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Although I enjoyed reading this and enjoy rubbernecking at a potential car wreck as much as anyone, what's the point of staying in touch with her? It seems she provides mostly idle amusement and the possibility of future sex. It also seems to have some outside risk of blowing up in your face--e.g. ruining a hypothetical future relationship that does have real potential. If it's primarily charity, then there are millions of other recipients who would likely benefit more from your ministrations with a much lower risk profile.
A fair question to ask. I do it both because I'm bored, and because I genuinely enjoy helping people. I feel bad for her, she lacks the kind of agency that most people on this sub takes for granted. I genuinely don't know very many stupid people in my personal life, it's amazing how much good looks and money can cushion you from the consequences, right until it doesn't. She lives her life in a daze, circumstances seem out of her control, everyone seems nice, but they're often just lying through their teeth to get into her pants. Someone who was smarter would confidently wrest that to their advantage, she just suffers. I suppose that's why she likes me, I'm one of the few men she knows who never lied to her, or stopped treating her kindly when she had nothing left to give. (The bit about getting laid next time I see her is mostly in jest, I'm a red-blooded man with no serious objection to sleeping with hot models, but I'm not going to go out of my way to achieve that)
The most influence she plausibly has over her life is her choice of partner, and giving her some advice doesn't cost me much.
All they have to do is ask. I try and help just about anyone who does, male or female! I'm not quite Captain Save-A-Hoe, but I know my tendencies. Am I drawn to broken people, or are they drawn to me? God only knows. In my day job, the answer is clear.
I'm presently single. Just like last time, it wouldn't be very difficult for me to cut her off should that change. In the meantime, I would genuinely be happy for her if she did find a nice guy to settle down with, she's not a bad person. I will probably wrangle invites to the wedding, God knows I miss hitting the buffet line at the Big Fat Indian ones now I'm away. It would be very funny, if nothing else.
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Fuel a sense of superiority. Won't lie, I was guilty of rubber necking in the same fashion when I was in my 20's. You take the short path, lock down your education and career, it's a good feeling. But your peers might have taken the short path in other aspects (family, investing, home ownership, etc). It compensates for the lack of other life milestones in those other areas.
Oh, I definitely did the same thing in my 20s. Sooner or later, though, you end up with that hot fling you stayed in touch with breaking into your condo and threatening you with a handgun unless you get back together with her. Which teaches a useful lesson, but it may be one of those lessons that can only learned by direct experience.
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