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

jealous girlfriend

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”?       



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.


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  1. 21

    Well I am in the same boat as Jean only worse in my opinion………My current boyfriend of 3 months not only talks to his ex, but she comes to his house to bring him dinner.

    I have told him I don’t want them to be together but he insists he cares nothing for her and they are just friends. She calls all the time and is always around. They live 5 minutes away from one another. Im am 20 minutes away. This makes things hard.

    Even worse our children (mine and his) know each other and love spending time with each other. I don’t want to hurt the kids but Im not sure I can deal with her being in his life. I am just finding out how involved she truely is.

    He says he loves me and has asked me to marry him but I have to wonder if she will go silently away.

    Any advice would be greatly appreciated……..

    Sorry about your breakup Jeanne, I hope mine doesn’t come to that

  2. 22
    Karl R


    I’d say your position is not worse than Jeannie’s for one major reason: you didn’t mention any history of infidelity.

    Your boyfriend may be completely honest in saying that they are “just friends”. However, it seems likely that she is trying to win him back. He probably enjoys her friendship. I’m sure he enjoys the free meals. But he doesn’t seem to be putting any effort into the relationship. She’s doing the calling, visiting and cooking.

    You might want to sit down with your boyfriend and get some information about who initiated the break-up and why. If he broke up with her over a deal-breaker issue, that’s about as safe as it gets … regardless of her desire to reunite.

    Your boyfriend may be oblivious to his ex-girlfriend’s desire to reunite, or he might be politely ignoring it and hoping it will fade. I don’t know whether you should point out that she’s pursuing him.

    If you decide to point that detail out to him, you’ll probably want to express it as your opinion (you certainly don’t have proof). If he disagrees, ask him whether she calls her other friends as often as she calls him, whether she visits her other friends as much as she visits him, and whether she cooks for her other friends as much as she cooks for him. Let him draw his own conclusions.

    If your boyfriend is trustworthy (and you know him better than any of us), then you don’t need to worry.

  3. 23

    You know… I’ve been skimming through these comments and maybe I’ve missed it… but I guess the one question that hasn’t been asked is…

    “Why is it important for you to still be around this person?”

    Instead of being jealous or untrusting… ask that question and listen to the answer…

    That should give you all the info you need.

    Oh… and “Just because” doesn’t count… 🙂

  4. 24
    Avis Bailee

    I think, YOU were the one who had the strong reaction to your boyfriend’s behavior – not him, not his brother who’s known your boyfriend all his life. His conduct offended your sense of propriety. And when you’re coming from a place where it’s your manners rulebook being violated – no matter how universally offensive his behavior may be or how irritated it makes you – it’s hard not to appear as though you’re imposing your own code on the other guy.

  5. 25
    Patty Pasadena

    That is a tough one.  It sounds like he is really not over her.  I just watched a movie called feast of love with greg kinear and he married a woman who was not over an ex affair and it did wind up breaking up the marriage since when he become available she left kinear for him.  Men always like to obsess about younger women too.  It's annoying.  I would be worried.  XOXO from Patty Pasadena.

  6. 26

    As a “been there” person, I think I talk from experience from both sides of the coin. I also had a boyfriend who had another woman who was “just a friend”and helped him in his business, but who chased after him.   I eventually broke off our relationship of four and a half years because of her and   he went on to marry her 6 months later.
    I am now involved with a man who I also had a few issues with over a very similar situation, another woman chasing after him, knowing that he was with me.   As it had happened before, I was particularly sensitive to it all and we broke up, although he didn’t want to, just said he wanted some space, but I called it quits. It took him two months of testing the waters with this other woman and obviously decided that I was the better bet. We are back together and going strong. It took time for him to earn my trust again, but since then I have also worked on my own feelings of mistrust. I have noticed that he prefers to spend time with me even if one of his old girl mates invites him out (a girl whom he introduced me to incidently). He also will make a point of coming to my place after having been out for a drink with his guy friends. He says he wants me to be sure that he is not with some other woman.
    Lorrie, by giving you both stories, I hope I have shown you that not all men are the same. As Karl said, he may not even know that this other woman is after him. He may also just be stubborn and not wanting to be told what to do. I would approach him and say that it is hurting you that he is allowing this other woman to visit, especially as she lives closer to him than you do. Maybe suggest that if he introduces you to her then you may also find that she is no threat to you. Not many men feel comfortable with his current girlfriend and ex girlfriend meeting and getting to know each other, especially if the ex is still a significant other. If she is just a friend as he maintains then he won’t mind as much. At the same time try not to overreact. Remember a man wants the woman he loves to trust him, and he also needs to be able to solve his issues on his own without added stress. The bonus here is that when he comes back to you wholeheartedly, then he’s done it with his own free will. I hope it all works out for you. Take heart girl. You are not alone.

  7. 27

    Funny stuff – the question is “Can I trust the guy who I know for a fact is a liar?”   That really should have been the heading.  

  8. 28

    I love how you blame the woman for being THE home wrecker of the affair. Yeah she was in the wrong to mess around with him, but why does he get a free pass with (with his consent) in parentheses? He made the decision to cheat. He is JUST AS responsible for the demise of his marriage as the woman you dub home wrecker.
    Yeah, he wants to see her again because he still has feelings for her. If it was not a big deal then he wouldn’t see her at all.
    He wrecked his OWN home. Relationships, entanglements and affairs take TWO! It’s never just one that is the wrecker.
    I hate when people put the scarlet letter only on the woman when the man has free will too. He was able to decline her invitations then just as he is able to now.

  9. 29

    You should not be jealous, you should be GONE!
    You’re not his girlfriend.   In his “little man” mind you’re “another” mistress
    You don’t deserve this and neither does he.

  10. 30

    Many years ago, when I was married, and going through very tough times in my marriage, my (also married) boss wanted to get involved. I confess that I was young and inexperienced, and bought into some of what he said about certain things being “the American way” that, according to him, I had to accept and go along with, unless I wanted to stand out as a foreigner. So even though we never had an affair per se, he got farther than he should’ve. But eventually I pushed back and he then got involved with another woman, also married, who also worked for him. She then ended things with him because she’d started an affair with another married coworker. I realize this sounds like a soap opera, but this really happened and I had front row seats to the whole show. What I learned from this experience is that, it takes a certain kind of character and a certain mindset to get involved in something of this nature. Not only do you have to lie to everyone you know, and remember all your past lies so you can keep your stories straight, but first of all you need to lie to yourself. You have to be able to convince yourself that what you’re doing is good and you’re not hurting or using anyone. Like I said, it takes a certain kind of person to be able to do all these things. The kind of person that I would never get involved with, because, let’s not sugarcoat it, he is a habitually lying scumbag that can’t be trusted. This is all a long way of saying that I would not have gotten together with OP’s boyfriend to begin with, if I’d known his history from the beginning. And if I’d found it out later, I would only stay with him if I saw solid proof that he’s completely turned his life around. Him being friends, and making lunch plans, with his former mistress, is proof of the opposite. My advice is the same as previous commenter’s, get out.

  11. 31

    go ahead and tell him that when he goes out   on a date with that ‘friend’ woman you will go out for lunch with one of your ‘exes’ -friends. Reassure him that you are ‘just friends’ and that ‘nothing is going on’. Let him FEEL the taste of his own medicine.

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