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I'm planning a trip with friends and I'd like to rent a house for the weekend. The bill for such rental, housing 8-10 people, is $800-1,000. I don't want to pay the whole cost myself, but I am happy to pay more than my share if it means some people would go who otherwise couldn't afford it. I also want to avoid having to do a huge amount of math to split costs like groceries.

I can afford to cover the whole rental cost, and I'm kind of wondering if I should just do that, with the expectation that it'll come back to me in other ways.

How can I approach my friends on the fact that I do not want to pay for everybody, yet I'm willing to pay more than my share if it allows some of them to come should they're not able to pay theirs?

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    Hey there! Welcome on IPS. I allowed myself to edit your question to make it on topic, as "I'm wondering if I should just do that" isn't on topic on our site. Feel free to edit if you think I got you wrong. I also encourage you to take our tour to get to know more about how our site works. Have a great time around! – avazula Jan 19 at 19:31
  • Welcome to IPS! Could you edit in something about the distribution of "means" within your group? The answers might be different if there are one or two people who probably can't afford it and everybody else can versus if half the people are like you and could pay the whole rental if needed while the other half really can't afford much versus if it's just you who can afford more. Also, are there couples/families involved or is it 8-10 individuals? – Monica Cellio Jan 20 at 23:48
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    @Dave My cousin rented a huge house for about 12 of us and we all paid $100 each. She simply asked us to pay; it is a reasonable request. The cost included the rental home and groceries. Do you not feel comfortable just asking the attendees to pay? Then, if anyone says they are not able to attend for financial reasons, then at that point, you can ask, "Hmmm, how much CAN you pay?" And go from there, meeting the difference if you want to. Perhaps they can pay in other ways, by cooking/cleaning or loaning their car for transportation so the wear and tear is on their car. – Laura Jan 29 at 22:23
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When it comes to money and friends/family, I have had great success with one attitude. If someone needs financial help, and asks to borrow money or I offer it - I go into it expecting nothing in return. This eliminates resentment of not getting paid back.

For this particular case, try to keep it simple. I think you could safely start a conversation with "Hey! What is everyone's budget for this vacation?" From that you could ascertain what a reasonable cost could be for each person, perhaps the lowest number is the one everyone gets as their "bill". Say, for example, someone could only pay $50. An idea could be to just make the bill for all guests $50 , and then you cover the difference since you mention you could afford it. If it were me, and I could ensure staying in a nice place in a great location, I'd be happy to drop the cost per person to have more friends come. But, I don't believe it is in your best interest to have everyone's bill be different, either. That is over-complicated and if other people find out it will cause unnecessary drama, in my experience.

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I have experience of costs of an entertainment (office parties) being spread unequally so that very junior staff can come without incurring a cost that for them would be prohibitive. It is considered important that everyone who wants to come should do so, and it is so considered by the senior people who will be paying far over the actual costs of their own entertainment.

Now, generally accepted approaches in an office are not at all the same thing as setting up such an unequal sharing system for the first time and in what appears to be purely the context of friends holidaying together. Some people might be glad of the subsidy, but there are certainly people who would be mortified to feel any financial obligation to another person. Such a gift would be utterly unacceptable to them and very hurtful to their personal pride.

If your goal is to avoid deterring the poorer friends from joining the holiday, your idea of a subsidy might have just that effect.

If you are sure that the cost will be prohibitive for some of your friends, then why are you proposing such an extravagant holiday? If you are not sure, better to tell everyone what it would cost, and make it easy for those who don't want to spend so much to say so and back out gracefully. Also make it easy for you to back out of the idea if it is all too much for some of your friends.

If you want to make a gift to your friends, it would be far better to make it unconditionally. If you are setting yourself up to judge which of your friends is financially needy then you will cause all sorts of trouble.

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One approach I've had good luck with in the past in similar situations is paying the entire cost and saying something along the lines of:

Hey everyone, I'm going to buy this. It cost $800. If you want to chip in towards that, I'd appreciate it, but no pressure!

Generally, people who are able tend to chip in, and you do this without alienating anyone or forcing their hands. Since you're able but not eager to pay the whole cost, this doesn't have the potential of putting you into a disastrous financial situation.

