You ever try to feel bad for someone, but they keep making the same mistakes?

No, I pity them. Why feel bad if they do it to themselves? I just feel pity that they can’t do better.

I knew a woman who wouldn’t leave an abusive relationship. I finally got her to open up as to why. She was terrified of living alone more than she was of the abuse. He might feel similarly. She only left when she had a place to go with someone so she wouldn’t be alone.

Yeah, the kind of people that are always asking for advice but never take it or are the perpetual victims of life and take no accountability

I'd stay away from their relationship.. It's their business..

Yup

He’s a grown man. Leave it alone

Being kind does not always work, try ridicule.🤷‍♂️
I'm kind of joking, but not completely. Ask him how long it will be before he is caring for and financially supporting a child that is not his. How will he feel about babysitting while she is out catching loads?

I think it's worth remembering that relationships and feelings aren't easy. Knowing the right thing to do and doing it are two very different things. Most people don't want pain in their lives and they do what they think will best avoid it. Sometimes the fear of letting go is too much and so people will put up with all kinds of shit just to avoid the pain of losing someone. They don't quite appreciate that they are already dying a death of 1000 cuts.

For most people they get there in the end, though. It might take a while but they learn.

He needs to kick her to the curb. Six months to a year if she wants him she would shape up. Desperation on his part is only giving her more freedom.

Sounds like they both have commitment problems. Girlfriend? She isn't tied to him. However depending on their age I would kick her to the curb.

I learned a long time ago that habitual problems are because that person refuses to listen to the advice and encouragement of others, that it's best they learn on their own.