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[quote=Anonymous]My best friend and I grew up together, often in the same household. She’s technically my friend, but we have a very familial relationship and she knows everything about my life. I say this context for my question. We are not technically related, but our lives are deeply are twined as a sibling would be.

I have grown up to end up making a bunch of money recently. I am going to clear $1million this year. I have never told her this, although I’m sure she’s aware that I have some money as I’ve been doing things like international travel and renovating my house. She might think it’s my husband’s money though. I don’t know. She is a nurse. They are not struggling by any means, but her husband is a stay at home dad and they live in a low cost of living area.

Our 40th birthdays are next year and I’m going to treat her to a trip to a high-end resort for four days. We’ve talked about this, but she’s not totally aware that I plan on picking up the cost. I was going to casually approach her and let her know that I have tons of hotel points so it’ll be fun to do this on points but that would be a lie. I’m just going to book us in an expensive all inclusive resort and have her show up and have an amazing four days.

Should I tell her the truth that I just want to do this for us? Or should I continue my small fib that we get to do this because of my work travel and related points?

It’s also strange to me that my life has changed so much in this manner and I haven’t told her or anyone. I know you should keep the stuff to yourself, but I generally feel like I’m lying through omission a lot with her about my financial situation, and this would be another lie through omission. 
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