I never have cash either! And I feel you on trying to get money from people. If they're not going to have it right then, I'm done. I really hate the feeling of owing someone anyways, and then if they don't feel the same urgency to pay me back... A few years ago it took my sister 8 months to pay me back $200. That was the last time! I had to guilt her into it - she'd had plenty going in and out over that time, and I was pretty pissed at her not only for that but other things too.
Right now I've got two things going on with owing money. One is that DH's best friend bought a house, and DH and his dad have gone up there several weekends to help him do some work. That costs us extra gas money and fast food meals, because it's almost an hour away and friend is a stereotypical bachelor, so no food in house. That's fine, I don't care, helping a friend. But DH and his dad have decided several times to stop at Home Depot to buy supplies, because they didn't want the friend to get the wrong stuff. Ok... but now we have spent $250 on supplies... when will we get that back from friend, who is broke because they just bought a house that needs a ton of work?
If we end up writing it off and calling it a gift to friend (because I won't ruin the friendship over that, but that will be the end of spotting money for him...) I will just be annoyed because it's all been since the AMEX 10% offers came out, so if we were going to cover it anyways we could have used those...
Then my cousin and his wife have turned it into a competition about who is covering the bill. I think they think we have no money because we're still with the ILs... At this point I'm just like, you cover yours and let us cover ours! And the other day she told me, I have a Christmas gift for you I forgot, I'll give it to you next month! And I thought... noooo.... I didn't get her anything because I'm at a point where all of my friends are adults and buy what they want, and I'd rather we just hang out then buy each other stuff and add to clutter. But now I feel like I need to find her something before I go home next month, for her baby shower! I just want the craziness to end!