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Loaning Money to a Love Interest

Someone I travel with occasionally and who is more or less a very good friend with benefits (for going on three years ...) is economically less well off than I am by a long shot. Still, we travel well together and have a lot of fun. I pay most everything and NEVER bitch about it. I am generous with meals, hotels, pocket money, etc. I have loaned him money in the past, but stopped a while back when I saw that I would never be paid back. The amounts of the loans were nothing I could not afford to never recoup. I cut off the 'loans' and gifts out of principle. I felt preyed upon just because I have more. I'm not wealthy, but I saved carefully throughout my working life. I got a series of very goopy e-mails from him over the past week, leading up to (guess what?) a plea for money for his mother, who is having hip issues. I turned him down flat, but nicely, and pointed out that family illness is a family matter. He has two deadbeat brothers who apparently never kick in. I feel guilty, but I also keep asking myself where this would all end -- paying the mounting medical costs of an elderly woman? Then burial expenses? What more? Thoughts on loaning money to FWBs or outright love interests?

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