I am a 28-year old woman and have been engaged to a 30-year old guy for six months. We dated for a year before deciding to marry but, ever since the engagement, he has been asking me for money regularly. He says he is falling short all the time, even though he has a decent, well-paying job. I don’t feel like complaining because he keeps telling me that our resources are going to be shared soon anyway, and I understand that but still end up resenting him. I have never borrowed anything from him and like to be independent. Is this a red flag or am I just over-reacting?
You’re entitled to feel the way you feel because it is your money, and you have worked for it. While sharing resources is all very well, the most important thing you can ever have in any relationship is financial security and financial independence. If that is threatened, you are well within your rights to be upset. I suggest you tell him, as soon as possible, that this bothers you, because not saying anything may only lead to further resentment, which may affect your relationship in other ways. It also helps set a precedent before your marriage, because you should both walk into this lifelong commitment with your eyes open about what the other person expects.

My girlfriend keeps breaking up with me, and then asks for another chance when she has calmed down. I don’t know how many more chances I can give her, and she doesn’t change her habit. What do I do?
You have to both ask yourselves why these break-ups keep happening, because there is clearly an underlying issue that isn’t being addressed. She also needs to understand that these chances she asks for have emotional repercussions on you, which isn’t fair. Talk about what the big problem is and whether you genuinely want to be together.