Khortneeeeee3 got a letter!!

Dear Khortne3, 

Recently, a transgender friend of mine posted a 'go-fund-me' style blog on facebook asking for family and friends to send him money ($2000) in order for him to continue his transition into becoming a man. I support my friend in their operation, but I also know that they live in Los Angeles, drive an expensive car, and plan to attend college in the upcoming seasons. I liked their page, but did not contribute financially. A week later I received a message that started off chatty, but quickly got down to the point: can you send money to my cause? 

Though I understand the position they are in must be emotionally taxing, I too have medical bills to pay and expensive future plans that I'm saving for. Am I being selfish for not wanting to send $5 to my friend's Venmo account? Or is my friend's ask inappropriate when it seems like something he could pay for by himself in a short period of time with some planning?

My last questions is this: either way should I send him the money because he asked and he's a friend of mine, or do I tell him how it makes me uncomfortable to be asked for money in such a way?

-Financially confused

Dear Financially Confused,

This is a tricky, tricky problem.  If they were the letter writer, I would advise, NO NO NO, please don't hit up your young friends for money.  As we grow into adulthood, a necessary skill is discerning whom to ask for what.  There are friends you can call at two in the morning who will invite you over to do shots of whiskey and weep with you when you have a broken heart, but can't be relied on for income tax advice; there are those who will bring soup when you're sick, but aren't particularly astute about your emotional life, and those who can contribute money to your cause, but wouldn't hold your forehead when you're throwing up.  

These are merely a few of the categories; I'm sure we could go on and on, Financially Confused, but you get the point, which is that friends aren't interchangeable.  They each contribute unique and invaluable gifts to our well-being, and make life not just bearable, but awesome, and they teach us how to be good friends through their unexpected kindnesses.  The trick is to remember not to set everyone up for disappointment by expecting the wrong thing from the right person.  But alas, he didn't write, you did, so I'll focus on you.

It's probably a disappointing practice to decide what others can or cannot afford.  Me, I drink coffee out way too much; I should sing while I save, but I just get bored, exactly like Bob Dylan.  If your friend thinks he needs financial help with his surgery, there's probably no convincing him otherwise.  Someone could appropriately admonish me to save more for retirement by staying holed up alone in my bunker eating crackers and popcorn, but jeez.  It would bug the pants off me.  (Is that a saying, Financially Confused?).  So, let it go, about their car and their LA lifestyle.  (Did you see LALA Land, btw?  Me neither, of course, because of my movie disability.  But you knew that.  If you do see it, let me know if it's one I could follow.  Keep in mind that the last movie I understood all by myself had only three characters:  an African American man, a red-headed woman, and a white guy with dreds.)

The second thing I'd like to say is that gifts should always be given with generosity, and never because you feel coerced.  What your buddy doesn't understand is that you're the go to person for keeping his spirits high, backing his decision, and standing up for NO HATE.  But you're not the deep pockets friend!  (If you were, I'd so be hitting you up right now!)  So, say that.  Say, "wow, my dear one, it sounds so challenging on so many levels!  Emotionally, physically, financially.  I can't begin to understand all the stress that you're dealing with, and my thoughts are with you.  But alas, I'm not able to contribute money.  I wish you all the best!"

You don't have to explain why.  In the same manner that he doesn't have to explain why he drives a fancy car.  I would leave out the part about how it makes you uncomfortable.  If it becomes a habit, like the next go-fund-me is for his car, and then his new shirt, and then a fence for the dog (oh, wait, that's me...), well, bring it up.  But for now, leave it alone.

Let me know how it goes.  

All my best,

N'3lvra (Pronounced Court-knee, BECAUSE THE THREE IS SILENT!!!)