Monday Madness: Can I Date my Ex-Wife's Sister?

Dear Everyone Who Matters:

Today I will attempt to answer a question from a reader in rapid fashion, for two reasons:
1) I need to write quickly today, as there are only a few hours left in Tucson, and
2) I have had repeated complaints that my blog is too long.

Here we go!

Dear Robin:

I have been divorced from my wife for 3 years. It was a very difficult divorce and my children are finally starting to get over the pain of losing their family (I have two grown children). My ex-wife’s sister Jane is also divorced and recently she contacted me on Linkedin. She is looking for a new job and I know some people in her industry. We met for coffee and then drinks a few days later. Since then, we have had dinner a few times and it is clear there are feelings between us.

Robin, is it OK for me to date my ex-wife’s sister? We’ve always gotten along really well and I feel a strong attraction towards her. How do you think I should handle this?

-Ed in Boston

Dear Ed:

Please don’t take this the wrong way, but people like you are why we have signs like this:


Can you date your ex-wife’s sister? Sure. Should you? Um, that would be a fuck to the no.

Let me spin it out for you so you can see what your future looks like should you go down this path:

1. Your ex-wife will basically shit her pants in fury and any hope of you two having a decent relationship in the future will be lost.

“But Robin,” you cry, “why does that matter?” Well, Ed, if you really must be drawn a picture, imagine your kids’ weddings, grandkids’ events, etc. Don’t they look lovely? Isn’t it wonderful to see your children as adults and then watch them raise children of their own?

Oh wait, you aren’t invited because you decided to stick it in Aunt Jane. Your ex-wife certainly has ample material to make hay here and get you cut out of all future family events, or at the very least make them exceedingly uncomfortable for you, which in turn means uncomfortable for your kids.

2. You and Aunt Jane will be in the most unenviable position of having to constantly defend your relationship as well as convince people that nothing was going on while you were both married. Good luck with that. Having gone through that myself with someone whom I met after his divorce, I can tell you it is no fun to be whispered about and have the timing of your relationship speculated upon.
And yes, I know I just violated a grammar rule.


3. Not only will you cause a major rift between you and your children, you will also cause a major rift between the kids and their aunt, while also creating a family drama that will play out during the length of your relationship with Jane and long after it has run its course. And run its course it will, because relationships are hard enough without all this extraneous bullshit thrown into the mix.

You may be suffering under the mistaken impression that Jane is “The One,” and therefore worth all this trouble that will ensue should you insist upon dating her. She isn’t. You know why? Because there isn’t just “One” out there for each of us. That is a crackpot theory developed to sell romance novels and to convince utterly unlikable people that they are only single because they haven’t found The One yet.


Ed, you live in a big city with plenty of single women. Stop what you are doing with Jane NOW and go meet someone else. Ask yourself how you would feel if your ex started dating your brother. It’s gross, right? So knock it off!

I’m going to throw this out there: you should do some deep thinking about why you would even consider this course of action. Perhaps you are harboring intense negative feelings towards your ex and you know that dating her sister would be the ultimate payback. Unfortunately, while I generally support revenge and bridge-burning for those who have transgressed against us in significant ways (and I know from our email exchange that you have much to be angry about), in your case I must advise you to stand down.

Why? Because the intended target of your anger will enjoy an elevation in her Victim Status, and the true damage will be collateral to your kids. It’s just not worth it. I suggest you try, and stay away from people who share DNA with your ex.


This Post Has 5 Comments

  1. Autofocused

    Ed, Quickly get up and walk to the nearest exit. You will thank me soon enough. You’re welcome.

  2. Raftman

    This is like a line from that classic “Bad Idea Jeans” – SNL skit…..”my friends all think it’s a bad idea, and I’m not quite sure how it will go over with the kids, but I’m going to date my ex-wife’s sister…..” It would be funny if it weren’t so scary.

  3. Melinda DesCamp

    I gotta wonder what kind of woman would date their sisters ex. I’m more curious about how potentially fucked up she might be in the head to even entertain the thought. He might be a great guy but I think anyone can see that she shows a scarier lack in judgment than he does…..that’s her blood for Pete’s sake. Some things are sacred.

    1. askdescamp

      Good point. So I guess I should climb off my sister’s ex now?

      1. Melinda DesCamp


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