Dear Miss A,
Firstly, I love your column and I read it daily. I enjoy the insight you provide as a result of a well-lived life.
Now onto my question. I am 30 years old and just out of a long term relationship. I am beginning to date again. I am also divorced. I got married young and divorced young. This was several years ago. My question is: How long do I wait to tell a date that I am divorced? What is the best way to tell him? I know this is a deal breaker for most men so I’d prefer to be upfront, but it doesn’t seem natural to sit down for dinner and immediately blurt out that I’m divorced. It may not seem natural to me, but it might be the correct route. I don’t know. I also do not want it to look like my divorce is something I obsess over. It’s in my past, not my future. I’m not sure how to balance this situation. Your advice is appreciated!
Divorced in DC
Dear Divorced in DC,
Men I’ve dated have been very understanding about my marrying young, and being divorced. I don’t think divorce is as much a “dealbreaker” as it is a nice excuse if a guy isn’t really that into you. Right after my divorce, I used to struggle with the question of when to “confess” that I was divorced. Telling the guy on the third date felt like the right time for me. (Please note that I think you shouldn’t see a person more than once a week in the early stages of dating, so the third date would give you three weeks of dating. He should be planning dates in advance and staying in touch with you on a consistent basis.) I think by then you can usually tell if the relationship is going somewhere. If it’s not going anywhere, then there is no need to open yourself up. Now that I’ve been divorced for six years, I’m much more comfortable with being divorced, and don’t stress about a guy finding out I’ve been married. Also, I’m in sort of a unique position in that for better or worse, my life seems to be an open book here in Washington, so most men already know my history.
After you tell the man you are dating that you are divorced. He will inevitably ask whether you have any children. I think it’s much easier for a man to accept a divorced woman when she doesn’t have children from her first marriage keeping her linked to the Ex. You didn’t mention children in your question, so I’m assuming that you don’t have any, but if you do have children, you may want to wait until the 5th date so that the man you are dating has an opportunity to get to know you as a person before dropping that bomb shell. He’ll inevitably weigh how much he likes you and how attracted he is to you against the fact that you carry “the baggage” of being a divorced mother. This will also give you more time to assess if he’s worth dating, and worth opening up to.
Remember, at least you had a real relationship, and gave it your best effort. From dating in Washington, I have learned that so many men and women in DC seem to go through the motions of dating and having casual sex, but never have a real relationship. They make it into their 40′s without ever having lived with or married anyone. What’s worse? Being divorced or never having tried? As Alfred Lord Tennyson said, “‘Tis better to have loved and lost than never to have loved at all.”
- Miss A
Andrea Rodgers is a Dating & Relationship Expert for HealthCentral’s Sexual Health Connection. Email questions to missa@askmissa.com.






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I totally agree, I myself having been in this same boat..”when is the right time to tell” and for me I am usually just very open about it. I guess I should say I am very open about it NOW. I’m 3 years post divorce and it’s firmly in my past and I’m very OK with that.
I also believe that it sets the stage for the conversation of “Oh, so your looking for the next Mr. Right?” This seems to be the question I get most frequently. I guess they (men) assume that since I have already been married that I am looking to rush back into another marriage and I think thats the biggest piece of information that I wish men knew/understood. Just because I made choices early in life doesn’t mean I have any intentions of rushing into a situation that isn’t right.
I guess all I am saying is that it seems to be a delicate topic and one I completely understand. Good Luck and just know there are quite a few of us “young divorcees” around the DC area.
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I don’t agree with mentioning you have kids until the 5th date. That should come out pretty early. If a woman waited until the 5th date to drop that, I’d be annoyed. Her status would change from a serious interest to casual sex. Who wants someone else’s baggage?
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