Friend's daughters infatuation with older boyfriend

Lately I've found myself in a very odd position. A couple years ago a friend of mine introduced me to a family he was friends with. They would often come out to social functions and they were in a poor situation with a single mother having nine children with two different men. She home schools the children and lives on food stamps, dumpster diving, and occupational child support.

Doing little favors for the kids was something I didn't mind doing. I taught one daughter how to drive. I try to help one of the more socially maladjusted brothers develop better social skills. I helped the youngest (16) daughter with her artwork and academics. We had some heart to hearts about trying to convince her mom to let her attend a school or at least some extracurricular summer courses with people her own age. This did not swing with the mom, so her list of friends is exclusively older people that are friends of her sisters or brothers.

Apparently two years ago an older female friend of the family (22 now) was dating some guy (then 21) at an anime convention where all the daughters were brought along. The (then 14) year old developed a crush on this boyfriend. The relationship with the older girl and the guy only lasted about 8 weeks (apparently this is usually what happens for both of them). The 14 year old girl contacted him online, and started a friendship.

Things escalated at 15 when the boyfriend came to town to ask the mother if he could date her daughter. The mother, at the time, told him he could when the daughter was 17 (legal statutory rape law in this state). That being two years away, the mother thought the problem would just die with time. Instead, the daughter tried to plan secret trips to conventions this guy would be at, and spent endless hours talking to him online. The daughters plans to meet up using some random strangers from craigslist as a ride didn't succeed at the time. The mother caught on. Much drama was had.

Where I come back into this situation is that I'm an occasional guest at these sorts of conventions. I'm relatively close to the family, an adult (28) male, an upstanding citizen and a gentleman. She wanted to go with her older sisters and some friends. I was reluctant, but convinced when the mother was pushing for it herself. So I drove a teenager and her 21+ friends including her sisters out to a tiny convention. I was warned about the boyfriend. He basically hovered at ~100 feet the entire convention even after some words from the oldest sisters fiance about him following us around. He felt this was fine because it was a small convention and there wasn't much space, and the girl believes this line, but I base my judgments on some really obvious actual following going on. At points, we would leave a room and then he would. We would hang in the hall, and then he would. It did not stop.

There was drama and fallout after this. I confronted him a bit (casually, as an adult to an adult asking questions). I really tried to give him a chance, and it failed miserably. He's obviously really bad at understanding emotions, even his own. And he did not seem to get that his "true love" relationship was manipulative just in its nature.

Skip forward a couple months. They keep getting hot and heavy online. I know she once referred to them as "lovers." He breaks up with her because he "doesn't believe they'll ever be able to be together", and then rescinds his break up when she begs him to online. Now she's basically promising to escalate things more quickly. The daughter asked her mother again about dating. The daughter then tried to get the boys old girlfriend mentioned above to be a chaperon for a date at the mall for 10 hours. She tried to get me to give them a ride to this mall. If it had been just for what she said it was for, to spend some time with her older female friend, I would have agreed... but I knew something was up. I also noticed the older female friend was incredibly reluctant herself, and she cancelled anyway. Then the little girl asked her mother again if she could date him (because her secret plan failed, she fell back on the honest approach at least). Her mother then started getting angry about the whole deal and texted me.

I'm apparently having a conversation with just the mom tomorrow. She seems to think I have some ability to stop this, because of my dad-ing roll. All the daughters seem to look up to me at least a little bit, I guess. But I'm not really feeling like I can do much here. I've internet stalked the boyfriend a bit to get some idea of what's going on with him. He has very bad emotional control, some borderline traits, has admitted that "girls his age just don't want what he wants anymore", and even had a post about how high school girls are easily infatuated. He's also a 23 year old C/D community college student working at subway. There's just so much evidence, from my perspective, that he's a loser. But at the end of the day that's not here nor there, I guess.

So there is now a Romeo and Juliet situation, and I think I'm being asked to play Tybalt. At the moment, I want to advise the mom to treat her daughter more like an adult instead of a little girl. That's some obvious advice, but then things get into minutia and details where I'm uncertain.

