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Dear Dolores

Dear Dolores: Does Mother Really Know Best?



Dear Dolores,

For the past four months, I’ve been seeing a wonderful, smart, funny man. My mother is worried because I’m 22 and he’s 32. He also has two small children from a previous affair and spent some time in prison. I understand her concern and anxiety—I do! But should that stop me from pursuing the first man I have ever truly loved?

Frustrated but Happy

Dear Frustrated,

I understand the appeal of a “bad boy”. Truly, I do. I would like for you to examine this attraction that you have to this man. Do you think that you changed him? Do you think that you can? When he has expressed his commitment to you, is he doing it because you are giving him or his children the support they need?

Understand your mother is concerned for your happiness, safety and well being. She is older and has presumably been around the block a few more times than you have. She does not want you to be unhappy and her concern is coming from a place of looking out for the most important person in her life. 

I have been on both sides of the criminal justice system as a defense attorney and as a judge. I believe that people can change and be rehabilitated. However, the words “affair” in the same breath as “prison” lead me to believe that his man has made some dumb ass choices in his past and may be looking to you to be some kind of salve. That is not your job. If he is a good partner to you, great. You clearly have some hesitations or you would not be writing to a stranger for advice. Ask yourself the hard questions. If you are still on the fence, take a step back and ask yourself if this is what you want in a partner.

Love, Dolores

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