Should I Have Sex with My Ex?

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DEAR MIDLIFE BACHELOR: We were married for 27 years, have 4 children together, traditional marriage, separated for two years, and now are currently divorced. He is a highly functioning narcissistic alcoholic. I have not had sex with anyone (but myself) for over two years. I’m still fit and he says a hotty, just too busy for a relationship right now. He (ex spouse) and I are on relatively good terms for the kids sake. He wants to have sex with me. He called it “friends with benefits”. I just want to have sex with someone who is “safe”. Why not him versus a stranger? All the other men I’m attracted to are married. My only concern is that either of us would get emotionally
sucked in and start some of our old addict/co-dependant behavior when we should be continuing to break away from each other. I really would like to have sex with a man. Should I do it? What do ya think? Cindy

MLB ANSWER: There are two competing points-of-view here. The first is YES, you should have sex with him … precisely because he is safe, because you know what he likes/dislikes, he is familiar to you, he knows what your needs and preferences are, etc. It is an easy choice to make – one without many unknowns. Plus it fits with the ALWAYS GO FOR IT motto of ha ha ;o)

The competing point-of-view is – maybe it is better to keep him in your rearview mirror, and not have sex with him. I don’t know what your marriage was like – and I don’t know how it ended. You alluded to drinking and codependent behavior … so really you have to think about what having sex with him would mean to you in your own head, AND what the potential consequences are for both you and for him. For example, would he be scratching at your door several times each week if you now have sex with him? Did you have a hard time getting him to stop coming around when your marriage ended? If you have sex with him now, what do you expect his behavior to be like in the near future, and will you be able to deal with it? I usually tend to think worst-case when contemplating this sort of stuff – but that’s just me.

Now let’s say that you think having sex with him could potentially cause too many problems. In that case, you might instead apply this energy you have toward taking the steps necessary toward finding a new boyfriend. Dating is not easy – there is a lot of trial-and-error involved. And after a while, people typically find it to be a tremendous personal growth experience. In other words, you’ll never find yourself a new man unless you make a concerted, proactive effort to start looking and dating … and there is no better time than the present!

If you would like some ideas about jumpstarting yourself back into the dating scene, then check out the following sections here on’s Dating Advice section. They are all written from a man’s viewpoint, but can apply toward women – you’ll understand as you read it:

Midlife Bachelor Personal Makeover – fine tune your appearance and your attitude so that you can more easily attract someone

Develop a Strategy for Midlife Bachelor Success – leverage your personal strengths, set achievable milestones, and do the things necessary so that you attract the type of person you really want.

We also have an excellent Midlife Forum here where both women and men discuss various dating situations and issues. You are not alone in your situation, and we would be happy to have you as part of our Midlife Forum community. Good luck – let me know how your efforts progress!

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.