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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 leaving aside the arguments about whether you should do this, here's how I think one would approach doing it. (I always enjoy @Walterodim 's opinions on personal matters, and think you should seriously consider what he said)
You aren't going to rationally argue him out of this decision. You're at a distinct disadvantage: she is sleeping with him, you presumably aren't. And hey, even if you were, my buddy quit cooking because the hours for a chef were terrible, but he's still a hell of a lot better in the kitchen than I am. Marriage is an extremely serious and sobering choice for any male. If he's taking this seriously, he's already thought about all this. If he isn't taking it seriously, well, what are you really protecting Bob from anyway? He'll just get got anyway, a fool and his money etc.
I've never seen anyone successfully argue someone out of a relationship rationally. Women tried it on me some years ago, it didn't work. I've tried it on friends. Didn't work. But what did occasionally work is slipping a meme into one's conversations about the partner, that slowly eats away at the relationship. Create a conflict and feed it until it goes.
My buddy has bad taste in women, historically. He dated a truly crazy woman, she was five years older than him, picked him up at a bar, had been arrested twice for domestic violence (it wasn't her fault it was her BF's, yeah sure, the cops definitely showed up and arrested the 5' blonde girl over the puerto rican guy...), her ex bf still had all his bills mailed to her house, got in trouble at her sales job for showing everyone photos of her labiaplasty, etc. Just a real peach. The capper of it all was when she accused us of being gay together the first time I met her. I told him she was nuts, he didn't listen, they went on a resort vacation together and he wound up wandering the resort in his underwear after getting into yet another drunken argument in the middle of the night. All my rational arguments achieved nothing.
On the other hand, he once dated a girl, I didn't really like her when I met her. He asked me my opinion of her. I said she was like pound cake. Tasty but just fine, you'll eat it if it is there, but nobody's favorite food, nobody LOVES pound cake, they just eat it because it's around. This ruined their relationship. We started calling her "pound cake" in our conversations, he started thinking about her like that, the relationship was dead. Reread everything Scott Adams wrote about Donald Trump in 2015-2016 (he's since gotten even weirder, but his early stuff was interesting); read about Trump's application of OODA loops here.
What you need to do is drive a wedge between them, throw an Apple of Discord into their relationship, create a bone of contention between them regarding the marriage. How you do this is up to you, I know nothing about either Alice or Bob, so I realize I'm kinda riffing off my own relationships and social circles in this example, but here's what I'm thinking:
Talk to Bob about his impending proposal, and talk to him about a Pre-Nup, and about structuring his assets to protect them from Alice in the event of divorce or in the event of Alice facing major liability. Idk how bright Bob is, if you think you can pull it off try to tie the past in and persuade him that Alice could face some kind of legal liability for things she did, and that he needs to make sure that their assets are separate for that purpose, to protect them both. Provide examples of spouses losing their assets after one spouse gets busted, and bring up, ever so gently, that even though you absolutely love Alice she does have a criminal past, and you wouldn't want to see either of them run that kind of risk, after all if she were to face that kind of civil or criminal liability it would be better for both of them if he had assets to use to protect himself and her, so even though you adore Alice it's so important that he protect himself from the possibility of her past dredging itself back up.
If he won't fall for that, or in addition, try to tie in the past by bringing it up as an example of how Alice can be impulsive and mercurial, you love Alice of course and hope this never comes up!, but you are first and foremost Bob's friend and it's your job to give him advice, and part of that is making sure he's making clear eyed decisions and you won't let his or your judgment be clouded by how much you both love Alice. You want to emphasize that you have nothing against Alice, you just want to be realistic about the many possibilities in a long future together.
It's important he protects himself, it's standard for men like him, and one can never know how people might change over time, you adore everything you know about Alice but people do change... Bring up examples of people who made sudden life changes, and how it shredded their spouses. I'm thinking of my neighbor, a doctor, who got some kind of brain tumor that pressed on his prefrontal cortex that caused him to suddenly abandon his family and knock up a nurse two years older than his son. The new girl sent his son a letter, at the father's urging, offering to abort the baby if the son didn't approve. That fucked with the poor kid's head so bad that he wound up dropping out of undergrad. I'm sure you have someone like that in your mutual circles with Bob. Bring that up: you never really know who you're marrying because the person you'll be married to ten years from now will be different than the person they are now. Hell, look how different we are than how we were ten years ago! Which will lead his mind naturally to thinking how different Alice was some years back...
Emphasize that as long as there's no divorce or liability problem, it doesn't matter anyway, so if she isn't intending to divorce Bob it won't matter anyway, she's only harmed if she leaves him! Try to portray the prenup as a standard thing for men like him, just a normal thing to do, and contesting it as the odd and notable thing. Implicit is that if she balks, she is plotting to divorce him. You want to plant that thought as deeply as you can, without ever under any circumstances saying it out loud in a way that he could attribute to you. You're trying to do Inception here.
Best case scenario, she balks, and in the ensuing argument over "Why would you need this protection when we're never getting divorced, Bob!" Bob drops the "Look, I love you, but you used to be a hooker, you've changed before you could change again..." bomb, and they never recover. She attacks you for putting this in his head, but because you have emphasized how much you love her it makes her look petty and antagonistic, like she's trying to separate him from his friends, a classic tactic by manipulative abusers. He talks to you about it and you say, hey, I love Alice and I'm sure she's not scheming and evil, but you have to stand your ground, brother!, or you'll be in for forty years of this. Alice is great, but that doesn't mean she can walk all over you dude! You have to stand up for yourself!
Risk of a worst case scenario, she calls his bluff and signs it right away, cementing her position in good faith, and making you look petty and antagonistic, certainly painting a target on your back for Alice. But still a lower risk than if you tell him that he shouldn't marry Alice to punish her for her past sins.
It doesn't have to be the prenup thing, maybe it's moving to Bob's hometown, or it's career questions, or it's differences in childrearing or politics or religion. But you need to start a fight, where Bob is absolutely certain he is right and just doing what needs to be done, without directly attacking Alice because you will lose to the girl who is sucking his cock.
Great post, it's like Sir Humphrey but for relationships: you have to get behind someone before you can stab him (or her) in the back.
It's a George Costanza move for sure.
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