Q. I am a 41yo separated male who has been "divorced" for several years in every way but legally. I posted a personal ad on a large site months ago and have been contacted by- and met- a number of nice women. There is one woman in particular that I am very interested in and have been spending a lot of time with. The problem? I have not told her I am still legally married and did not share this in my profile because I believed it would scare women away. 
The circumstances of WHY I am still married are complicated and have nothing to do with love or a desire to remain married. I am trying to do the "right thing" by my wife who needs my insurance for a medical condition. Even if she could get her own she would not be covered, due to a pre-existing condition. I have not shared her health issues or any of the problems we had with the women I have met, because I fear they will believe I left her due to these-, which I did not. 
As you can see, I have some baggage and now a secret I believe will ruin my new relationship. My questions are these- should I have been honest upfront about my marital status (in the profile)? How/when do I tell this woman the truth? I don't want to loose her.

A. Believe it or not, this is not the first time I have had a question like yours. Personal ads often contain less than truthful information and this is why folks need to not assume upfront that the other person is all they say they are. I am assuming that you and this woman have talked about yourselves and that she has asked you more information about your wife and why the marriage failed. This is a subject that comes come up after people have been dating for a while. If so, what did you say? If the answer is that you told more lies to cover the first- you have probably destroyed any chance of a relationship with this woman. 
To answer your first question, you should have been honest upfront in your ad. It is never a good idea to display too much baggage or offer too much "negative" information, however, a simple, …"separated for 2 years and not divorced only because of issues involving insurance coverage that we continue to work on resolving…" would be sufficient. Honesty goes a long way and can help to mitigate the negative aspect of being separated, not divorced. In addition, it speaks WELL of you that you are decent and caring enough to show concern for your wife's well being and have not abandoned her. How a man treats his first wife is a blueprint for the second marriage… 
At this point, all you have left to do is to come clean. Make a date to do something quiet- like dinner- where you can talk privately, and without interruption, etc. Begin with something like, "I haven't been honest with you about something that is very important, and I deeply regret my early decisions around this." Then tell her about your wife's condition and her need for YOUR insurance. Then let her know that this led to your placing a divorce on hold. Don't ask this woman for forgiveness. Put the facts out there and focus on HER and how sorry you are to have been dishonest with her and that you realize it could change everything. Let her know that you really like her and would like to continue seeing her, but you will accept her decisions around what she needs to do. Again, make HER feelings and needs the focus. Making this about you will just reinforce her negative feelings. 
Much will hinge on her reaction to your news and how she wants to handle it. Remember to follow her lead.

© copyright 2005, Antoinette Coleman. All rights reserved.