Dear Dr. Romance:
Maybe you can give me some advice. I am 18. 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?

Dear Reader:
You are a brave guy, to consider walking into this hornet's nest. I don't think you have to worry about your ex-girlfriend's mom wanting to have sex with you.  What worries me is what happens when her daughter finds out.  You could be caught in a really nasty dysfunctional family trap. But you didn't ask whether I think you should, so If you want to do it anyway, you're of age, so you can just offer her another massage.  If you move into the erotic zones with your massaging, and she doesn't stop you, then she's saying "yes."  Proceed slowly, and if she responds, and doesn't say "no" she's probably wanting to go ahead.  At that point, if you're not sure, ask her if it's OK with her to have sex.  If you do have sex, make sure you're using a condom -- you don't want to get caught in an even worse tangle than this one.  Read my article "What is a Dysfunctional Relationship" (see previous post) and please be careful -- situations like this can become very painful. Personally, I think you'd be better off reading It Ends with You: Grow Up and Out of Dysfunction  and finding someone more suitable

It Ends With You

For low-cost counseling, email me at

Author's Bio: 

Tina B. Tessina, Ph.D. is a licensed psychotherapist in S. California since 1978 with over 30 years experience in counseling individuals and couples and author of 13 books in 17 languages, including It Ends With You: Grow Up and Out of Dysfunction; The Unofficial Guide to Dating Again; Money, Sex and Kids: Stop Fighting About the Three Things That Can Ruin Your Marriage, The Commuter Marriage, and her newest, Love Styles: How to Celebrate Your Differences. She writes the “Dr. Romance” blog, and the “Happiness Tips from Tina” email newsletter.