So my roommate heading down the road to financial ruin. Actually, he's probably there, but who knows how far he will go. I met him a little over a year ago. He's a super nice guy. Good friend. Prefers to be in a relationship with a girl over being single. We are in the same National Guard brigade. He was engaged and was in a debt management program to consolidate about $20k in credit card and personal loan debt. I moved in with him in August when I got a new job. We work together and shared rides, living expenses, etc. We were going to go to Atlantic City to celebrate my new job. I found out right as I moved in that he had broken up with his fiancee, whom he was fully supporting while she was still going to school. He even bought her a new car. While we were eating dinner, he told me that the Atlantic City trip would have to be put on hold since he didn't have any money to go. I said no problem, we can do it later on. He later tells me tha he is stretched to the limit financially and asks if he can borrow $500. Before I would consider it, I wanted to know what all was going on. He told me that he was behind on the payments on the car he bought for his ex (she was still driving it) as well as a few other bills (cell phone, etc). I delayed in giving him the money and he eventually stopped asking. So he meets this girl in November. She's super nice and a good match for him. I tried to tell him that he may not be in a financial position to be in the kind of relationship he wants to be in. He could casually date or whatever, but that would be it. He told me he understood, but not to worry. Everything would be fine. After about a month, he tells me that he is driving to Florida with her to meet her family (he moves fast in relationships). He tells me that they are staying at the house of a relative of hers and are getting free Disney World tickets. He had the vacation time at work too. I told him to take pictures and I would live vicariously through him. Half way through their week long trip, he calls me and says he needs to borrow $200 until payday (in 5 days). He asks if I could transfer the money to his account (we have the same bank). I agreed and asked for his information. He gave me the login for the website. I went on and got the necessary information. I also happened to notice that a Howard Johnson hotel in Florida had a hold on his bank account. He was staying in a hotel with her! I didn't ask because I didn't want to make it look like I was snooping, so I just transferred the money. When he comes back, he tells me that he has this great opportunity for me. HE BOUGHT A TIMESHARE! $170 a month for the next 10 years. He didn't need this. Not at all. He tells me how he can go to any of this resorts locations for a discount. He was going to try to sell these vacations on eBay or to friends and family. I tried telling him what a bad idea that all was, but he didn't listen. I think she had something to do with the decision. During lunch one day, we got to talking about the situation with this other car. I told him he needed to take some pictures and attempt to sell it. He owed way more than it was worth. I even offered to give him part of the payment to let me drive it back and forth to my parents house (200 miles away). He wouldn't do it unless I was paying all of the $396 payment. Come to find out he had made one payment on it since he bought it for his ex. The bank started calling him and he said he would be able to bring it up to date in March, which wasn't soon enough apparently. Over Christmas, I get a text message from him. It reads "The bastards took the car". I knew they would. I went through the same thing almost 10 years ago. In December, I accepted a transfer for work. I would be working an hour and a half away. I rented a room there and still kept the apartment. In January, he asked me if he could move his girlfriend in an rent would be split 3 ways. I said that was fine since I'm not there during the week. So thats the background. While at the apartment for a couple hours earlier, he received what sounded like 3 collections calls. Him and I both have state jobs that require security clearances. I know he wants to fully support this girl because thats the kind of guy he is, so I'm not sure how much of the living expenses he is paying and if she is paying anything at all. How can I relate to him the severity of his situation? CN: Roommate is in financial ruin, but doesn't understand how serious. How can I get the point across?