So I need advice. I have a gentleman friend who I care about very much. He's kind of the person that I describe as the "why couldn't this have worked" person. I think we'd be good together, but we've never really been on the same page at the same time. Lately, though, he's done some things that kind of bother me, and I'm not sure if I'm overreacting or if he's really being a bonehead.

So, some background. His life is kind of crazy right now. He's former military. He left the Army a few years before he would have been able to retire at a pretty high officer's rate. I realize that it's not my life, but it did kind of bug me that he did 16 years but didn't just stick it out another 4 in order to collect lifetime benefits. But like I said, it wasn't my life and we weren't together so I really didn't say anything. His plan was always that after getting out he would eventually get a civilian job, likely making more, and be fine.

Fast forward to now, he's essentially been out of work for 9+ months, has blown through all of the money he saved up from the military, and is living in either his sister's house, or his former brother-in-law's house. He can't afford his own place anymore. He's behind on all his bills. His only current income is unemployment and a cash under the table job making below minimum wage (probably over minimum wage take home, but still) working part time.

He's "looking" for a job. He wants to work in security or something overseas where he'll make a 150-200k for a year. That's fine. He was recently (in the last probably month, so not that recently) given two opportunities to pursue careers. One opportunity was for an overseas security position like what he wants, as long as he would pay the $180 for a background check (supposedly this is pretty reasonable, and for 200K a year I'd be down to pay 180 once), and the other is in the US working with an old Army friend. Great! Two options to pursue! Wrong. He (a) doesn't have the money to set aside for the army job because he's behind on his bills, and (b) is worried that his security check will come back poorly because he's behind on his bills. Okay... so what about the other job, you ask? Well, he doesn't want to pursue that until he can get some nicer clothing in order to be able to interview/start work. I get it, in order to work you need clothes. In order to get clothes, you need work. It's a vicious cycle, but at some point you have to figure out your stuff. His friend has offered to let him stay with him until he gets on his feet and can get his own place. The US job could turn into running an office in a large town that's really close to where my parents live and one that I'd be willing to live in too. It's a good situation. I just don't think he wants that job until after he does the high paying job for a year and saves money.

I feel like I'm constantly nagging him about looking for a job. But the thing is, I'm 27 and have a good college and graduate education, have a good job, am debt free now after throwing all my extra cash at student loans, and am very goal oriented. He's nearly 40, has a TON of potential, a good college education, but apparently no goals? I feel like I'm constantly nagging him, and when I brought it up his response was that it was really nice that I did because in the Army he was used to being given orders, and also it's nice that I don't just say "you'll find something" but actively talk to him about resumes, applying, interviewing, etc. And it's nice that I hold him to certain expectations when other people don't seem to care. That's great, but I don't WANT to be constantly nagging him. I shouldn't have to care more about it than he does.

Ugh, so this is really long and if you're still reading, I really appreciate it!

Anyways, last night he tells me how he's broken his laptop and will have to get a new one. Okay... I'm curious how it was broken. Well, apparently, the warranty on it was about to go out so he purposely put it in the oven to fry it. I'm floored. I guess he took it in to the Geek Squad and they said that it looked like negligence, so they couldn't promise if it will still be covered under the warranty. His response was "I hate to buy a warranty and not use it." Mine was "You have used it, you've used it for two years that you've had the laptop. It's like insurance. Are you going to burn down your house so you can 'use' your insurance? NO! Because that's fraud."

So I'm pissed. I'm SUCH a rule follower and I just feel rotten knowing that he so blatantly used the system. It reminded me about how my dad and my insurance company used to have insurance plans on the iPhones for like, $5 a month, but they had to stop carrying it because everytime a new iPhone would come out people would miraculously irreparably damage their phones and need to get a new one. I think it's wrong to cheat, but maybe I'm just a goody two shoes.

The other reason I'm pissed is how is he supposed to find a job now? I asked him what he uses his laptop for that a two year old laptop is too "old" (when I'm still using mine from 2008). His response was that he has a lot of music on there. So I reiterated asking him what he NEEDED it for. He caught on "to apply for jobs." And I asked him how he expects to buy all the clothes he needs or pay for background checks or pay bills so he passes background checks AND buy a new laptop because he purposely ruined the one he had that was still working.

Anyways, that's my story. I don't know if I have a right to be grumpy about all of it. He really is a good guy, I think he's just lost without the military and has dug himself a hole now. This is why I wanted him to finish out and actually retire in the first place. I'm so goal driven that it bothers me that he basically has none.

Am I justified in feeling pissed? or am I just being a jerk? What should I do? Advice please!!