Relax. You might not have a problem after date #2 with each of them, because without sounding like negative Nancy, you might feel differently about one or both on the second date. I actually have a good friend who was dating two men for almost a year, and was honest and upfront about it to both guys. I’m not trying to make you feel badly about yourself, or feel guilty because you are doing nothing wrong. Jackie, I’m recently single and I’ve been in a relationship for so long that I forgot how to talk to women. This divorced dad needs some divorce advice: My ex mother in law let me have dinner with my kids while my ex-wife was working. By clicking on the button above, I confirm that I have read and agree to the Terms and Conditions and Privacy Policy. I will never forget having lunch with a colleague several years ago who had recently wrapped up a painful divorce.
My initial response was one of shock, and I asked, “Why would you want to date a man who has never been married before? Was it “better” to have someone who understood what marriage was all about and was familiar with all of the compromises, the peaks and the valleys?  Was it “better” to have someone who may likely already have children? At the same time, I think we were both astute enough to recognize that we were making complete assumptions based on stereotypes. At the end of the day, she said, she doesn’t have any preconceived notions about what kind of man she would most like to date. Over and over again, people dating tell me these nightmare stories about first dates and how it’s almost impossible to meet anyone normal, and how they’d give ANYTHING to find someone they even want to go out with on a second date.


Her now husband of 15 years and father of their three children ended up telling her that if she didn’t break it off with the other guy, he was done. What I mean is, I don’t think you will end up dating both girls for almost a year, but my point is that it is possible for a little while, until you figure out you don’t want to take things further with one, or that you like the other one so much that you choose to date only her.
I truly believe as you go on more and more dates with these women, the decision will be made for you. But I do feel compelled to tell you to do the right thing and be upfront, so if someone is going to get hurt, at least they weren’t deceived in any way. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues. Wouldn’t you wonder why he hadn’t married by age 45 or 55?” Now, I recognize that is very narrow thinking, but in honesty, that was my first reaction. What followed was a really great discussion about the perceived pros and cons of dating (or potentially marrying) someone who had never been married before, versus someone who had gone through a divorce.
Of course, we realized that every situation is unique, and every individual brings their own perspective to a relationship regardless of whether they are previously divorced or perpetually single! She said divorced or never married doesn’t matter to her.  She said ethnicity doesn’t matter. While we may have an idea of what is important to us, the reality is we that have to be flexible and open to having our preconceived notions change or we might miss out on meeting, dating, or even marrying, a really fabulous person!
Are they the really important factors, or just some preconceived notion based on stereotypes? Honaman wrote “The High Road Has Less Traffic: honest advice on the path through love and divorce” in response to a need for a book that provided honest, real, and raw advice about how to survive and thrive through one of life’s toughest journeys. Or, was it “better” to have someone who hadn’t been through the negative parts of marriage and divorce, someone who might not potentially be coming in with lots of baggage and chips on his shoulder?


I asked her if she had a preference for dating someone who had been divorced, or had never married. She said age doesn’t matter. What is important is sharing a common religion and having someone who can keep up with her active lifestyle! Would someone who had never been married be able to adjust to sharing his life with someone else? She pointed out that one’s prior marital status is completely irrelevant to the things she deems most important. I told her I would keep my ears open for someone who might be a great match for her!
If he had said he wasn’t interested in dating an older woman with two kids, we wouldn’t have just celebrated four fabulous years of marriage! One or both will sense it and pursue a conversation of exclusivity, especially if things start to get physical. The right decision will become clear (in my opinion.) And by the way, if things do start to get physical with either, I’d suggest not sleeping with both women. Wouldn’t you want honesty instead of investing a ton of time in someone, only to be dumped for the girl he’s been seeing since day one of your relationship?
Would it be difficult to adapt and compromise?  We didn’t have any answers, but we had a great dialogue about the perceived pros and cons. But, she did say as someone who has never been married, she wonders if men might assume that she is too set in her ways to change much if a partnership were to develop. She wonders if they question why she has never married.



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