First, thank you for taking the time to read this. Here's what I'm dealing with:

I have been friends with this person going on 12 years. I met him when I was 16 (now 28) & he is (33). I moved at 20 & we lost touch for about 7 years & then he found me on FB & we've been keeping in touch ever since. Even though we didn't keep in touch, I remember us having a close friendship.

In the past 7 months since we've reconnected, he's asked me for quite a few favors, all which involved me loaning him money. First he needed $300 for legal problems and of course us being friends for so long I said I would help him. He did offer to pay me back, but at the time I felt if the shoes were on the other feet he would do the same for me so I told him he didn't have to. Then a few days later I received a text that he needed another $400 for the same legal problems. Shortly after, he asked if he could borrow $80. He was very grateful for all the help I was giving him and insisted on paying me back, but I told him to just be there for me when/if I really needed him.

Then I received a text a day before my birthday, I thought it would be him checking in to see what I would be doing on that day, but instead it was a picture of a pair of sneakers that he wanted me to buy for him on his birthday which is 2 weeks after mine. I responded jokingly "hey what about my birthday, what you getting me?" And he said, "tell me what you want I'll send it." But me being the type of person I am (humble) told him all I wanted was a happy birthday wish, no gift necessary. He said OK and then went on to tell me about the shoes and asked me if I could buy them for him. I never agreed and just changed the subject.

Then a week later I received a text asking if I could get him some designer sunglasses that cost about $100 more than the sneakers he originally wanted for his birthday. At this point, I'm starting to feel like he's taking advantage of my kindness. I call him out on it and his response was that I offered to help all the other times (which is a lie, he asked) and what I was saying was very insulting to him. Then he goes on to ask me to buy the sneakers because his birthday is a big thing to him & he would do it for me. I didn't respond. Then I wake up to a text the following morning that said " Wow, I guess you dont really give a smh".

Is he serious? I mean haven't I been generous enough? Again we have been friends for a very long time, and he says that he would do the same for me but I never ask so how would I know if that's true. Im not sure how to handle him. I don't want to ruin our friendship but I didn't think our friendship would be so costly. Am I overreacting? Should I get him the sneakers for his birthday?

I think you already know the answer to this...


He is clearly taking advantage of you... friends, family and money are always a toxic combination.

You should have insisted on ALL the money back from the very beginning, not wait for him to offer it. I'm guessing none of its ever been paid back...

Real friends don't impose on their friends financially like that... if he had any character.. he would have gotten a second or third job for the extra money...

Is it his fault for asking and taking? Or is all the fault yours for allowing this to escalate in the way it has? He was no friend and you should have seen that long ago. You have admitted as much from what you have written. Your first assumption that he is was in grave error. Correct your mistake NOW, and try not to be too mad at YOURSELF.

Make friends with a snake and expect to be bitten. You got your wake up call. Pay better attention.

You walked into this feet first. He saw you as a pushover from day one, and not once but 3 times. 'Humble' has no place in a financial arrangement of any kind, and telling him that you were sure he'd do the same for you is foolish - you didn't know him at all, because childhood doesn't count. I doubt that now you can even sue him for the $780. Kiss the money and all thought and contact with him goodbye. And given that you even have to ask people if you should have bought the sneakers, it's best that you refrain from lending anyone so much as a dime.

I agree. And it is disheartening to know that I must cut him off because of all this and that he was likely not a real friend to begin with or has changed over the years and the person he is now is not the person I thought he used to be.

You got it... people change over time... sometimes for the better... other times like this one... for the worse.

You are right. I am to blame for letting it escalate this far. I truly believed - at first - that he was sincere and would do the same for me. But that is not the case. I will consider your advice and learn from this mistake.

This is how con-men work... they paly on the good nature of people to take advantage of them. Sometimes they are people you know personally.

Its not always about cash...sometimes its bumming rides to the store, getting someone to babysit for free.....helping them move...etc.

YOu learn to spot the takers from teh true friends..... the takers never give back....or disappear the moment you need help.

We all have to learn the hard way.....for me? it was after wasting a weekend helping someone move.......when I desperately needed a hand for something a few months later on a weekend that woudl have taken 20 minutes of their time...the excuses started. (they lived nearby and were home the whole time)

The guy is a loser and you will be so much better off without him trying to get stuff from you.

I look at it this way...maybe you shouldn't have given him the money for the legal fees but you did...that was big of you I suppose. Beyond that, "offering to help" as he put it, is in no way the same as buying him expensive shoes or sunglasses. That right there should be proof and tell you that he is doing no more than using you and you don't need friends like that.

@odinn7 You're right, that is proof. Honestly, I don't know why I needed complete strangers to tell me this. In the back of my mind I suppose I already knew, but sometimes naivety makes you look for the best in people when there is none.

This is how con-men work... they paly on the good nature of people to take advantage of them. Sometimes they are people you know personally.

Its not always about cash...sometimes its bumming rides to the store, getting someone to babysit for free.....helping them move...etc.

YOu learn to spot the takers from teh true friends..... the takers never give back....or disappear the moment you need help.

We all have to learn the hard way.....for me? it was after wasting a weekend helping someone move.......when I desperately needed a hand for something a few months later on a weekend that woudl have taken 20 minutes of their time...the excuses started. (they lived nearby and were home the whole time)

Are you still friends with them? The people you helped move, or did you cut them off?

I had to work with them... but I no longer spent any time outside of work with them... and the next time they asked for something... (yes they had the nerve to do it not long after blowing me off) I flat out told them I had other things I had to do... rather than going out of my way like I did to help them before. No I no long did anything to help them.

You simply put your foot down... say sorry, I've got bills to pay and can't spare a dime (no need for details, keep it simple), and also don't negotiate with them about it... no is no.cut them off if they try to needle you for some smaller amount ( I bet he tries to do that)... I bet they stop coming around after hearing that a couple times.