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I have trouble understanding the last sentence which reads "Are you sure you wouldn't be happier with a man who is making more money than you?"

Could anyone paraphrase this sentence in plain English?

Today, a successful single woman who falls for a man making less money than she does or not sharing her career ambition may face not-so-subtle disapproval from friends and family... Another felt insulted when a trusted friend asked, "Are you sure you wouldn't be happier with a man who is making more money than you?"

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The clause "you wouldn't be happier" is implying that the person believes they are happy in their current situation and that the alternate situation is not likely to make them any happier.

One could rephrase the question as

If you were with a man who was making more money than you, then you do not think you would be happier than you are now?

This is somewhat cultural where men are considered to be the "earners" and women the caretakers of the house/children.

Other scenarios this can arise, though are in work:

You wouldn't you be happier in a job where you earned more money?

Or, if coming from someone who enjoys being a parent and is speaking to someone with no desire to be a parent:

You wouldn't be happier with children to carry on your legacy?

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"Are you sure you wouldn't be happier with a man who is making more money than you?"

The person addressed is apparently happy with her man, who does not earn more than she. The speaker is suggesting that she would be happier with a man who earned more than she, by asking if she is sure that would not be the case.

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