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From the sound of it, no, you shouldn’t. I think by the time you reach 50 and have been married 20 years once before you should know the answer yourself already. You probably do but don’t want to admit it to yourself. If you do go ahead with it you should at least have a pre-nup so you don’t get taken to the cleaners a second time. Unless by “ended badly” you mean your ex is buried in a Rubbermaid tub under the crawspace of your house, in which case you probably have bigger problems than deciding whether or not you should get remarried.
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