Hey Dan & Jennifer:

My relationship with my girlfriend ended with her leaving me. She said that we could remain friends. This happened over a month ago. My ex-girlfriend and I have remained friends. She has a new boyfriend and she seems happy. I am happy for her. We still see each other as friends and I am still invited to her house. This question involves her single mother. From dating my ex-girlfriend I have gotten to know her mom well. She is a very nice woman and very attractive. The other night I was invited by my ex-girlfriend to a dinner at her house. She, her new boyfriend, myself, and her mother were there. Her mom cooked. It was a nice meal and a fun time. After the dinner my ex-girlfriend and her boyfriend left for their date. I offered to stay and help clean up. Her mother was happy for the help. After we got done cleaning up the kitchen from the meal I asked her if she would like a massage. She said “yes”. I gave her a good rub down. It seemed to relax her and she seemed to enjoy it very much. It also gave us a chance to talk more which I enjoyed. I also enjoyed the feeling of her warm and smooth skin. After it was over she thanked me with a passionate kiss I would really like to have sex with her.

Do you think there is a chance given the fact of the difference in our ages and the fact that I was a boyfriend of her daughter? How can I let her know of my desire? Perhaps asking if she would like another massage would give us a chance to talk about this. How can I make this request to her?

Looking forward to your reply. Regards, Jake