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Nat,
I feel you totally. You are in totally different relationship stages with these friends. That means that the expectation is different with them both. There is NOTHING wrong with this. Call the deadbeat and ask for your money!

I don't think it is petty, though you're clearly suffering more than she is for caring about what she owes you. Because of that, and because of her indifference to it, I would probably just note that it is an indicator that she doesn't share my values and either 1. Make sure I'm never in a situation where I have to cover her again or 2. Just stop hanging out with her (This is more likely what I'd do).

I don't think you're being petty about $30. I agree with you, it's the principal. This reminds me of a quote I read a few years ago: "If you loan a person $20 and never see them again, It was probably worth it."

Yipes, lending money to friends can be so dangerous (to the friendship)! We recently posted an advice column on this topic. There is definitely a line between helping a friend out and enabling their financial irresponsibility. Good luck!

Anna, Live Solid

These two situations appear to be worlds apart. Not only because of whom you gave the money to, but also what you gave the money for. I mean rent is one thing, but my momma taught me to stay home when I am broke. I don't think you are being petty. Big Worm said it ain't the money, "it's the principalities of the thang." Although I don't suggest doing what Big Worm did to get his point across, I can empathize.

@Tiny: I feel you. I was just trying to calm it down in my ripened age. LOL
@Colleen: I like 1 AND 2! Thank you!
@Jonez: High Five!
@Anna: In situation #2, it wasn't really loaning...Well, not intentionally. Someone didn't pay her fair share. I'm still not sure why.
@Steve: To the corner you go with the Big Worm quote! HAhAhAhAhAhAHAHAHA!!!!! Playing with my money, is like playing with my EMOTIONS!

The way I see it there are at least two things you can do.

1) Consider the fact that life is short, and getting hung-up about $30 is further shortening your life from the stress every time you think about it. You are giving her too much power - just let it go as a gift.

2) Or - Arrange to have dinner or lunch and when the check comes suggest she treat you so as to repay the money she owes you. Now you will find out what kind of a friend she is.

I never ever loan money, and I hate having money loaned to me, because I stress over things like this.

I think it is good that you see that you're never getting the $300 back - and maybe you should look at it that way for the #30. I would be upset too, and perhaps send her an email or something? Either to go out or just to pay it back.

You could just say - "hey, we haven't connected since that night out, so I know you haven't had the chance, but I was wondering if you could send me your money from the other night."

Something like that. I went in on a gift a few weeks ago, and totally forgot to give the buyer money at the shower. She emailed me and I put it in the mail. No worries. If she gives you crap, she's not a friend.

Yes, I agree with what some others have said above. Get your 30 back or at the very least make sure that you are not in that situation again. Perhaps the person forgot that she owed the money, if you bring it up maybe she will pay up.
PJD

I wonder if your "new celebrity status" is contributing to these behaviors. Before you created the blog and appeared in magazines, would these friends have asked you for money? Maybe now they see/know you're more frugal, so they assume you have it to give. You're a great friend/person for doing so. I would ask the friend about the $30, because like another commenter said, if she didn't have money, she should have not gone out to eat. I let my friends know up front if I can't afford to go out to eat this week. Money-it will help you determine who your friends are, among other things.

I had a friend borrow about $1K, and then yell at me when I asked her when I was going to get it back. We aren't close friends anymore.

I think you were right to lend the $300, and better still to not expect it back.

But the $30? Come on, your friend needs some lessons in being a lady!

@Nancy: You make points. I really would like to enact option 1, but I can't think of it as a gift. But I would like to move on from it.
@Natalie: I hear you...
@PJD: I won't be in that situation again. It's not worth it.
@Randi: Yeah, I've raised my profile but "celebrity status" is too generous. I am in the magazines because I'm a writer. Lindsay Lohan I am not. *snort* That being said, I have NO intention of becoming a "pay master." I will pay closer attention.
@GLM: High five!

I don't blame you. I'd want my money back too...

that being said, lending someone money is pretty risky and usually doesn't end well. It's pretty sad to have a friendship end due to $30 - even a "new" one.

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