Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?
This is your opportunity to ask questions. No question too simple or too silly.
Culture war topics are accepted, and proposals for a better intro post are appreciated.
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Notes -
Convincing in matters of the heart is always hard. I might recommend posing some pointed (read: leading) questions:
"If Alice was so nonchalant with her sexual autonomy/privacy/choose-your-word when she was younger, what made her change?" You're looking for a discrete response with a very concrete experience-evaluation-decision-value update cycle. If Bob gives a wishy-washy "oh, she got more mature. She grew up" Press the issue.
You say "After it proved less hot than she anticipated." Assuming this is faithful reporting (I have no reason to believe it isn't, I'm just highlighting that this is an assumption) ask Bob, "How important is 'hot sex' to Alice? Pretty much every study on long term relationships shows that passionate love declines rather steeply, especially after marriage, and couples make-or-break based on companionship and shared values. What's the risk of Alice losing interest?"
This would get deeper and open up a larger can of worms and would, frankly, risk your relationship on the spot with Bob. However - "Bob, we can both agree that teenage self-prostitution isn't a normal thing. What do you think caused this, and what other less-than-common behaviors is Alice prone to?" You can see where this leads ... it's asking if Alice has a history of bad decision making, potentially some mental health issues, maybe even SA trauma from childhood (caveat, of course, those are all generalized "maybes" I am not saying or even forecasting that this is the case with Alice, but that would be part of the discussion).
Suffice it to say, both you and your buddy in deep waters. The best thing you can do is remain honest yet compassionate. Avoid "I told you so" if it comes to that in a few years. Avoid "Fine man, whatever" in the next couple of months. Be there for your Bro, Bro.
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