Should someone talk to the boyfriend? Me? The mom? The mom's boyfriend? I've tried talking with him before... I feel bad because it always ends up turning into me talking down to him or about him. I feel like I know exactly what's going on in his mind as an adult male that has fooled myself about things before, so this just sort of happens.

Should the mother clearly communicate some rules? I think she should have been more direct earlier, and ruled out the level of contact they were allowed to have for the "before you are allowed to period." Instead, they have been emotionally intimate for over a year now. But escalations in rules are inherently temporary. Should she restrict contact in any way?

As a "dad-figure, but not dad", what right do I have to say or do anything? I have expressed my concerns to her. The main reason she is attached to me like this is because I just treat her like an adult like anyone else, but when it comes to the boyfriend she seems to think I'm "controlling" her just by telling her what I think of him. She has even called me a "liar" for mentioning some of the things I've seen in his youtube videos and blog posts. At some point after I told her some of the things I saw, he deleted his blog entirely.

Oy. The drama. Things were better when I didn't talk to anybody.

I'm thinking of trying to push the school angle again. Get her on a regular schedule so she isn't talking to boy-toy till 7 AM every day. Meet people her age. If she wants to date someone, tell her +/- 2 years is fine if chaperoned by her mom or one of her sisters. Since her slightly older sister is 18, I think they can reasonably go out together and both have a fun time and a safe time. I think the transition at 16 going on 17 going into public school will be difficult. I'll offer to help with tutoring and buying any necessary supplies.

No plan meets first contact blah blah blah, but this just seems to me like a very reasonable thing to bring to the table.

It's difficult, but teenagers respond better to being informed, rather than being told what to do. If they feel like they're being pushed, they'll nearly always go against you.

Does she know about the guy's post about High School girls being easily infatuated? That sounds a bit predatory to me. I don't like that. Was it as snidey as it sounds?

It was actually him making the comment as an observation of his past experiences. Then saying people need to get over it. So not snide, but still a bit of a double standard in context.

Either way, I think things managed to work out without my involvement. That's much to my preference. I'm not good with drama.

On this topic, just to vent a bit, I'm still dealing with the aftermath.

She told me she is following her mother's wishes to not date the guy, but stay friends with him. That's not precisely what "mom" wanted, but I'm trusting the 16 year old on this. Now I see posts by boyfriend guy on facebook being rather complaintive about girls in general, but they still seem to talk all the time on facebook. So I have no idea where things are going, but because I've promised to stay out of things, I will.

Bizarre update.

Apparently despite earlier statements, she's still continuing things online with this guy. I'm not sure what either of them expect long-term out of this. As I said, I'm trying to not be involved, but I'm aware of things. I learned this because I'm spending way more time with this girl. Why am I spending so much time with her now?

The school angle I mentioned before. Her mother forbids public school. For whatever reason, she's fine with me tutoring her sixteen year old daughter 10 hours a week (2 hours a day) in my apartment. This is weird, right? If I heard any other adult male was having a teenage girl over every weekday for hours, I'd assume bad things were going on. I'm not sure how I've earned this place with her, her mother, or everyone else. My schizoid asexual personality type thing must just be the most un-threatening male presence ever or something.

Either way, the tutoring is helping her. We've only been going for a week now and she is actually starting to get things done and to think about long term plans. I hope the momentum keeps going. Apparently she has absolutely no education on history or science, so those are two areas of focus. In addition, we are working on math while she still does home-school math with her mom at home. This is because her mother didn't want her learning algebra till college... so we are secretly studying math. I do find that hilarious, and if the worst thing I do is teach someone math...

I do sort-of wonder how things will go if we get to the "health and anatomy" portion of the science curriculum I've got. I know her mother won't touch those topics with a ten foot pole due to her terrible association with the topic from her childhood. Cross that bridge when I get there... I guess...

And apparently her "parents" are out of town next weekend and they want me and a few other people to check in on the family (both for normal reasons, and to rule out her sneaking off with/inviting over the older internet boyfriend).

School is going very well, I think. We are flipping back and forth between history and math mostly. I need to get her comfortable with saying her answers even when she's not sure if she's right, but I think that's just a matter of experience. She had some kind of harsh piano teacher in the past, and she is just afraid to do it wrong.