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The Strawberry Letter: I'm Trying Not To Run Him Away

Subject: I’m trying not to run him away

Dear Steve and Shirley, I am a 47 year old woman and I’m with a man that is out of my league. Don’t get me wrong, I have a great job and I’m educated but my past is sketchy. He’s a surgeon and his daughter just finished medical school. He’s been divorced for 6 years and he’s ready to settle down with me. We met on a site for professional singles and we’ve been dating for almost a year. I’ve never been married but I worked as an escort and lived with a man for 14 years. Some say he was my pimp, but I looked at it as a business that we ran together and we made a lot of money. During that time, I had a son by one of the guys I saw regularly. The guy found out he was the father and he filed for custody and won, because of my lifestyle. I have a good relationship with my son and I paid for his private school tuition up until he graduated two years ago. I want to share this part of my past with my new boyfriend but I do not want to run him away. I can’t get that time back that I wasted as an escort, but I made sure that I changed my life for the better. My new man and I have run into to my ex- pimp or whatever he was and I told my boyfriend that he’s an ex-boyfriend. In the past, my ex-pimp purposely destroyed a great relationship I was in, simply because he was jealous. I can’t let my new man find out that way. I have not even told him that I have a son. What kind of man will be okay with this? I feel like the longer I wait, the worse it will be. I have been in counseling because I don’t feel worthy of a good man like this but I know we all have skeletons. Do you think he will judge me and dump me?