Should I allow him to date a girl whose mother may or may not approve?

A female age 51-59, anonymous writes:

My 16 year old son (junior in high school) is dating a very nice 16 year old girl. The problem is her mother does not know. Quick history: during their freshman year, Kevin and Lindy, dated briefly. The mother was aware of the relationship and very friendly towards Kevin. Kevin broke up with Lindy and began dating her best friend. Breaking up the girls friendship. This girl later broke up with Kevin and he again began dating Lindy, apparently without Lindy's mother's knowledge. Kevin tells me, that the mother hates him for originally breaking up with Lindy, and dating her best friend, ruining their friendship. Now Lindy does not tell her mother she is going out with Kevin. As Kevin's mother, what is my responsibility, should I allow him to date a girl whose mother may or may not approve. Do I interfere, get involved and actually contact the mother.

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A female reader, Teacake  +, writes (25 November 2008):

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