Should I do a nice thing?

Regular readers will know that I’m going to WDW in December with my ex, and two of my friends.

Mindful of the enormous cost of WDW trips, I have quietly subsidised various aspects of it. But there is another upgrade I’ve been agonising over.

On the flight out, Paul and I are booked in Premium Economy. This is significantly more comfortable, and offers much better food, priority check-in, priority boarding, and priority luggage handling. And a glass of fizz during boarding.

Anthony and Stuart are booked in regular Economy. I know from my outbound flight in February that those seats are not comfortable — it’s a nine hour flight — and I had the advantage of being in Economy Delight (same seats but extra legroom) and having a double-seat to myself. They’ll have none of that.

I can upgrade them to Premium for $550 total. (This is for the outbound flight. They are already in Premium on the return flight — the upgrade was so cheap it was a no-brainer.)

If I upgrade them, we can all sit together in two rows of two. We can check-in together. Super-selfishly I can put them in the row behind so that they can’t complain if I recline my seat! And they’ll have a much more comfortable and exciting experience. (Anthony has never been on a plane before.)

But it’s $550. I can find the money. But it’s not a trivial sum. (Later in the year I want to secretly book the WAT for all four of us. That’ll be somewhere near $1,000.)

So … do I book the upgrade? I’ve been agonising about this for weeks and I’ve been checking multiple times a day to see if the price has dropped. If it were less I would jump at it. But the cabin is slowly booking up and I may lose the chance if I don’t act soon. I really want to do it.

  • Do it.
  • Nah.

0 voters

Just because I think it seems really crappy to upgrade you and Paul and not them. I would find that really uncomfortable on a trip for all of you. It’s like booking yourself at GF and them at ASMo.


A year from now you won’t miss the money, but you will still have the memory.


Option 3: Give them the option if they want to upgrade and pay for it themselves. You’re paying a lot for things already.


I wouldn’t care about the flight upgrade but someone treating me to WAT!!! That’s amazing!!! You could let them know they have the option to upgrade the flight and let them decide (and pay for it); they might choose to use the $550 on something else at WDW (Disney math=bonus money)


Tell them you’ll split it with them, and then promise you’ll never mention it again.


They won’t think about it in that way.

I have vaguely mentioned it. Anthony (who can be difficult) said, “Well I’m not paying for it.” But then he’s an idiot and doesn’t know what he’s talking about.

This is what I keep thinking. I want them to have an awesome time. Because that will be awesome for me. And this is a once-in-a-lifetime trip. (Haha. But it is in the sense that I will never subsidise another trip for them. This is partly me being nice and partly showing them what life can be like if you have a job and you stick with it. They’re slowly appreciating this already. Indeed, all this is what inspired Anthony to get a job in the first place.)


It’s a really great way to start off the trip. Money is money. The driver to this decision is your thoughts and feelings. If you will have any resentment for providing it to them, then don’t do it. If it’s a sacrifice for you in any way, don’t do it. If you’re genuinely happy to do it and want to do it, even if they don’t acknowledge it, then do it.


I agree with this. Give them the option and let them decide. You’re already doing all the planning and paying extra for stuff…if they say no than it’s their loss.

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Okay, so…I actually had to think about this one for a bit, because the “obvious” answer is to say do it! I mean, it comes across as mean to not.

But not only are there other options (as exemplified by a few of the comments here), there is also a dynamic that can be created when you start paying for things for others.

Now, I’m merely speaking for myself, and situations where this kind of thing has happened…but when you pay for something for someone else, it automatically creates an unintended sense of obligation on the part of the other person. It is like if you give a gift to someone, that they suddenly feel the need to reciprocate (even if that wasn’t your intention).

I wonder, for example, if they might suddenly feel a need, even if only subconsciously, to do what you want during this trip even if they don’t want to. Even if they already WERE planning to do that, anyhow! But before, it was out of an appreciation for your mastery of Disney, and now it is because this guy paid a decent sum of money for us!

In the end, you are not taking anything away from them by NOT paying for it. And, if you REALLY want to pay for something, it might be better to wait and surprise them as you approach the end of the trip, so that any sense of obligation is minimized or mitigate by all the previous days.

I also would worry that it comes across as, figuratively speaking, prostituting yourself for friends. Meaning, that it could come across as trying to buy their friendship in a way you didn’t intend.

Obviously, none of these feelings may actual come to fruition, and may not be applicable based on your current relationship you have with them. But I do know in the past when we have done something for friends of ours just to “bless them”, it resulted in creating an awkward dynamic for a while that didn’t exist beforehand. So what came across as a nice gesture actually resulted in throwing a bit of a wet blanket on our friendship for a time.

