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Dr. Lovemonkey: Cross dressing and criss-crossing with exes

Dr. Lovemonkey answers your questions
By DR. LOVEMONKEY  |  July 14, 2009


Dear Dr. Lovemonkey,

I'm a 48-year-old man who is a closet crossdresser. I love to dress and take pictures of myself in women's clothes. I've joined some free CD Web sites where you can correspond with other CDs through private messaging as well as post pictures. I want to meet and get together with other CDs in the area. How can I do this in a safe way and be sure I'm meeting with someone who enjoys my fetish and isn't a little bit on the crazy side? How safe are these Web sites and/or posts like the ones you see in "Flipside," which is in the Phoenix?

Worried CDer

Dear Worried CDer,

The fact is that any time one is engaging in sharing information and communicating on the Internet, there is an element of danger, and the Web adds another element in the sense that it provides a greater ability for people to be anonymous. I have no information nor data indicating that crossdressers who are active on the Internet are any more inclined to be "a little bit on the crazy side" than anyone else. But the fact is that virtually all Web sites and posts carry a certain element of danger. There is so safe place in the cyberworld, so always be cautious with whom you talk to and what you reveal.


Dear Dr. Lovemonkey,

I am a 28-year-old woman who, in the past year, has been able to lose 60 pounds. I am feeling good about myself and looking forward to getting into a relationship. Recently a good friend of mine fixed me up with someone and we went out a couple of times. The problem is that I'm not attracted to this guy at all. He has called a few times and has also emailed me. I really don't want to hurt his feelings and I'm also concerned that, if I blow this, it'll be a long time before I will get together with anyone. What should I do?

In Turmoil

Dear In Turmoil,

Nobody likes to hurt anyone's feelings, but you are not attracted to this person. So just tell him that you're not interested in seeing him anymore. You are young, good things are happening in your life, and you shouldn't be feeling the desperation that you seem to be experiencing. Things can only get better and, since you know that this person is not for you, just move on. He'll get over it quicker than you think.


Dear Dr. Lovemonkey,

This is a weird situation. I have been going with a great guy for two years and we are talking about marriage. He lives with his parents, but his ex-girlfriend, who he went out with for six years, also lives at his parents' house. Although I know that he doesn't have any sort of romantic relationship with her anymore and that he has been constantly true to me, it is awkward to say the least. She has been living there for a few years now. It seems to me that I can't make demands on his family about this, but what can I do?


Dear J.M.,

Yeah, this really is a weird situation. All I can say is that, after two years, you should have a pretty good idea of what your boyfriend is like. You should talk with him about your discomfort with the situation but, ultimately, if you believe in him and love him and are convinced that he loves you too, you'll just have to live with the situation.

Related: Dr. Lovemonkey: Burned and Brrrrr-ed, Ask Dr. Lovemonkey: Politenessman, Dr. Lovemonkey: Trouble calling, More more >
  Topics: Dr Love Monkey , Culture and Lifestyle, Relationships, Relationships,  More more >
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