u/DubOSv10

Seriously, can someone help me understand...

1. What the hell is going on here? How did this guy go from having freaky sex with this girl (and others) to caring about her?
2. How can I help him out of this?

A friend has been seeing a drug addicted street prostitute for around a year in a half. Up until a month or two ago, he would pretty much just pick her up, have freaky sex with her, and drop her back off.

He didn't care about what she was going through on the streets, he didn't care who else she was seeing, etc.

Briefly: Friend is 42M, has been seeing working girls for many years and has never had an actual girlfriend.

Two Months Ago

He started getting closer to her and listening to her sob stories. She was telling him grandiose stories about how she got to where she was, how jealous other girls were of what was going on between them. He was telling her how intelligent and thoughtful she was compared to other girls. He started liking her outside of the sex.

He started picking her up while he ran errands (return Amazon packages, etc.). He would pay her $40/$50 afterwards with the understanding that she would come back after getting drugs, she rarely would.

One time he was founds her dope sick in the middle of the day and gave her $40. She was supposed to meet him later on that night but of course she didn't show.

Month and a Half Ago

More concerning, she started having him drop her off in front of trap houses. Like a month and a half ago, after one of his Amazon runs, he dropped her off at a spot. She was supposed to come out in "10 minutes" but took 2 hours.

Turns out, of course, that she was previously (and likely currently) fucking the drug dealer and they had some drama going on. My friend knocked on the door looking for her at one point and the drug dealer told him she wasn't there. Later on, the drug dealer asked her a bunch of questions about him. She claimed the drug dealer was "jealous" that my friend was always picking her up.

The drug dealer later got arrested and has been out of the picture (he has now been released but is out of the area). But it's still concerning that she was putting my friend in that kind of danger. Also, she initially lied about the relationship.

Most concerning, though.

Last 3 Weeks

1. Over the last 3 weeks, she has spent the day/night with my friend maybe 10-15 times. Sometimes he has her for 5/6 days at a time. He trusts her with his room keys and around his belongings. She also knows his real name and where he works.
2. He kept getting upset with her for taking a long time to get drugs. Sometimes she would pass out or fall asleep and he would spend an hour or two waiting for her or sending other people to go find her.
3. As a result, he now takes her all around town on his motorcycle and waits outside for her while she cops drugs. She has been a lot quicker about it, often setting everything up beforehand and texting different people using my friend's phone. Then they go back to the hotel or AirBnB and cuddle all day.
4. He spent his birthday week/weekend with her in an AirBnB all day.
5. He blew off two interviews with major tech companies to hang out with this girl.
6. Initially, he made her do drugs outside, she would stay outside for like an hour and he would get upset. She complained about having to go outside so he allowed her to do them in the bathroom.
7. She would take an hour in the bathroom, he would get upset, she complained about having to go in the bathroom and now she openly smokes drugs in bed and on the couch.
8. When she gets petty she will still find ways to leave for an hour, like having to "smoke a cigarette."
9. She kept getting money out of him. She told him $200 is enough for a whole week of drugs. That barely lasted two days, then she wanted another $100, then another $100.
10. After refusing to give her any more money for drugs that week, she demanded to leave the hotel so she can go work and get high. They had an argument, he took her back and he hasn't seen her since.
11. Friend has been kind of mopping and talking about her all the time. I guess she got into a fight before they met up last week and she feels "unsafe" in the streets. All the girls hate her, all the girls are jealous, and she thought about pouring acid on her face.
12. Friend says he's taking two weeks off before looking for her or any other girls again.
13. Friend is thinking about getting an extended stay with her for a few months, giving her a weekly drug stipend, and allowing her to work certain days with his approval.

She is clearly telling him everything he wants to hear to stroke his ego and keep him believing she really likes him but when she doesn't get her way, or when the drugs take precedent, she takes off back to the streets. Then he comes back a few days later and grabs her up again.

He keeps telling me she is making strides to do better and meet him half way or whatever. As if this is an actual relationship.

Seriously, help me understand what is going on and what should I do here.