GLO: If depledging were her choice, I'd try to find out why - maybe she was just uncomfortable with her original choice. If the chapter forced her to depledge (presumably for doing something sketchy) then I'd be more hesitant.
Employer: A lot of people move around a lot these days, and contract work is very common in my field, so I wouldn't hold it against a candidate, but I would expect to see references from at least a few different places. If someone were laid off due to an economic downturn, I would not hold it against them. If someone were fired for cause, I'd want to know the cause, and I'd consider how relevant it is to the job in question - e.g. if they were fired for embezzling and I were interviewing them for a job where they'd be handling money, I wouldn't hire them, but they might be ok in, say, a data entry job.
Fiance: If he told me before we got engaged, that he'd been married before, I'd be ok with it. Doesn't mean he has to tell me on the first date ("Hey, aephi alum, wanna go grab some coffee? By the way, I used to be married."
) But once the relationship started getting serious, I would expect him to be honest with me. If we were already engaged and I found out from someone else, he would be out the door.