After seeing the yard, I wouldn't even go in the house... Seems like he's given up on life or he's just lazy...

I would no longer burn your valuable time attempting to help him fix what he is reluctant to fix.

I loathe dishonest people so his deceptive presentation of his age places him very low (as low as theists) in my book.

Well, I got out to mow the lawn and have done some spring cleaning too! So it is possible to change

A hoarder who is depressed, amotivated and trying to recruit someone to rescue him. Gee, that's unusual!!
Don't get sucked in, getting you to feel sorry for him is a strategy to which all too many women are vulnerable and although you may be resistant, don't help him sucker others. He can't be helped, only motivated to help himself and the greatest motivator is pain.
I also wonder where his family are and how he ended up in this state. It may be hard hearted to think, but perhaps he is reaping consequences he has earnt.

You don't have enough degrees to handle his issues. Even some of the hoarders on those shows, resist or undermine all efforts by others, to change.

He'll only change if HE wants to, and has lots of help - mentally and otherwise.

He needs way more than your help. It's not enough for him just to be able to clean up; chances are even if he did, he'd revert back to his familiar ways or other maladaptive coping behaviors if the issues that brought him to this point aren't addressed. Hoarding is a severe form of OCD, usually brought on by trauma or other mental health issues that have created a feeling of helplessness, and even though it doesn't look like it, it's a way of getting some control. It's hard enough to deal with a hoarder even if you're a professional with years of training in dealing with the disorder. Having struggled with OCD myself over the years, I'm very much aware of what it feels like for myself; that fear of losing control is very strong, but I have been able to accept and face the underlying issues, even though it's very difficult and an ongoing process to change and find healthy ways to cope... All you can do is gently suggest that he may have a problem that merits more than you can help him with, although at this point it sounds like he may not want to change. A lot of hoarders stay vehemently in denial until it gets to the point where they may have to be evicted. Or it turns into something like the Collyer brothers.

"Don is lazy and overweight, smokes pot and cigarettes and hates exercise." At his age this is who he is. I can't figure out why your real problem isn't men lining up & banging down your door, attempting to get your attention. That you would even consider helping this slob shows you're a caring person.

Your pictures reveal a proud elegant lady with a healthy lifestyle. I'd fly across the country just to meet you.

People will change only if they want to change, He does not want to change. You're wasting your energy and time on a lost cause, and yes, it's pathetic but unchangeable.

Perhaps a quid pro quo is in order. You help him organize if he agrees to spend time doing light hiking in the forest with you. The forest time will help him immensely with his depression and his physical self as well. As the depression lifts he will have more energy and will clean up his act.

Everything you describe is symptomatic of long term depression, the house and yard and everything you describe are symptoms.

Dating is no solution, it sounds like he needs professional help.

I suspect your kind efforts are enabling his lifestyle choices. He wants a woman? Wants a clean Home.
Let him get up and accomplish that.

Push this forward in your mind. Some woman accepts a date, is she going to see this guy, or the illusion you help him create?
Would you want to be that woman?

From my experience most hoarders have a mental problem. A neighbor's grandparents grew up during the depression. They did acquire property which later became valuable and they became rich. However, their habits never left. We would visit the house and it was unbelievable. So many future projects (barrels full of lead, a huge safe filled with who knows what and no key or dial number). It was so bad that the grandmother's water heater broke and she refused to get a plumber to come out as she was embarrassed to have some stranger see the house (the usual pathways cleared between stacks of boxes). Several of us tried, several times, to straighten things up but it was a total lost cause. Seattle has code laws to force people to clean up their act but it is hard to enforce. It often happens that a fire breaks out, insurance money is gotten and the problem solved. Unfortunately, it will always be a futile effort.
My suggestion, stay with things that make you feel good not frustrate you.

My question is why do you spend time with that person when there are animals at the shelters who really deserve your efforts. He's had a lifetime of opportunity and now he wants to lie about who he really is. Run. There are deserving people who could use your friendship.

Your patience is amazing. I don't judge people who live like this, however, I don't like to be around them. The level of slop you describe is a symptom of mental illness, and laziness to the point of sloth. Even his teeth are a mess. Yech.

Again, I'm amazed at the men you've got circling your life. I'm beginning to think you've got something out of kilter in your aura. Maybe you should seek quasi-professional help. Start with psychic cleansing and wear magic crystals or something.

Offer to clean it up for him, if you can keep anything you find. Buried in one person's midden heap is another person's treasure!

You are a better woman than I.
I'd be cutting Don loose, on every level.
There isn't enough money in the world.

You're beating a dead horse. Hope he's paying you well, because that's the only positive that will come out of this. But, if he should actually find a match, then that "loving couple" might make for a reality show all its own.

Even if you clean his place out, he will backslide and it will look the same in a few months. Do you want to undertake the job of continual upkeep? It sounds pretty clear he's made the decision to just wallow. If he decides to do anything at all, that's a first step. Asking someone else to do it for him is NOT a first step. IMO of course. Good luck, hon.

So many red flags for you or any other woman!

Nothing you can do about it. In the meantime please be careful about the corona virus it's increasing in your state