Some Questions About My Son

Dear Windy, I have some questions about my son. One search led to another and I wound up on your site and saw your email address. You seem like a very nice person and I'd like to ask for your advice if you don't mind. Two years ago, when he was 12, I came home early from a date (single mom) and found him dressed in my clothes and smoking my cigarettes. I lost it and became hysterical. I grounded him for four weeks after I calmed down but we never really talked about it because we were both too embarrassed (or at least I was). I stayed home from work today to do a little spring cleaning. While cleaning up his room, I found several pieces of my clothing (bra, panties, slip, nightgown), two packs of my cigarettes (one was open), a lighter, ashtray and several wadded up pieces of aluminum foil filled with smoked cigarette butts.I didn't remove anything and I didn't tell him what I found. I was disappointed but I wasn't surprised. I had hoped this was a phase but apparently its not. I'm not proud of the way I handled the last situation. I haven't confronted him yet because I want to do better this time. I want to ask advice from someone who has been there and done that before I talk to him. I want to be more open-minded and compassionate than I was two years ago. Sharon

Dear Sharon, My heart aches for you and your son, but you have the opportunity to reach out to him and I'm going to try to help. I think of myself at his age, how I would have reacted if my mom found me out, and I guess the best thing I could have heard would have been something like this: "I've always been bothered by the way I reacted when I saw you dressed up that time. Please, let me finish: I've done some reading, and there is nothing wrong with wanting to experiment. In fact, I think it's kind of cool. Some day, will you let me help you dress up? You would make such a pretty girl, and I can help buy your own things, so you wouldn't have to try on my frumpy old clothes. Do you want to try it sometime, just for me?" He may try to pretend that he isn't interested, if so let it pass and bring it up again before Halloween. As for the smoking, I do think you should tell him how bad that is for him: you can distinguish between harmless dressing up and harmful tobacco. I know this will be hard, but if you wind up losing a son and gaining a daughter, you may help her find happiness. Chances are, your boy is like most of us, a straight hetero guy who digs the rush from dressing up like a girl, and if you can share in his joy from this, you will be closer than most sons and mothers can ever be. Windy