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Is he pushing the marriage issue or is she?
If she's pushing it, then that should throw up a really bright red flag, and if he's going along with it, it could be because he doesn't want to lose the company of a young woman which might happen if he says 'no'.
If he's pushing it, he needs to ask himself why she is accepting.. What's the payoff, other than the obvious?
Have him mention a prenup to her and see how she reacts..
Lots of common sense questions could be asked, and the answers would be obvious.
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