Dear Calamity Jane...

Dear Bitter Amanda,

My grandmother once told me, "You can fall in love with a rich man just as easily as with a poor man." What are your thoughts on this? Or, how about this hypothetical: Say that you, Bitter Amanda, know two kind/smart/reasonably attractive men. Actually, first, let's pretend you are in a Disney movie. (This will make the rest of this scenario more reasonable. If you can call it that.) Now lets say you know two fine dudes. Mr. A, and Mr. B. Let's assume you have a good rapport with both-- you can goof off with each of them, share personal stuff without feeling too awkward, etc. In short, they both embody all the traits of a really really good friend, which is, obviously, important in a mate. By some Disney-fied twist of fate, they both propose to you. (Because the goal of most Disney movies is to marry off the leading lady. We will skip commentary on that for the time being.)

Consider the following: Mr. A gives you butterflies in your stomach every time you see him, but the money situation is spotty. Maybe he's a musician or an activist or something awesomely hip and idealistic. Spending time with him always feels like fireworks and flying, but you've been watching a lot of Discovery Channel and know that 90% of the time, that 'whee!' feeling wears off in 5 years, at which point you may still be renting the basement from your parents. Still, he's got all those other qualities mentioned above, and right now it's super exciting. Mr. B, you totally have a great time with, but he's not as super hot as the other guy. He's got a pretty sweet job, and can take care of himself, and you're definitely attracted, but you aren't tripping over chairs or dropping tea on your shirt like you are with Mr A. Mr B is just sweet, comfortable and caring, and also he occasionally pays for your cocktails.

Who do you pick? Do you think there's a stigma of picking one over the other? If the genders were reversed, would your answer be different?

--Conundrum Sam

Dear Calamity Jane,

Let's start thinking of ourselves as badass ladies, hm? (Forget the part where calamity means disaster.) 

Sure, we could pretend this is a Disney movie where you're the leading lady and I'm the talking tree/fairy godmother/teapot who gives you advice. But if this happened to be a Disney movie, and not your life, one of these guys would inevitably reveal himself as a villain out to get your father's fortune and kingdom. (We would also have some catchy songs and fun animal sidekicks, but that's not important right now.) This isn't a Disney movie. Sorry. I don't sing. Your grandmother wasn't wrong, but she also gave you advice from a different era. 

You raise some very practical questions, and a certain amount of that is expected and healthy. You want to go into a marriage with you eyes wide open on the financial stuff. That being said, I have a question for you: 
Why do you have to marry one of these guys? 
Why can't you just date one and decide if you can tolerate his bullshit on a daily basis? At some point you'll have to choose between them--and it sounds like you're at that point--but choosing one doesn't mean you have to marry him. Life isn't all about money--yes it's important and yes life is easier if you can pay your bills--but it's not everything. Go with the guy who annoys you less. Find a man who puts the toilet seat down and doesn't lie to you. (GOOD LUCK WITH THAT.) See how things go.

Is there a stigma attached? I don't know. In my experience, your life choices will usually be the source of gossip somewhere--no matter what decision you make. Gossipy bitches will always find something to hate. You can't worry about that. You do you. 

For the record, my answer wouldn't change if any of the genders in this scenario were different. Unless it was my gender, which brings up all kinds of what if questions about the course of my life leading me to write advice on the internet.
Solitarily yours,
Bitter Amanda