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9

I once was in a similar situation, offering a gift to someone way lower income than I was, and I understand clearly the desire for anonymous philanthropy, but I would think there is room to be upfront about that. In my situation since we were both gamers and I offered gaming gear, I could pretend an implicit counterpart, that he use it when we were together. ...


9

If you intend to open the business, take his advice and retain him as your accountant for that business. Doing some free work for new ventures is a classic way to get new clients. The cost of a little time is the investment in landing the client. If you do not intend to open the business, send him a basket of chocolate or other goodies, something he could ...


5

I had this situation with a romantic partner. I told my ex-girlfriend (when we were together) that I would go with her and her friends on an expensive vacation - I was expecting a bonus at work. For weeks she became more and more excited about how I was coming. Things at my workplace changed, and I didn't receive any bonus. I simply couldn't afford to go on ...


5

Never under any circumstances force someone to take money from you. There is a reason he refuses to accept it (might be a wrong one, like assuming you can't afford it right now even though you can). By forcibly gifting the money you are denying his point of view which will only hurt your friendship. To solve your own ego issue (that feeling you are in debt ...


2

I have only some limited experience with these kinds of situations (from both sides). What I experienced in those situations is: This "I don't expect anything in return", as true as it may be, won't be how the receiving side usually feels in case of gifted money. It may work, where there's a deep existing friendship. But without that level of ...


2

I recently had a similar situation where I had to ask a friend for a ride. My friend did not want any compensation, and instead suggested I donate whatever compensation I had in mind to a charity. Knowing this friend, I picked a charity that aligned with their values so it was something 'for them'. If you know this person well enough, maybe you could tell ...


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