it up again and again, only to get brushed off with “approval pending.”

Comment from u/epicgamer2000

Bro, $500 is no joke. Your boss should respect your financial situation. Stand your ground and ask for what's rightfully yours.

This also feels like the coworker who used company benefits without contributing, and the argument that followed.

Comment from u/johnnydoe

I've been there. It's frustrating when work expenses linger unpaid. You're not the a*****e for wanting resolution on this.

Comment from u/pancake_lover

That's unacceptable. $500 is a substantial amount, and your boss shouldn't delay reimbursement. Asking for it back is only fair.

The delays are starting to mess with OP’s finances, because $500 is not “eventually” money when you’re paying bills in real time.

Comment from u/noobmaster99

NTA. Your boss should prioritize reimbursing you. $500 is significant, and you have a right to assertively request what's owed.

Comment from u/starlitdreamer

Your boss needs to understand the financial impact on you. Asking for reimbursement is completely justified. NTA.

Now OP is planning a direct meeting with their boss, trying to figure out whether asking for what they paid will earn respect or extra tension.</p>

Comment from u/sleepyhead_77

No way you'd be the a*****e here. $500 is no small amount, and your boss should have resolved this promptly. Advocate for yourself.

Comment from u/best_name_ever

You're not wrong to ask for your money back. Your boss should handle work expenses more responsibly. Stand up for what's yours.

What's your opinion on this situation? Join the conversation!.

Nobody wants to front $500 for a work lunch and then get stuck in “waiting for approval” purgatory.

Before you take on your boss, see what happened when an employee tried splitting an unexpected work expense with a coworker without asking first.