If there's one piece of relationship advice that everyone should follow, it's that you shouldn't financially support someone you're not married to. It's understandable to want to help pay your partner's bills if they're struggling, but it's a red flag if they're asking you for money, especially early on in the relationship. There's a very good chance that they're taking advantage of your kindness and desire to be a supportive partner. Normal, stable people don't ask their boyfriend of 2 months to pay their rent, because they know it's their responsibility to pay their own rent. An unstable person will jump from relationship to relationship, squeezing all of the resources out of their partner until they are fed up with being an ATM.
If you've been with someone for two years, you're more likely to want to treat your relationship like a marriage. Many people, two years into a relationship, will combine finances and have children together before getting married, which is a recipe for disaster if you break up. If you move into your girlfriend's house, help her pay the mortgage, and break up without your name ever going on the deed, you have little to no legal recourse to get the money you put into that house back!
A lot of times, the way you're treated when you're dating is the way you'll be treated in your marriage. If your girlfriend expects you to send half of your paycheck to her parents because that's what she does, then she's definitely going to expect that when you're a married couple. That is the situation that the guy in this story has found himself in. He has way too many financial goals on his plate right now, including paying for graduate school, saving for himself, and his girlfriend expects him to send money to her family every time they have an emergency. When you're broke like they are, everything is an emergency.