Depends on the Individual
[QUOTE=BMax986;4534376]How do you respond if a regular you have a good rapport with, contacts you asking if you can help them out with some cash, via online app / money transfer. Have been seeing her at least once a week for the past 5 months. Pretty happy with the acquaintanceship. She's never asked for something like this before. Maybe it's because it's cold out? Amount wasn't much. Low end of usual donation, probably enough to get a room, or something. Am I a sucker for even considering it? Fire away.[/QUOTE]It depends on the particular lady. They are not all cut out of the exact same mold. I have loaned small amounts 5 times over the last 25 years. 4 of the 5 paid me back one way or another--I didn't lose anything.
The 5th--well, I do know her need was legitimate and not because of something she had done. We had had very good times together for almost 3 years and I didn't begruge her the money.