I started dating a girl about 7 years ago. When we met she was getting up on her feet and trying to find her way in life. I let my imagination take over and started envisioning her potential and what kind of life we would have together. I had never had the feeling of disarmed punch-drunk love that I had for her, and that probably clouded my judgement.
Throughout our time together she would reach out and ask for money for things… repairing a car, paying a bill, etc. We were getting closer the longer we dated, and I would always help her assuming that I was making an investment in both of our lives by helping her through a period of instability. In all I probably gave her about $15K.
After about 4 years of this I finally popped the question. She accepted and we were married after a brief engagement.