In my experience, this approach has the added benefit of generating good will towards you along the way.

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That's a large amount of money at stake here.

On approaching bill splitting for the venue

You say you would not mind paying the whole amount if you knew it'll would come back to you should you be in need of something (whether it is an act of service or money, I guess from your question). The thing is, unfortunately, you can't know for sure whether it will, in the end.

I suggest you send them a mail. This mail should include:

  • The information that you found a venue for your next vacation all together. It implicitly shows your implication in the vacation organization on your own.
  • The price all in all and per person. If you only give the full amount, it may be difficult for them to immediately know how much they would spend in housing for that vacation.
  • A link to the property you found, so that they will be able to check it on their own and see whether they think it would be a great place to spend their vacation with you all. Be careful though, the more friends you are, the more people will likely give objections to the property you found. To avoid this, I suggest you add something along the lines of:

    Should you have any issue with this venue, please let me know, and together we'll find something that's best for all of us.

This explicitely says that you don't mind to look for something else, yet it asks for their help to find another property. That way, you won't have to deal with all the organization of your own. This is something that may be difficult to avoid when you plan an event with other people: if they see you're already organizing the event, they'll likely think that someone's already taking care of the organization and they don't have to get involved in the organization. If you choose write something like suggested above in your mail, it should avoid people to think that you'd like to deal with all the organization on your own.


On assuring them you can adjust the amount paid according to everyone's abilities

You say you'd not mind paying more than your share should it help people who may not be able to pay all of theirs. I think that the third point of the email already indicates that you're willing to find something that suits all of you, whether it is about the accomodation in itself or its price. Yet if you want to insist on it and clearly say you're willing to pay more if needed, you may want to add something along the lines of

If the price is an issue for you, please send me an email as soon as possible and we'll try to find a solution.

There's no need to be verbose in your message about what you're willing to do in order to help them, as it may embarrass them and they may think they'd appear as poor, or stingy, in front of all your friends. If someone indeed sends you an email telling you they have issues spending that much money in a venue, I suggest you tell them that you can find another venue together, or else you're willing to pay for the part of the share they can't afford. This way, it indicates that the most important thing is that you get to spend your vacation all together, but if price really is an issue to them, you can help them come. It'd prevent abuse (and you wouldn't end up in paying more for helping all your friends) and reassure them on the fact that they can come anyway.


On easily splitting groceries expenses

On the point of your question when you say that you'd like to avoid having to deal with the groceries cost splitting all alone, I could suggest you use an application like Tricount. You just have to enter the amount spent for each thing and the number of people upon which to divide the spending, and the app automatically calculates how much every one owes to the others. I use this app on a daily basis with my partner, with whom I don't have a joined account. This way, if either one of us spends something that'll benefit for both, we know how much money we owe to the other.
If you want to use such app for monitoring your expenses during your trip, I suggest you tell your intentions to your friends at the beginning of your vacation, and that you show them how it is used. That way, you release them of the difficulty of getting to know "yet another app", and they know it's important to you that you all deal with the trip expenses in a tracable way. I discovered that way on a road trip with 2 friends in 2016; it worked wonders.

If you're afraid they'll think you're stingy by doing so, just tell them you're doing this for simplicity. As a person who's extremely nice/generous and who don't mind spending for others, I know I struggled to remind my friends they owed me money. But if you tell them it is for simplicity, they'd be more likely to accept using an expense-tracking app. If you don't have a proof of how much you spent for the others, they're likely to forget at least a bit about it.

Enjoy your vacation!

  • @Llewellyn You're right, I did not cover that part. Thanks for reminding me, I'll edit my post ASAP to include info about this. – avazula Jan 21 at 8:05
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I've found it easier just to split it evenly at the start. This will start any necessary conversations about the wisdom of trying to have a such an expensive trip in the first place. Next, if the less fortunate friends indicate reluctance or decline strictly because of costs, you and your more affluent friends can say something like "don't worry about the cost this time, I've got you/I'll make up the difference." No different than covering a friend's tab when they're a little short or in a tight spot. Don't insist on them paying you back, no matter what they say.

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