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Background: Me and my school days friend [we did our school till graduation together, we are the best study buddies, project buddies] are very good friends and make it a point we meet each other at least once a year like go to some resort for couple of days, hiking, conference.. etc. our spouse/family know us well.

Problem: I insist on keep our money spent on the time together kept separate not owing each other as we are earning ourself and responsible adults. But this friend always some or the other way cross this line. For instance, This year we had planned conference + hiking. Friend had booked the hotel for both of us without informing me. In-spite of me telling not do that several times. I said, will pay you back but friend insisted on not necessary, you can take care of restaurant charges.. etc.

I do not like such things. This friend is not taking money booked for the hotel [which is quite expensive] and the money spent in the restaurant did not even covered quarter of what the hotel cost. How do I fix this, would it work:

  1. I buy gift and post it to this friend's home.
  2. Next time me-booking hotel, I do not want to wait till next year. So should I post money ?

Any help way to make this friend understand ?

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  • Unfortunately, this question appears to be asking “What should I do?”, which the community has determined to not be a good fit for Interpersonal Skills Stack Exchange. We can’t decide for you what to do; after you determine what you want to do, we can help you with your goal, but we can’t make these decisions for you. Sorry. If you're sure that you want to pay part of the hotel costs with me and your friend don't let you, then we can help. – CaldeiraG Jun 9 '18 at 17:21
  • Is this friend sexually attracted to you? – Stephan Branczyk Jun 9 '18 at 21:22
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What a nice question. Instead of people asking how to make "friends" pay back money that they owe, here is someone who actually wants to pay back! Many people would wish they had friends like that!

Now seriously, if your friend pays for things and doesn't want to be paid back, then you can assume that your friend actually enjoys doing some good deed. If you believe that your friend can afford to pay out, then everything is fine. There is no need to pay back. If you can do something good for your friend, then do it. Don't spend money on things that wouldn't be purchased otherwise. So don't buy a present that you would otherwise not have bought. Your friend wouldn't want that. Paying a restaurant bill is fine because that money would have been spent anyway (shared between you and your friend, instead of you paying alone).

If your friend can't afford it, that is a different matter.

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  • Can you back up this answer with personal experience or references? – CaldeiraG Jun 9 '18 at 20:34