My Boyfriend Still Talks to His Ex-Mistress. Should I Be Jealous?

My boyfriend and I are both in our mid-40s and divorced.   We have been dating for 5 months and were friends for 5 months before that.  

Two years ago, when he was married, one of his staff, who was 17 years younger than him and engaged, invited him to a hotel room and so began a 5 month affair.   She broke it off with him to marry her fiance.   My beau was devastated and left his marriage.  

I met him a year  after the break up with the mistress  and he was still very much in recovery mode over this young woman.   I don’t think it helped matters that she stayed in touch with him and would invite him to lunch and coffee on occasion.  As I got to know him, he seemed to finally recover and then we started dating.   But right at the beginning of the dating phase, I told him I would not get involved with him if he was still in contact with his former mistress. It made me uncomfortable.  And for 3 months, he wasn’t.

But  the former mistress (who thankfully now lives an hour away)  was in town and  invited him to lunch about a month ago.  My beau  decided then that he wanted to maintain a “casual intermittent” friendship with her.    I  had been  upfront with him in the  beginning that I wouldn’t be comfortable with this so an argument ensued.   He assures me that he is crazy about me and feels nothing towards her  and I believe him.    He says it’s a no big deal  friendship – to which I pointed out that her husband and baby  would probably feel differently (he knows nothing about her affair).    

My guy really is a great boyfriend and has been so good to me.   So what to do?    Why am I still so  uncomfortable about this “friendship”?       

Thanks!!!

Jeannie

Dear Jeannie,

I’m on your team with this one. And I’m struggling with it.

Because there’s this voice in my head that says, “Trust is the basis of any relationship. If you can’t trust, you should get out.” But I don’t think you should get out. And I don’t think you should tolerate him being friends with his former homewrecker either.

Now, I’m all about letting people be. Call me a social libertarian, but I’m pretty much always going to side with the person who is asking for more freedom. If he likes to flirt, he’s going to flirt. If he likes to do drugs, he’s going to do drugs. It’s not your job to change him. All you can do is determine if you’re willing to put up with his behavior. And if you’re not, you’re well within your rights to leave.

But this situation strikes me as something more specific and insidious. Because you’re not trying to stop him from seeing his drinking buddy. You’re not jealous of his cute, young assistant. You’re not trying to keep him away from his ex-wife, with whom he shares custody of his child. You’re merely trying to keep him away from the very woman who (with his consent) RUINED his previous relationship. Not only should you be uncomfortable, but the mistress’ unwitting husband should be as well.

You’re merely trying to keep him away from the very woman who (with his consent) RUINED his previous relationship.

And as much as I’m always going to tell women, “Don’t tell men what to do. We don’t respond to it,” I think you need to lay down the law on this one. Because, while it’s nice to trust, it’s also silly to leave your keys in your car….

If this is, according to your boyfriend, a “no big deal” friendship, it shouldn’t be that hard for him to let it go. Both he and she should understand why you feel this way, and you shouldn’t have to make a federal case out of it. However, if he doesn’t agree to give the mistress the boot (and if he cares about you, he should), you have some serious thinking to do. Do you tempt the fates or pull the trigger too quickly?

If this is, according to your boyfriend, a “no big deal” friendship, it shouldn’t be that hard for him to let it go.

I don’t know, and I hope you don’t have to find out the hard way.