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    pay for my girlfriend's master's degree,
-Is it cynical of me that reading that made me think, "oh gosh, that's probably a bad idea?"

If I had paid for my college girlfriends masters degree, I'd be pretty bitter about it at this point of my life. I mean, we had some great times together but that's no small investment and I bet I would have thought it meant we'd be together forever and well.... we weren't.

Good luck though and it's sure nice of you to think of someone other than yourself.