The word 'philandering' often suggests disapproval and moral judgment of the behavior. The community looked down on him for his philandering ways.
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Gender-specific
'Philandering' is traditionally used to describe a man's behavior, not a woman's. He was known as a notorious philanderer.
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Implies deceit
The word often implies that the man is deceitful, especially if he's in a committed relationship. His philandering was discovered when texts to another woman were found.