Hip, old fashioned doesn't compute when you are "dating" online. You don't know this woman, can't even know if she's really female or available to you. Would you really want to be stuck for a weekend somewhere with a stranger who turns out to have bad breath or much worse, let alone pay for the weekend? That leaves "desperate" or "chump" as possibilities.

Casual friends do not lend large sums of money and expect to get it back.

If you are just friends you split costs. If you are wooing the woman, it's fine to wine and dine her...up to a point. If she never reciprocates by taking you out or cooking for you, she's a user. Users can sniff out desperate chumps.

I strongly suggest you do more decision making with your big head.

Interesting that you think generosity is a decision made with the small head.

I'm not talking about "generosity". That's a characteristic that is evenhanded between the sexes. If it's women whom you hope to bed who are the recipients of your largesse, that's something else entirely.

Do you think all your male friends are trying to 'bed' you, or just the generous ones?? The equality of generosity between the sexes is a whole other topic that I don't care to get into at this point.

I can't begin to imagine where you're coming from on these things.

You asked a question citing two specific instances and wondering whether you might be a chump. I answered your instances with my opinion. Lending a casual friend a lot of money and paying for a weekend away for someone you don't know sound like your asking for it. It also sounds like were these not women with whom you had "hopes" you wouldn't have done it. We're talking you, not me. I have never considered myself a chump.

Here's something my father told me, and I've learned the hard way that it's true: When you "lend" money to friends or family, you must consider it a gift. So don't lend anything beyond what you'd give as a gift.

Taking a shot in the dark, my guess is that you're not a chump or desperate, just someone who likes to help out others. However, there are boundaries that need to be drawn and there's nothing wrong in being up front with the person when you first start being "casual friends".

I think splitting expenses is the best route - it lets both people keep their independence and it keeps the relationship on an equal footing. And if one of the people can't afford to spend the money, there's no shame in admitting that.

In my opinion, if someone wants me to spend money on them and conveys that, I am inclined to question their motives. I think it's more important to be self-sufficient and get to know a person than to be expecting that person to pay for your entertainment or other financial obligations.

Bottom line, I'd like to know that someone was with me because of "me", not because of my money or their expection of obtaining something from me.