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Notes -
A close friend (Bob) is considering proposing to his girlfriend (Alice). Alice is an ex-prostitute. I am trying to talk him out of it.
By Bob's account (which I presume in turn is him parroting Alice's account), Alice's stint in the oldest profession was a regretted youthful indiscression perpetrated in her teens, for a couple of months. She wasn't groomed, she wasn't coerced, she wasn't doing what she had to do to feed her starving family: she was just horny and kinky and thought it would be hot. After it proved less hot than she anticipated, Alice got out of there and never did it again, and since had the 'normie' sex life of a 21st century young woman: (uncompensated) app hookups interspersed with long term monogamous relationships, most lately Bob.
My gut-level revulsion at the prospect of wife-ing a ho makes my effort to talk Bob out of it difficult, as my churning viscera limits my rhetorical strategy from being much more sophisticated than, in so many words, just yelling "CUCK CUCK CUCK" at him. Perhaps with a side of "If you're not part of the solution for deterring teen whorishness by making it's practitioners persona non grata in polite society, then that's how you get more teen whores".
I am wondering if the astute minds of The Motte can help me think up any more coherent arguments to deploy.
So, separate a couple things out.
The fact that she was deviant and horney and naive enough to do this, is certainly a flag. "Youthful indiscression" is a bit of a euphemism or handwave or cope, because most youths don't make that kind of indiscression. I would be wary that this kind of outside-the-norm behavior is not some isolated trivia but representative of unreliable behavior traits that could be easily avoided in most other women. I'd be curious whether, aside from this she really is super normie now and what exactly that means. Sex norms and appetite vary widely with young women.
What's exactly her disposition now? Does she find prostitution morally wrong? (does Bob)? is this a repentance situation or a "not for me" scenario? These are very different starting points. Has she done actually 'work' to change? Has she had a transformative epistemic outlook, or was it more like, whoops! that went to far, etc? Would she disapprove of her daughter doing the same? If she's "reformed" and frames her past perspective as a moral failing and a cautionary tale, I'd probably leave it alone with Bob. Sinners deserve forgiveness. If she's still open-minded and women's choicy about it, but it's just not for her... I'd really talk Bob out of this one.
On a personal, disgust level, yeah I wouldn't personally be able to handle it. It's possibly worth mentioning that to 'normalize' the disgust reaction and give Bob an out to interrogate whether he's accurately evaluatoin his own. But I wouldn't take it to far.
In sum, the current nature of her today and her position on her past mistakes is super important to judge the context. Plenty of people are repentant of their past and it's good that they find people who can forgive them. Other people get fucked by overlooking severe lapses in discernment. Overall, I'd consider how she feels about prostitution in general today as more important than what's she's done in the past. Based on what you've written it's impossible to tell which is which here.
If forced to choose, I'd rather marry a hardcore born again trad-wife who stood firmly against sexual misconduct but had dabbled in the past and repented than a progressive minded virgin, who was outspoken about the right to sex work and rejected sexual prohibitions as patriarchical and unjust.
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