Here is the situation. I was with X for just under 3 years. Rewind two summers ago, he had his bank account hacked and I offered to support him for the month until the bank refunded the amount taken, at which point he would pay me back. Throughout the month, thinking he was going to pay me back, I paid for trips, concerts and the daily expenses with my savings and debt repayment funds (I’m a 20-something with student debt, while he is much older than me). One morning that month, I wake up knowing full well it is his payday and he can begin to pay me back, when lo and behold he has bought a new iphone. I never saw the money.

Fast forward to last summer we went on a trip to Mexico. We agreed we would each pay our own way, and I put it (stupidly) on my credit card. To this day, I have yet to see any of the money he owes me. It was the main factor in my decision to break up with him 2 months ago, which I strongly emphasized to him. Although he is in denial about why we broke up, and created a very different reason in his own mind, he promised to pay me back. I am very happy to be out of this relationship, but I just don't understand how someone can lack the basic human decency to pay someone their owed debt, when he knows full well how significant that amount is to me. My family and friends all have different advice, and I just need an unbiased opinion. Should I just get over it, and consider it a $2000 lesson? Or should I continue to push for the money, and if so how? A

It’s so lame that D-bags like this are allowed to roam the world with the rest of us.  What a disappointment on so many different levels. 

A, I don’t know how many times you’ve reached out to your ex, but I think you shouldn’t give up until you’ve nagged that dickface at least 10 times. The first couple attempts should be by email and phone.  If you just get radio silence after that, then I’d track down his parents contact information and let them know the deal.  For real. If he wants to act like a f-cking child about this, then he needs to be straight up told-on. Sure, this doesn’t guarantee your money back, but at least embarrass him.  A small payback, right? 

If after all this buddy doesn’t pony up, he was never going to anyway, so yes, the only thing you can do is consider this a “lesson”.  But I don’t think you should take that to mean you should never lend money out again. I just think it means that you need to listen to your gut a bit more.  I don’t want to rub salt in your wound, but when buddy flashed out his new iphone, um, that’s probably when you should have closed up shop. But I get it, you loved him; you had no reason not to trust him.  Any reasonable, kind, generous person would have done the same thing.  And for that reason you have to chalk this up to a one-off. You got burned.  It’s sh-t.  But move on.

Look, he managed to suck a good chunk of change from you, so the last thing you should do is let him suck anything else from you – namely, your valuable time.  You know?  The good thing here is that you’re in your 20s and while the money you lent out is far from chump change, it doesn’t sound like you’re living in a cardboard box because of it.  I have a good feeling that you and your bank account are going to be just fine. 

I hope this helps and of course I have no other choice but to leave you with this song….