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Buying Junk
So I have been seeing this guy since around the beginning of the year. He's a sweet guy and good looking but...there's some issues that I think will become big issues if we ever get around to getting serious with each other.

He has an affection for older granny cars. Stuff like the late 80's early 90's Buicks and Oldsmobiles. Which is just fine, in fact my dad had one and I get the nostalgia. However, he has accumulated 5 of these vehicles and only 2 of them are drivable. He just bought a '94 Park Avenue for $1500. Now, if this car was going to be a beater car he was going to drive around for a year, that would be fine. However, this car has issues. He told me over the phone he didn't check the fluids and trusted the place he bought it from that they were all good. Not judging him for the cars he likes but what makes this especially bad, his truck, the one vehicle he does depend on is in the shop which is apparently going to cost $900 to have fixed. Just the timing of things and the apparent lack of self-control. I know, I don't have any room to talk and many many examples of that. So I get it. I wouldn't be concerned if he was holding out for cars like these that were in better shape and something that he could realistically restore. He doesn't work on cars and can't fix mechanical problems so with him making $10 at a job he hates and all this...It is upsetting seeing him make these sort of mistakes.

I do feel that maybe I'm being too harsh on the issue. Not bitching him out or anything but I have pointed out that he could have put the money towards fixing his other vehicles. He also has a '86 Corvette which has issues running rich, an Old Eighty-Eight that needs a tire. He could have got 2 cars back on the road for much less than $1500 and had a vehicle to drive to come see me this weekend (I've come over to see him the last three times).

Again, don't get me wrong I have a good history of wasting money on shit and making boneheaded choices. The only thing I can say here is that he's not checking out the cars he's buying and they end up becoming yard ornaments.

The other thing is he just won't look for other jobs. He hates the one he's at, very underpaid and overworked and I've told him he should get on and look just to see what's out there. At the same time, I know what it is like to work at a crappy job and I know how scary the prospect is to go look for a new job, interviews and anxiety and so forth. I do understand this he does have a severe case of anxiety in general. All these are things I have at one point or another dealt with on some level.

I don't want to be too hard on him but I do feel that someone has got to push him to make better choices but if I do it there's a chance he'll resent me and I don't want to be seen that I'm controlling him. I don't know what to do here. I don't think pointing out how stupid it is to have 7 cars and none of them can drive 100 miles is going to work and I don't know how I can get serious with him between the distance.

We talk on the phone almost every night and usually for a good bit but often it is just me giving a monologue. He doesn't have much to say and I just run out of things to try to talk about. I mean, he's sweet and affectionate and a lot of good things but I'm kind of bored with him and this stuff is a bit frustrating for me.

Hopefully it's not just me being an asshole here.
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
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He sounds a lot like a guy I used to know. He would put so much money into cars which he would then promptly destroy that he ended up losing the roof over his head more than once. But he couldn't stop. He saw it as his passion and made the same silly mistakes over and over, to the point he would have unusable cars littering where he lived. There was just no telling him. They aren't the same people of course but your description of this guy reminded me of him.

I get the anxiety thing too. Heck, I have crippling anxiety in most avenues of life. So I get how he can be stuck in a job that he doesn't enjoy. Does he just flat out refuse to look for other work at all? Can he see you are trying to help him at least?

I don't think you are being an asshole for what it's worth. If you guys are long distance and he doesn't have a functioning car, something has to give. You are just being practical. I feel you will need to talk to him if you do want to make things more serious. Do you know if he wants to take things further? If you both do then you should address these issues with him (especially the transport issue, maybe the job issue can be later, baby steps), with the conversation starting with you are only saying these things because you want things to advance between you both.

And then the final thing to consider, do YOU want things to advance further? It sounds like the contact you have with him is leaving you unfulfilled. Do you think this is because you guys have had limited face to face contact? Things can get stale over the phone I guess if that is the main substance behind your guys dating.

Lots to consider, you aren't being an asshole though. I think you guys are stuck in a rut and need to move forward.
That's what I'm afraid of. He does like to go antiquing, in addition to cars he likes to buy old radios, clocks and whatnot. Which in itself is fine, but he does have probably 50 vintage clocks hanging on the wall. He also buys old console stereos from the 60's and 70's. So much that his stuff has accumulated in his parent's house. I have to walk sideways to get down the hall, mind you his parent's house isn't dirty or anything, just very cluttered with antiques and such. It worries me that this would continue in a serious relationship as I don't want to have 15 cars that don't run or him making choices like this that can clearly cause financial problems.

He does see that I am trying to be helpful on these issues, like the job issue. I think he knows he should look for another job but I believe he hides behind the anxiety and chooses not too. Won't even get on Indeed to just see what's around. The boss at his workplace is shorthanded and even said "you guys aren't going to quit are you?" and told him he should hit them up for a raise but he won't....he's too scared. I want to help him with this sort of stuff but I don't know that I can... Can I bring awareness to this stuff sure but some of this has to come from him.

