I give up. How great is this place? Is he just picking up chicks who want to live there?
I mean they all LIVE there? Nobody leaves? Do we all want to date Bob so we can move there? What’s the attraction? I doubt it’s Bob.
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You could approach the conversation w/the pastor’s mom like, “It was great seeing you yesterday. Looking forward to catching up with you. Give me a call when you’re free. I have a concern about something I’d like to run by you.”
and then when she calls, tell her your concerns about Bob and ask her advice on how she would handle it if it was her mom being courted/love bombed by a person behaving this way.
And then see what she says. 
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Or give her a call and say “Okay, spill.”
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And you just know that if the OP’s MIL does, in fact, marry this guy and move in there, the entire time she’s living there, everybody will be gossiping about her. The ladies will be courteous to her face, but there will be a palpable undercurrent of disdain just under the surface. She won’t be invited to participate in social activities. AND a lot of the residents who have seen his escapades in the past will look at the OP’s MIL as a couple of things: (a) Bob’s dumb next victim; (b) a gold digger looking to take advantage; and/or (c) the reason his prior marriage ended (even if she isn’t the reason, that’s what people will say, since he started pursuing her before the ink was even dry on the divorce papers).
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Or she’s just joining an elite club and will be the fourth at the dining table where everyone has something in common with plenty to talk about.
And honestly, maybe she doesn’t care a bit what anyone thinks.
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Unfortunately that’s the mil’s issue. It sounds like Bob likes to keep her close, mil might be ok with that.
@Hoggirl is really making a great discussion topic and I’m here for all of it.
My kid dated someone who had some big red flags. They also were a good person. My sibling warned my kid, my kid didn’t want to listen. My husband and I tried to be supportive because in the end it was the kids life and not ours to determine what they wanted.
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I think this is what it boils down to. You spend so much time trying to protect your kids from wrong decisions and then turn around to find out you are trying to protect elders from the same things. It’s like a hamster wheel you can’t get off!
Like does anybody ever live and learn? Or is that just a myth to aspire to?
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Oops, yes, the pastor’s mother. I hope that she won’t be as careful as a pastor’s wife might be!
Y’all shoot me if I ever come on here and talk about how I am falling for a four-times divorced/widowed man, no matter how nice his CCRC. Y’all know how I love me a good CCRC!
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I agree with all except b)
For all we know, he is the gold digger
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I think that’s entirely possible, but it’s likely your MIL is the one who will be called that. It’s usually women who get labeled that way.
That said, I see a lot of red flags here. I’m hoping she will continue to listen to your H about the finances. And I’m hoping she doesn’t sell her house and have nowhere to go if this falls apart.
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It definitely smells like it is Bob who needs a few $$. A divorce generally means one’s net worth takes a hit even if there is a prenup. A court would not toss an elderly woman penniless on the street and award everything to the spouse. So Bob must have taken some hits through his history of medieval behavior.
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I talked to my bff today, and I thought she had a really good piece of advice. She suggested that when dh talks to her he approach it as wearing two hats. “As your son, I want you to be happy, thriving, well-loved. If Bob is the one you choose, I support that. As your financial advisor/accountant (my dh is a CPA and does her taxes), here are things I would advise you (anybody) if you decide to marry Bob.”
There is an emotional piece and there is a practical piece. If he can present those in a bifurcated way, I think she will be more willing to listen
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LOL. Sounds like this starts “I love you BUT…”
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Yeah, maybe.
Ugh
Listen you can only tip toe so much. If your husband or other family has valid concerns or questions you just gotta put it out there. You don’t act angry or critical or treat her like a child but confront/converse with her adult to adult. Maybe not even mom/son - adult to adult.
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You might want to validate her excitement at being in love. Acknowledge that being courted feels wonderful. “It must feel really exciting to have Bob pursue you!” “Anyone would feel good being courted like this!” “Wow, he really is paying you a lot of attention!”
She will feel seen and understood, and it may make any subsequent conversation less difficult – especially the way you phrased it in Post # 432.
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I do think it may be important for your husband to stress that you guys don’t need the money/aren’t worried about an inheritance (I assume that’s the case), but that you are worried about her keeping control of her assets/not having them used by him to her detriment.
I doubt that she would go for this, but it might even be a good idea for your H to be given MORE control over his mom’s money, so there’s less of a chance of Bob taking advantage. And if she’s willing, then having whatever needs to be done set up sooner rather than later would be good.
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The idea of having a bifurcated discussion, starting with how happy and excited you are that she is enjoying being love bombed is a great idea and more likely to make her more receptive to financial cautions.
Maybe a LONG engagement would be a great thing. HAHA!
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Thanks for sharing Bobgate. We hope to read HAPPY and GOOD for MIL developments. 
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Actually, your H could say “I’m delighted as your S to see you happy and experiencing new things and being in a relationship you are enjoying.”
“As your financial advisor, I have to advise you to be careful to protect your financial future against any and all dangers—inflation, marriage, making judgments and decisions too quickly without working with me, etc. Any and all good financial advisors would be seriously flawed not to urge you to protect yourself as you could live a good many years more and need your assets to last for your care and enjoyment. You can even add that we ALL have to make sure our money will last our lifetimes as being poor in old age is just VERY unpleasant for everyone.”
This way, marriage is just one of the dangers.
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