Consider tallying up all the costs. Have him pay half of the hotel but he will know that you are losing more than half because you have redeposit fees. Then try to take your mind off it by going somewhere else. Consider San Francisco, Los Angeles, Las Vegas, New York, or a city that has frequent flyer seats.

With Judge Judy, you both win. I think the "award" by Judge Judy is deducted from the base appearance fee. Say it's $5,000 per person. I don't know if it is that amount. If she awards you $1000, he gets $4000 and you get $6000. That is why people participate. If you do go, make sure you swear and have a mock fist fight! Then tell Judge Judy that she is neither pretty nor smart :D Tell her "they don't pay her because she's pretty. they also don't pay her because she's smart. they pay her because she acts like an idiot!"

I'm sorry, but anyone who is willing to go sit there on Public TV and let "Judge Judy" make some kind of joke out of the whole issue and totally ignore any sense of legality is anything but a winner, no matter how profitable their appearance is.

As a totally off topic, I saw her yacht down in Ft Lauderdale. Triumphant Lady, I think it is called. Kinda put the whole "judge" thing into perspective.

Hate to say it but one way or another the friendship is probably going to be strained if he doesn't step up and offer to pay you. If he doesn't pay, then you're going to be upset at him and if you ask him to pay, he may be upset at you.

Unless you've travelled with someone before, its usually better to let them book their own travel arrangements once you have decided on the flights and hotels.

I would never use my miles to book for anyone other than family and close friends because most think that because I'm using miles, its not costing me a thing. I was burned before when a 'friend' was going through some tough times and wanted to go to vegas. Flights were in the 800s that weekend so I used my miles to book him a F ticket. Initially he was appreciative but now everytime he wants to go anywhere, he asks for miles as if they were free. Even for a $99 flight he thinks its smarter to use miles and save the $99 for dinner.

That's because they're your miles and not his. To him, the miles are free.

For the OP, I'd suggest asking for 100%, since you wouldn't have made the arrangements but for his repeated requests, but at minimum, insist on anything out of pocket (hotel costs, taxes, cancellation fees, mile redeposit fees). Be prepared for nothing for exactly the same reason as above. He undoubtedly looked at your miles as wholly free, because to him, they are. We all know that's not the case, but others who aren't into this hobby tend to think that since you didn't have to spend money on the flight (of course, not entirely true, because there are generally taxes involved), you didn't lose anything.

Your anger at your boss is misdirected. First of all, he's your boss, not your parent. It's not his job to nudge employees to make sure their personal life (including vacation requests) are in order. Second, you're suggesting that your boss should cancel his time off because someone else forgot to request theirs? Most workplaces don't normally work that way. But assuming that is what you're suggestion, I assume you'd offer to reimburse him for any vacation expenses he's unable to recoup. After all, you want to hold everyone to the same standard.

LOL, was going to say the same thing! Judge Judy will give you back HALF, and dock you half because you shouldn't have booked nonrefundable...

My guess is that if you go to court, you will get nothing. You booked the room. He was not part of the contract between you and the hotel in any way. The room reservation is still valid, and there is no reason you cannot use it. Whether you want to or not is your own problem, not his.

I would just politely mention to him the amount of money you paid for the hotel room, and explain that it is non-refundable. If he values your friendship, he will pay half of it. If he doesn't, then you don't want to be friends with him anyway.

A lesson learned for OP.. I agree to take the lesson in its' good..

Good thing it looks like a small amount, and not an individual's life savings.:)

I doubt that any kind of trip cancellation insurance would cover this situation.

Did the friend know that you were booking a non-refundable rate? When traveling with someone else, I think it's wise to discuss this particular issue beforehand so that everyone is clear when the decision point is.

We were able to get everything but one room back, and he did say he would pay me back for that. Just figured I would post that in his defense.

Dumped and dumped again
 

I have an ex-friend who did this to me THREE TIMES and he now wonders why I refuse to discuss travelling with him. Worst one was an expensive Antarctic cruise where I finally paid for the second person and give the trip to another friend. It turned out to be a great trip.

It is always the same excuse as the OP's companion: he couldn't get time off from work.

Anyway, I've learned my lesson about this guy.

Sounds fair.. if indeed he pays you back..

You're just out on your FFP redemption cancellation fee then?

As long as he reimburses you for everything (including the miles reposting fee of $150), you're fine. Otherwise, your "friend" used you.

Are you kidding? Your anger at your boss is ridiculous. Your friend isn't responsible enough to request time off and yet you blame your boss for not giving it to him anyway? Then, adding insult to injury, you berate your boss for planning and taking his own vacation time? Totally preposterous.

Hmm, maybe I shouldn't post that. Original response deleted by user.

Anyways, I don't want to get too caught up on that part, but in a nutshell I fell that the situation is that my boss is purposely trying to turn what is a rather small incident into a very big brouhaha to make a political point without really considering the impacts on other people, related to this trip or not. It is not the trip itself but a whole string of issues leading up to it. The time off request was simply a technicality that he used, he was aware of the time off ahead of time.

But things worked out, I am Platinum so they waived the fees for me, he is repaying me for the hotel.