So, I hope this doesn't make me come off like a asshole, because truly i'm not, but I need some advice.
Ill try and be concise:
I'm teaching in Korea right now and i've met a truly wonderful girl here. My contract ends in the end of Jan, her's ends in March. After that, it's almost for certain that we'll go our separate ways. We both know this, it has been briefly discussed.
Difficulty:
I have a lot of student loans and credit card debt. I'm getting a huge chunk of cash (about 5,000 dollars) at the end of this month. I love her.
We're talking about taking a vacation together in September. It'll cost about 2000 dollars, which I could use to eliminate one credit card. I'd really love to do it, I could use a vacation and it would be an amazing time together. Ultimately however, in 5 months it will just be a memory and the credit card will still be there, minus the minimum payments.
Do I go? Do I pay off the credit card so when I go home my life will be easier? There aren't very many chances in life where a chunk of money can buy you extreme happiness for a week, right?
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Dropping a ton of cash on any vacation when you have a lot of debt is a bad call, as is calling off any sort of relationship because it could potentially end. You never know, you two might get together after, if either of you care to take the effort. If she is insisting on really expensive vacations over just spending time with you someplace nice, though, I wouldn't go at all.
Much as I'm sure the vacation would be fun, the smart choice is to postpone it while you pay off your debt.
It's not like your vacation destination is going away. It'll still be there when your debt is paid off. Besides, if it were me, I wouldn't enjoy the vacation because the whole time there I'd be second guessing myself for not paying the credit card off.
Though I'd really think that it isn't all of the story. Your contract is up in January, and I assume that you probably don't have anything for certain lined up after that end. The only way to justify such spending would be if you knew that you'd have the earnings for it to be a small dent and not a rather large loss. Unless there's something unsaid, you don't have that luxury. If that $2k is something you'll make back in a week, not a big deal. If it's going to take you even a month and change, it's really irresponsible. You said you were "getting" the cash, and if that means a one-time deal it isn't even something that should be spent at all unless in emergency. The usual "windfall" advice still stands: when you come into a chunk of cash (and $5k is enough to bat a few eyelids) you want to invest it. In your case, you're investing in yourself by reducing your debt so that you can, in the future, hopefully begin making money off your money.
You obviously want to spend time with this woman, so spend time with her. You don't need to spend thousands of dollars to do so. If you were to take $200-300 for something special, I think that's more justifiable.
In the end you should pay off the debt. Even if only because the next time you want to do something like this you don't want to be in the same position.
If the difference is that the trip actually costs 30% more because you're paying interest? Hmmm.
Consider it this way -- you are paying off your credit card, but you're immediately putting this trip back on the card. Maybe that helps to clarify it. Is going back into debt worth it? That's a better question, in my opinion.
I'm not entirely sure how the girl comes into the equation. Are you dating each other? Are you looking for a relationship? Are you seeing this trip as the only chance you'll have to have sex with her? You need to answer yourself as to your real motivations for the trip.
That being said, I don't think I've ever met someone who said "I wish I had traveled less," even those who were in debt.
Strictly speaking, you've been living in a foreign country for a long time. There is absolutely no reason you couldn't move to be with her, is there? It's not like you're not going to pick up your life at some point in the near future, why not settle it closer to where she lives? Unless of course the obvious is she's from the UK and you're from Canada or something.
But, pay off your debt first. It's amazing how much money you have when you're not paying interest or loans. It may take you a year to pay off that $2000 credit card debt, but not having it means you might have $2000 in 1/4 a year.
Good call :^: Sounds like you get the best of both worlds: a nice vacation together. And who knows, she could be the one! I know I'd pay waaay more than $2K to spend a week with the woman I'm going to spend the rest of my life with.
Also, this. The best way to stay out of debt is to continue to act like you're in debt. Until all of your debt is paid off, no less than 90% of the money you were paying on this card should go to the next debt issue. Rinse and repeat.