Do not "stay in touch with him, just to make sure he is okay." He's not okay and he will not be okay. He'll be less and less okay, until he makes major changes in his thinking that he is nowhere near ready to make. If you want to be willing to accept phone calls from him, you can do that for awhile. He will call and he will be looking for a handout or refuge from The Street. Stick to your offer of a bus ticket home. I think that's decent of you. Plus, it gets him out of your backyard, so to speak.

I believe every human being deserves my empathy. It's okay to feel that someone's plight is very unfortunate and even tragic. It's okay to shed a tear over someone else's pain. Those are not reasons, however, to become inappropriately involved in someone else's plan to live life crazy. He plans to keep drinking and drugging and not doing what an adult needs to do. Part B of his plan is to find those who will rescue him from consequences, but not demand that he grow up. I've been in your exact situation. It taught me a lot. Hopefully, you won't learn as slowly as I did. I learned the social safety net provides a great deal of help (more than you have any idea) to those who sincerely want to do the very hard work of becoming a ful-fledged adult. Even a person with psychiatric issues has the responsibility to do that. There are group homes for those who are so mentally incapacitated that they cannot think beyond the level of a child. Being in those homes also imposes rules and restrictions. "Every form of refuge has its price." (Eagles' song.) He's looking for the deal of deals, where he lives by no rules, and you provide him all he needs.

You will hear from him again. That will stop only when he decides you can't be suckered anymore. That will make you a real byeetch in his book. So when he tells you what a cold, heartless piece of crap you are, take solace in knowing that he is possibly about to give up trying to use you. Or, maybe, he's not the angry type . . . just the poor little lost lamb kind. In any case, you driving around looking for him just fosters the impression in his mind that you are available to rescue him. Don't do that because it's unfair to him for you to foster that hope.

There is a lesson for you to learn here. It is not right to become involved with an immature adult and foster that adult having an inappropriate dependence on you. It leads to the mess you found yourself in and are still trying to get out of. It would be nice, if all a lonely woman had to do was to find some dysfunctional but likeable male, offer him a hand up and thereby have herself a nice source of love and the fulfillment of fond dreams. If that were likely to work out, there would be no need for a nice girl to be lonely. It doesn't often (if ever) work that way. You were lonely and thought you saw a short-cut out of loneliness. There are no short-cuts to accomplishing the big goals in life, like finding a soul-mate. I say this to you because you are a magnet to men like this guy. He's probably not the last of his type to spot you and mount a charm offensive to melt your little heart. You see how it goes. The guy has problems, but, if only a nice gal like you would just love and believe in him, he could turn it all around. Yeah, right.

The next guy might not be a homeless alchy/druggie. He might be a struggling musician, or a guy starting his own business, who is so creative and has such a promising future, if only you would support him just until his band, or his business, gets established. Don't fall for it. You're at risk. You're susceptible to a good line of baloney, and you like to buy into a pretty fantasy. ("I promise I won't drink. Cross my heart.") This guy on the street needs to work on himself, and that's his problem. But you got some work to do, too, or you'll replace him with another loser who'll suck the life out of you.