She's probably leaving you that nuclear bomb she bought from the Russians. Oops, this thread is probably being monitored now.
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Whew!
So who has some uranium to sell me?
You never know what's going to stick with a kid. Your father could have made an offhand homophobic comment 20 years ago that everyone else forgot 19 years, 364 days, and 23 hours ago... but to your brother it was addressed to him from the person who is supposed to love him unconditionally. This is what makes homophobic language so insidious: not many people would intentionally use bigoted language around the target (which is why every racist joke starts with looking over both shoulders) because not many people are really bigoted, but it's a lot harder to tell if someone is gay than if someone is black. Combine this with how people let their guard down around family (both in what they externalize and what they internalize), and you can see how this scenario is plausible.
I assume from your volunteering your parents' religion that they have not expressed a lot of tolerance for alternative sexualities. Why are you surprised that your brother would take the opportunity to not only divorce himself from that tradition, but separate himself (however nominally) from those memories? Imagine what it would be like to grow up with your father (unbeknownst to him) telling you he hated you, that you were going to hell, that you were an abomination, also that he loved you, that you were the most important thing in his life... and tell me how your relationship wouldn't be complicated.
Or imagine what it would be like to rear children as that father, and tell me how you wouldn't feel guilt (again, we're talking about Catholics here). You can't go back and unsay all the things you said, but maybe you can go out of your way to help out your child now. Penance is not an outrageous concept in this scenario. I don't know how well off your parents are, but it's not like they're buying him a yacht, and I would also consider the implications (even if only subconscious) of specifically giving money for Christmas as opposed to an anniversary or birthday.
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Being transgender doesn't make your brother any more or less of a saint than he was before, or your parents any more or less of devils. Maybe he's taking advantage, maybe they deserve it. What would Jesus do? Not get bent out of shape, I think.
My father is far from a saint, but it takes a special combination of cruelty, greed, and heartlessness to do things the way my brother did them. There was no discussion ahead of time, which is what a grownup should do (my brother's 31 years old). If there really were those kinds of deep-seated issues, fine, sit down and talk them out. This was cowardly, mean, and underhanded, in my opinion. And the sheer gall to immediately follow it up with a sob story about how his girlfriend's kids won't have any presents under the tree, so would my parents please help out just... stuns me. It's like it somehow never occurred to him what impact this would have on my Dad.
And my parents (specifically my dad... my mom's retired) make a very comfortable living. Comfortable enough that my brother's Christmas present (about a week ago, before all this went down) was a gift of $19,000.00 and some change to pay off a loan. And that's far from the first time that they've lent my brother/sister significant financial assistance. They put 30k down on her house so she could afford it, have bought her at least two cars that I know of... I could go on and on. They've supported her even as she pursued a lifestyle that goes against their religious beliefs. My parents have worked hard to make sure that my sister/brother knew that they loved her/him no matter what, and that family was always family.
The whole thing just makes me sick. It's obviously a complicated issue, and I don't doubt that he had reasons for doing what he did. But it's inexcusable in my mind to not A) say something about it beforehand, B) consider the implications, and C) then immediately ask for more money. And to spring it all on the family at the holidays just exacerbates the whole issue.
Sounds like my sister and brother-in-law. Took 8 years of watching them take advantage of my parents while at the same time treating them like shit for me to finally say "You know what? I don't need pieces of shit like this in my life just because they are family."
I don't know why we feel we have to help out family members and keep them a part of our life when if they weren't a family member we would have ditched them long ago.
Someone build me a time machine dammit so I can warn my younger self!
And what really gets me is if you do decide to write out a family member from your life, even though they are a bunch of assholes, you're the bad guy. Someone explain this to me. Someone. Anyone.