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I'm reminded of the story 'Gift of the Magi' (ya, I'm old). I can't help but wonder if the bf is planning the trip alone because you're working so much.
Maybe you can buy him the solo Caribbean getaway as the "expensive anniversary gift". That would solve your problem (what to get him that's really expensive) and his problem (not enough money yet to go to the Carib). And as an added bonus, he could then spend his money on beer and weed while he's there! And then you can go back to working just one job. If you reeeeally love him, you'll do it.
So you just want to buy a present so that he can give you one? Would any man react this way if his wife wasn't planning on buying him something expensive? But eh, I don't know the exact occation.
Oh really? Take the money to buy a gift for me, thanks~
Aww~! You obviously deserve better!!
YDI
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Eh... 1. Why spend so much on an anniversary present that you have to work double shifts to buy? Choose something meaningful within your price range. 2. So what if he wants a getaway by himself? Just because you're a couple doesn't mean you have to do everything together. Let him have some alone time. 3. It might possibly be a cover-up for his gift. If he wants to surprise you, I think that's a good way. Don't automatically think he's being an ass.
so save up your money and get yourself something nice instead.