Dude, send me my straightener or you owe me $50.

As unfortunate as this is, he doesn't owe her $50.00. She mistakenly forgot to pack it, and asked him to do her the small favor of mailing it back to her.

And I certainly wouldn't spend another cent on him until he sent it to me.

^This. And this is the point I was making about re-evaluating the friendship. I didn't mean to imply that a true friendship was worth trashing over something small, but given the resentment on the part of the OP and the feelings she expressed about being generous with someone who was not willing to do her a small favor, I wouldn't spend another cent on him even if he DID send it to me. She clearly resents the inequity of their relationship and it might actually be a stronger friendship in the end if she didn't have so much to resent.

Some friendships have a certain ebb and flow to them. We all have had best friends at summer camp who we would have willingly given our lives for, then never see them again, or don't remain friends out of context. Some friends last a life time. Most fall someplace in between.

The OP has done just about everything she can do, except sent the mailer, and now it is in the hands of her friend. At this point, involving other people to make a bigger issue of it borders on obsession.

Keep On Dancing*

Seeing as how he is in Atlanta and I live 1000 miles away, I don't think I will be spending any money on him any time soon unless it's for something for his birthday in a few months. Regardless of whether he did anything for my birthday or not, I'm the kind of person that likes to make little gifts for my friends on their birthdays. But yeah, no more spending money on anyone but myself right now. Heck, I don't even have money to spend on anyone.

Really, like I said, the money shouldn't have been brought up in my OP anyways. It's not really the point of it all. I spent the money because it was on US having fun together. I didn't want to go to a bar and him not be able to drink because his money goes towards rent and his kid. I didn't want us to eat ramen all weeekend because his money goes towards rent and his kid. That was it, ya know? I spent money on me and him because I had money and he didn't and I wanted us to have fun weekends. So regardless of how our friendship does end up in the future, I'll never regret spending the money because of the huge amount of fun we had together.

I'm just keeping my fingers crossed come Saturday. But I've kind of let all of this go...even if he doesn't end up sending it, I might be a little butt-hurt for a bit, but I know he's not doing it because he doesn't think of our friendship as I do but because he truly is a lazy motha' eff. I'll still love him just the same as I always have.

And yeah, I definitely would never say that he owes me $50. I take full responsibility for leaving it over there. My fault, not his.

I know it's not about the money ultimately. It's just that you said you were emotionally hurt by this. So I'm trying to give you some pro-active things you can do that are specific that get you past the hurt and towards resolve. And yes, if he doesn't return the item, even if it is your fault that you left it, to me that is a form of stealing so in my view that means he does owe you the money if he refuses to return it. Especially if you make it soooooo easy for him. I mean really, is he a friend or not?

And yes, if he doesn't return the item, even if it is your fault that you left it, to me that is a form of stealing

You seem to be hitting the crack pipe especially hard today.

from dictionary.com

Steal - to take (the property of another or others) without permission or right, especially secretly or by force

You're wrong. And after all these years, I can't believe you STILL refuse to look up a word before going off. Mr Dictionary is your friend! Here's a link. www.dictionary.com Why don't you bookmark it?

Sheesh, Mr. Dictionary, it's just my way of saying that it is not ethical to keep something that isn't yours to keep.

You're absolutely wrong. He's not keeping it. He's just not sending it back to her which would require spending his own time and money. It would be NICE for him to send it back. But since he didn't take it (why can't you get that through your head?), he has no obligation to return it. He's not doing anything unethical; he's just being a jerk.

SHE is asking HIM for a favor.

Keep re-reading that last sentence until it sinks in.

Sigh, you guys aren't getting my humor. I don't mean manipulation or sneaky stuff! I mean joking around!

I guess I am totally missing what part was "funny" in your advice. Joking around isn't communicating what she is really feeling. Joking around is going to be masking what she really wants to say. HONESTY is the best play and once again you encouraged her to involve other people in this "joke". Adults handle things one on one. People have far more respect for people that handle issues one on one. Really doing it any other way disrespects the privacy of their relationship.

This guy is supposedly her BEST friend. It's not supposed to put him out to do a little thing for her. That's what friends are for. She's tried asking for it a couple of times. It's been suggested that she make it super easy with a pre-paid label where all he has to do is literally roll down a car window and drop it in a UPS box - not hard! YES, he is doing her a favor, but if enough time goes by and it becomes more and more clear that he has NO intention of ever returning it, then I think the game changes. How long do you give him? It's been how long already? So after say, a year, is it ok to say that it is wrong to shine her on? Yes, he's being a jerk but I also think that is wrong/unethical (or insert whatever word is semantically acceptable!) to keep forgetting/keeping/stealing/holding on to (or insert whatever word is semantically acceptable!).

