I need some advice on this confusing relationship?

[Anonymous]

My best friend and I have been hanging out together from time to time for years. Then dated. However, he doesn't manage money very well and only makes what he needs and spends all that he has. If he has extra he spends it all on scratch tickets. He always hopes for the big win. When debt piles up he tends to ignore them and pretend that they don't exist. He doesn't want to work hard for it because he feels he is too smart for society but no one would notice. people are nice enough to lend him things and he promises them to pay them back eventually he finds reasons he deems justifyable not to. For example, they make a lot of money anyway or they are a woman abuser and a drug dealer and he doesn't wanna help them. It comes to the point where he just wants to join the arm forces to learn discipline and structure. He wants a purpose in life than everyday boring tasks that he feels doesn't give him the adrenaline rush and proper structure because his childhood didn't give him the necessary tools in life or a proper father figure to be a decent human being. He wants to life life not live for money. He is in debt to me over $5k but he wants to enlist because he is unhappy. What do I do?

[Anonymous]

Let him enlist because he’s on the quick road to nowhere and maybe it’ll give him some structure. Honestly he probably won’t, because he seems to be the type that just doesn’t want to work, period, and makes excuses for it. It’s like a friend of mine who’s in 30s but lives off his girlfriend bc he was once a highly requested model and feels like he looks too good to work a regular job. He thinks the big break is still gonna come. But once you get to a certain age, you don’t have to give up on the dream but in the mean time you’ve gotta work like the rest of us, hopefully doing something he enjoys. That’s where your boyfriend is, thinking his brain is too big and he wants a certain sort of job or to get his big lotto break, and until then, everyone else can pay his way through life. That is an unacceptable way of living. He needs a reality check and some structure, so if he actually does go through with enlisting, let him. Maybe you need some time away from him too, to see what life is like apart and maybe you’ll find someone so childish and irresponsible doesn’t align with you.

[BarryLiverstone]

Is he your boyfriend or just your friend?

[Asker]

That's the confusing part. He was a boyfriend. But since he watches porn so much and fantasies about the exciting life. He wants to try out all these exotic things. He broke up with me but acts like we are still together. Still asks me for assistance on his bills he is behind but tells me it's better this way so he doesn't hurt me if he "accidentally" sleeps with someone else. He explains he is poly but he never actually tried sleeping around yet. But almost daily he talks about other women he sees or the fantasies he has with them in his head. Like the cashier we have take out Chinese at down our street. She does one nice thing of bringing the food to our car one day than explains to me of the threesome he fantasies with us and her. Yet any other day he calls me dear and sweetie and doesn't wanna sleep in bed alone. 😣😣😣

[BarryLiverstone]

So he is no longer a boyfriend. How will you get the $5k back?

[BarryLiverstone]

It sounds like you are stuck emotionally and financially. Got some challenges ahead. Do you have a plan or need advice?

[Asker]

He is going to military pt in a week or so. My focus is focusing on myself at that point and get ahead. I'm not sure where I'll go from there.