170 miles is a long long drive. We try to see each other twice a month and take turns on a monthly basis, that's how it's been so far. It doesn't bother me so much to make the drive but I don't really like staying over there due to the clutter and with all the cats (they have 9 cats) and odors from all the old radios and whatnot it just kills my sinuses which I normally don't have problems with.

I do think the unfulfillment is due to not being able to see each other enough, this is a common issue with dating in the boonies. It does seem that he doesn't have much to say in general. I'll ask a question like what kind of food do you like and he'll reply with "ugh....I don't know" and be really general with everything. Similarly I have had issues getting out of him what he wants to do. Back on Valentine's Day I booked us a room in a touristy town thinking he might want to go to the shops and such since he likes antiquing...Since he never gave me any input I made all the choices on what to do then he doesn't want to do what I have planned. That stuff gets on my nerves. I can be indecisive myself, so it is a little bit of the pot calling the kettle black sort of.

Lastly, I already made plans with him in July to go to the beach and so forth. He's already paid his half. Part of me is thinking I should give him back his money and just go alone (again). I feel like I know that this is not going to work out between us in the long term. I would like to be wrong, I'd like to get serious with him but I don't see how it can be successful with what I am seeing. Definitely things I have to think on and try to work out with him.
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
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Being a sweet guy and good looking helps but a relationship needs more than that, it's a two-way deal, and this sounds like it's all one-way traffic from what you're saying. You are the one putting all the effort in, and I feel that even if things get more serious that will likely continue, and he will rely on you more and more. I may well be wrong but that's the vibe I'm getting from all that you've said. Communication is vital to any relationship, so you need to open a dialogue and have an honest discussion at some point with him.

As you say, it could be his anxiety getting in the way, and none of us are perfect, I'm not judging. If it were me I think I'd just continue with the status quo for now, to see how things develop but I'd certainly be looking for more input, sooner rather than later. Your gut instinct is already issuing alarm bells, so best to pay attention to how this relationship is making you feel.
Perhaps this beach holiday would be a good opportunity to really get to know him better, and get him to open up some more?

Is he planning to fix up these old cars that he's buying?
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@Bookworm I don't think it is so much he's not putting in effort. I think he's just used to not doing anything. As always there's more to the story. Some years back he had a wisdom tooth removed and they put him under general anesthesia. Something from it caused him to start having panic attacks all the time and apparently doctors suggested he go on disability. Not sure what happened, I suspect he had anxiety issues before all this and whatever happened made it worse. I think he's just got comfortable where he is. It seems he never got any sense of direction in life. Like he's 30 and doesn't have any idea what he wants to do for a career. Don't get me wrong a lot of people don't know, but I doubt he wants to work at an animal hospital cleaning up after parvo.

Yes communication is a big thing and when I get "I guess" or "I don't know" or just silence it does get old. I do think it is a mix of anxiety and maybe just that he doesn't have a response to things in our conversations... I'd rather it be anxiety over simply not having an answer.

When it comes to these old cars, yes, he thinks he's going to fix them up. The reality is, the math doesn't add up. It is insane to buy a car that is 25 years old and not even both to check the fluids, look for leaks and so on before you buy it. I've told him a while back that it doesn't make sense for him to buy all these cars. He spent $1200 on a 1990 Buick LeSabre that has no brakes...I just can't get over that he paid that much for a car he had to have a tow truck bring to his parent's house lol. Yes, sure, the engine is in good shape and interior is good and could be used as a parts car for the Oldsmobiles (TL;DR The Oldsmobile 88's, 98's and Buick LeSabre, Park Avenue and Electra of that vintage shared the same H body platform), but he isn't skilled enough to get a cherry picker to pluck the engine and transmission out of car.

He has a '86 Corvette that is in decent shape that he could have spent the money to get fixed and have something cool to drive around.

The other thing is that he uses these crap mechanics, the type that own a towing company and throw parts at cars. That's partly why it is going to cost $900 to get his truck fixed, assuming the guy guessed the right part this time. I told him that better mechanics cost more on labor but you wouldn't be paying for all these parts that didn't need replacing. But, perhaps I don't know what I'm talking about.

I'm doing my best not to come off as being mean or in a controlling way. I have told him, hey it's your money... But 6 or 7 cars and none of them can make the drive, that is stupid if you ask me.
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
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If he likes cars so much, has he thought about becoming a mechanic? He'd learn how to repair all those junkers without being ripped off. They make better pay than $10 an hour, and it'd be a job he has a passion for. He could work in the repair section of a mechanic shop with people he'd get to know over time, without being anxious around new customers, assuming it had someone else at the counter.
I have talked to him about getting into the automotive program they have at the technical college near him. I'm sure he could apprentice at a reputable shop and get more than $10/hr. I don't know that passion is correct though. People tend to be good at something but passion seems to come from a challenge or the outcome. Fixing a grandma's car for very little after she comes from another shop that told her it would cost a fortune might be where passion comes from perhaps. At any rate he has to start working getting over the wall of anxiety if he expects to get into a serious relationship with anyone, me or someone else. It's not really about how much money he makes, but seeing how he gets pushed around at work, making silly choices is frustrating.
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
Check out my stuff!

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