During one of my many trips this summer I did something I’ve never done before: I paid for someone else’s room with my credit card. And it did NOT go well.

Normally I book hotels through my company’s corporate travel site. This time, though, the hotel had a really great deal on their website that wasn’t available on the corporate site, so I booked there. Because I was traveling with a coworker, I went ahead and booked their room too. The fine print said that the offer was refundable until the day before we arrived, and that the credit card was just to hold the room. Nowhere did it say it was nonrefundable—in fact, it said the opposite.

When I checked in, I made sure my co-worker (who was arriving later) could check into her room without me. The clerk assured me it would be fine, but stupidly I did not ask if the room would go on her credit card. (I also checked to make sure that the lounge access that was supposed to come with my rate was showing up. It wasn’t, which should have given me the first clue that things may not go as smoothly as planned.)

The stay was actually quite pleasant, and the work part of our trip went quite well. The weirdness started after check out. As I was about to head to the airport, I got a text from the Home Warrior. “I was checking our credit card balance, and it looks like you were charged twice for the hotel. Can you fix it?” I only had a few minutes, so I ran back inside to find out what had happened. The manager on duty couldn’t tell me, and said he was only showing one charge. I pulled up my credit card account online, and showed him the two charges, but he was sure it was a mistake and would be fixed within a couple of days. Since I was out of time, I had to let it go.

As you probably figured, in a few days, it had not been fixed. I called the hotel again, they again couldn’t figure out what was going on, and said it must have been an error and would be corrected soon. They also gave me the contact information for their billing department, but said they were all “in a meeting” that day. I tried for three days to call the billing department, and could never get an answer. I was extremely frustrated, and swore I would never stay in this particular chain again. Ugh.

Finally, when I had basically lost hope and was trying to figure out how to dispute the charge with my credit card, I got an email from my co-worker (remember, the one whose room I paid for?). She asked me if my hotel bill had been weird, as they had only charged her $300 and she had been expecting $800. She looked at the statement in detail and realized there was no room charge, only charges for incidentals. Aha! Mystery solved. I hadn’t been charged twice for my room—I had been charged for both rooms! All I had to do was get them to refund my card and charge her room to her card, right? Hah. I should have known better! They kept telling me there was no possible way they could do that—the rate was non-refundable. Oh, and since I had gone through a third party (the hotel website!) there was nothing at all they could do. OMFG.

How did we finally resolve this? My co-worker submitted her expense report, got reimbursed, and wrote me a check. Drama! The moral of the story is that I will not try to hold a room for a coworker unless I am guaranteed by the hotel, in writing, that I will not be charged. Ugh.

Readers, have you ever paid for a coworker’s hotel room? Were you able to get reimbursed?