So, I voted “Nah.” And not because I’m mean or selfish! :slight_smile:

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While sitting in first class last year and watching ppl board the plane a couple of teenagers stopped to quickly say ‘hello’ to their parents seated in front of us. Other passengers noticed and asked about the situation and began laughing and teasing the family about putting the kids in economy. It was all good fun, no one was mean about it at all; even the teenagers laughed and smiled. I’m just sharing the story b/c it’s funny and to demonstrate that it happens that groups split for various/unknown reasons on the plane.

This is a hard question and no easy answer. As you said, its not a trivial sum of money for you to cover both of your friends.

And there will be dynamics created because of it, or because “not of” it.

All I would say is that if you decide to do it. Think of it as as gift and move on. You can’t expect anything back from it… including gratitude (although gratitude SHOULD be there, you can’t expect it).

Since you are planning to pick up the tab for WAT, and that is still a secret, you could always do the upgrade, and decide on WAT later. You could also decide to let them choose the upgrade or the WAT. They might not mind coach if they know they are being given something else.

Personally, I would NOT be offended if I were in their situation and had to fly coach. It’s $250 each for them to upgrade on the way out… they can make that decision if they want to. Its such a small sum that, given the course of almost 8 months before the trip, they could certainly save or earn that much to increase their budget ($32/month between now and December).

Good luck with whatever you choose!

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I think you may some excellent points.

However, the friendship dynamic in this case means they don’t really apply.

I’ve paid for the two of them to go on holiday with me many times. And they’ve never felt any sense of obligation to me! (And my motivations haven’t been entirely pure. I took them on a road trip to Scotland one time because I’d only recently learned to drive and I was anxious about taking such a long trip on my own. Anthony was a great person to have in the front passenger seat and that really helped with my confidence — both on that trip and subsequently.)

The original plan for the December trip was that I would pay for everything. But I wanted them to have skin in the game, so I asked them to pay for their own food and merch and suggested a monthly savings plan. They got super-excited about the trip (because I kept swamping them in propaganda and they discovered YouTube) and realised that they wanted to spend more money than they could afford. So for the first time in over a decade, Anthony got a job. Six months later he was able to upgrade to an even better job, making pretty decent money.

At that point I realised it didn’t make sense for me to pay for everything. They have money now. So I backtracked and asked them to pay their full share. I felt awkward in doing so, but the circumstances had materially changed. Anthony accepted this without argument or awkwardness. Equally, he wanted to be prudent. So when I said Paul and I were flying Premium, he said he didn’t want to pay the extra. When I booked their flights the extra for the return flight was so small, I just paid it myself.

I’m genuinely torn about the outbound flight. On the one hand I think it will be nice to sit together and I want to watch Anthony looking out of the window. He’s already excited about it. I think there are practical reasons why it makes sense. (Can they check-in with me and Paul at the Premium desk? Or do they have to join the huge Economy line? Annoying for us all if they do.)

On the other hand, they’ll appreciate Premium so much more on the return flight if they’ve experienced the horror of regular Economy on the outbound. I’ve picked seats that are close to mine and Paul’s so that we can basically deplane together and race towards the immigration lines.


100%. My motivation is not some kind of quid pro quo. And they’re not like that. They won’t feel obligated.

My motivation is, in a way, selfish. I just think it will be easier, and kinda nice for me.

Well, if it is mostly for you, and they aren’t making you feel obligated, then it is up to you. If that’s how you want to spend $500, then do it!

Just don’t do it out of a sense of: guilt, obligation, or pressure to do so from them.

But if you want to… go for it!

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They might not think of it that way, but if I was the one in your position, that’s how I would feel.

Here’s fun, though … I have two tickets for entry into the business class lounge at Heathrow (which is awesome) and so once we’re all checked in at the airport, Paul and I will be ditching them to spend the waiting time there.

There is no way to avoid this. The tickets have to be used and there is no way to add Anthony and Stuart.

But I think they’ll enjoy exploring the airport and would probably be bored in the lounge.

I feel zero guilt or obligation, and they have placed zero pressure on me.

I just want to do a nice thing, really.

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There is your answer, then.

In light of the bigger picture you painted of the situation, I might change my answer to “do it”, but present it in that way! Just tell them, “As I was thinking about it, and just felt the whole thing would be simpler on me if you guys were sitting with us. I just prefer it that way.” It is less about you doing a favor for them, and you doing a favor for yourself.

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What are you, Anna Delvey? LOL. That is very generous of you.