Easy solution. We should each put a cardboard box in our hall closet and write "LOST and FOUND" on it. If visiting guests leave anything behind, we can deposit the item in the box so our intentions are clear. We are not stealing, we are finding.

The next time the OP gets there...1000 miles away, she can retrieve the lost item. Or... he can be a good friend and do her a small favor and mail it to her.

Moving on...

I have to confess to a perfect example of incorrect assumptions changing point of view as more information is revealed. When I first read the original post I assumed this guy was young and and had some time on his hands (helping her move such a long distance and having to fly back home, etc). Also, still in the bar stage of socializing and the ramen stage of nutritional awareness.

This sentence blew me away.

Really, like I said, the money shouldn't have been brought up in my OP anyways. It's not really the point of it all. I spent the money because it was on US having fun together. I didn't want to go to a bar and him not be able to drink because his money goes towards rent and his kid. I didn't want us to eat ramen all weeekend because his money goes towards rent and his kid. That was it, ya know?

Somehow, and I know it's not fair, this changes everything.

Forget about the straightener. Forget about all the "sugar mama" stuff and face the fact that your friendship may have been a diversion from his reality, and perhaps he isn't capable of being all grown up yet, and therefore not able to complete the task of wrapping this straightener in appropriate padding, going to the post office and selecting the proper sized box, addressing said box, and coming up with postage.

Then there is that little voice inside his head that keeps whispering, "Grow up...if you're going to waste you time playing with kids, it should be your own kid."

My new advice...forget the straightener. Remember how much fun you had as friends. Forget the money you spent...it's spent. Remember how this friend brought out a part of you that you like. Forget what you think a real friend should do for another unless it is to remember how you should treat your true friends, and remember to think more carefully about changing your expectations of people mid-stream.

Isn't there a part of you that knew from the start that he was a little bit unreliable?

Buy yourself a new straightener. Give up buying any bottled drinks to save the money. Use a water bottle.

Keep On Dancing*

This guy is supposedly her BEST friend. It's not supposed to put him out to do a little thing for her. That's what friends are for.

Maybe he's done a lot of other things that are big deals to her. He's lazy and young. Projecting our standards and expectations of friendship on this situation doesn't help.

How long do you give him? It's been how long already? So after say, a year, is it ok to say that it is wrong to shine her on?

That is for Brittany to decide. People make choices...do you overlook this and decide to be more responsible about gathering all your things in the future because you know he won't send them back? Can you forgive a friend for sleeping with your boyfriend? Can you forgive someone for gossiping about you? Can you be friends with someone that is a drama llama, or that does drugs, or even cancels on plans all the time. All of these situations are deal breakers for some, and not for others. You accept and move on while celebrating their good qualities, or you figure out they are incapable of meeting your needs.

wrong/unethical (or insert whatever word is semantically acceptable!) to keep forgetting/keeping/stealing/holding on to (or insert whatever word is semantically acceptable!).

Yes, but that doesn't mean she should start acting like a 13 year old and embarrassing him on facebook, or drawing anyone else into this situation. Their friendship and problems should not involve other friends or relatives in their circle. That's almost asking people to choose sides and that is just bad bad bad behavior.

This guy seems selfish and obviously isn't realizing how much his actions are affecting the relationship...and maybe he doesn't care. I don't know. If Brittany wants to be loving and patient she'll hang in there and hope the guy realizes a thing or two about friendship. If his selfish ways continue to unfold she'll dump him like a hot potato. No decision is right wrong bad or good. Do what is best for you based on the entire relationship, not just this situation.

Yes, he's being a jerk but I also think that is wrong/unethical (or insert whatever word is semantically acceptable!) to keep forgetting/keeping/stealing/holding on to (or insert whatever word is semantically acceptable!).

This is beyond childish. But if that's the way you want to play it, fine.

Your advice is a steaming pile of horse oats/shoes/feathers (or insert whichever word is semantically acceptable!). You are acting like a throbbing, erect tower/skyscraper/knob (or insert whatever word is semantically acceptable!). Please lay/cut/run (or insert whatever word is semantically acceptable!) off.

No, you are not silly because you have gone above and beyond for this jerk and he can't take the time to mail it back. He would be on my permanent black list.

No one can walk all over you, unless you like down for them.

I think your feelings are appropriate because he is not acting like the person you thought he was, which raises a lot of issues.
I sometimes have similar feelings with issues with people so my little mantra is "I cannot resent others for choices I have made". If I choose to do something, spend more money, travel more, always go that extra mile, I cannot always expect others to do the same. Just because I have 657687467 things on the go doesn't mean that I should be resentful when Miss X says that she can't do something because she has 5 things on the go.
Hopefully you don't lose a friendship over this issue but I think it definitely has created an opportunity for a meaningful conversation