My 50-year-old always has women problems. He got a divorce after 11 years of marriage because she got hooked on drugs. It was her parents home for years and signed over to the both of them but in the meantime, she sold everything she could to pay for the rugs. He had nothing. I helped the best I could but told him I couldn't help more than I did. He gave up his rental (very nice place) to move with his girlfriend to a bigger place. After 5 years, it was over. No place to go. Met another girl, moved in with her. She opened credit cards in his name and maxed them out, then kicked him out. Investigation continuing in that. We had a big fight that time because he borrowed the truck to move his stuff out to store here. Left his stuff on the truck (and on a trailer he also borrowed) for 2 weeks. Made all of us furious. Anyway, met another one...moved in with her for a couple weeks. She was bipolar. Some days fine, other days radical. He moved out and begged to let him stay here. I had no bed so he slept on the floor. Said it would be for 2 weeks. He was no trouble since he worked 2nd shift and slept all day. Only had 1 meal here when he was off for the weekend. Found an apartment after that 2 weeks and told him no more moving in with other women and giving up his place. They move in with him or nothing. in fact, best if it was "nothing." he agreed but.....doubt that'll happen. He's not the type of guy to live alone or be alone.
i'm a 'sucker' for trying to help him all the time..that what my other son says but then I think about the years he lived on our property in a trailer rent free that his grandmother bought and lived there, my mother also lived there, and then he lived there with all my mom's kitchen stuff plus furniture, which he destroyed. The silverware was part of a set yet he threw it away. I love my kids. Gave me my gray hair.
But that's called being a parent and it's not being a bad parent at all. They need to grow up (at least mine do) and if it takes tough love, so be it. Don't feel guilty.