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.


Join our conversation (32 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    My ex-husband had a “friend” who was enagaged and assured me that she was not sleeping with him while I was pregnant. Well, they are now married and I am left taking care of my son alone. Don’t trust the woman and let your man know that it is either her or you. You just need to be brave and leave if he chooses her.

  2. 2

    I’m sorry, but why is it all the other woman’s fault. Maybe the letter has been edited, but I don’t see any blame directed at the man. “She” invited him to her hotel room, “she” initiated contact later on. What’s his role? Obviously, he must be getting something out of this, because as well all know, men don’t just do this out of charity. How many men simply break off e-mail contact, or never call back again when they decide they’ve lost interest? Is it so hard for him to have friends that he needs to keep up a friendship with her? What are they talking about? Hobbies? Shared interests? I think he keeps this going because he derives some sort of satisfaction from it.

    Evan is right on. They key here is that it makes you uncomfortable. If he respects and loves you he would care about your feelings. Of course he will tell you its nothing to worry about. What is more important to him – making sure he doesn’t cause you grief, or keeping up this friendship? This isn’t just about wanting to have a night out with the boys. This relationship was something that meant a lot to him.

    A friend of mine was in the exact same situation for four years. Same same – “just friends” and so on. Four years later they finally break up, and he goes on to a relationship with the “ex”.

  3. 3

    How many times have they gotten together since she moved an hour away? If it’s once, I’d let it slide, but if he wants to make it a regular thing, then he’s got an ulterior motive.

    I agree with Evan, Ashleigh, and Li-Ann. How would your current bf react if you started hanging out with YOUR ex (and I’m assuming you’ve had at least one)? Lay down the law and see how he reacts, otherwise you get to start “dating” other guys.

  4. 4

    Well, you’ve already had an argument about his maintaining a “casual, intermittent friendship” with this woman. Since then do you think ANYTHING you say will convince him to back off? Maybe an ultimatum would persuade him to choose you, or it might just make him hide this casual, intermittant friendship from you the way he hid the affair from his wife.

    I can understand you not being comfortable with this at all, but it would seem to come down to you either staying with the hope nothing developes, or walking now before anything does.

  5. 5

    If they are going to keep in contact I would recommend that both couples meet. The woman who wrote this letter, her boyfriend, the other woman and her husband. All these secret meetings and sneaking around are just inviting trouble. What the heck do you think they are going to talk about, just the 2 of them? Reminiscing about old times, perhaps??? Geez, this woman had enough influence on him that he ended his marriage over her. I mean I have ex’s that I’ve managed to maintain casual friendships with after we broke up, but she’s more than just an average ex. Dude was in RECOVERY over this chick. I believe the word devastated was used… damn. Even if now (and that’s a big if) the reasons they are meeting are initially innocent, there is too much history between the two and it’s inviting trouble. Both the woman writing this letter and her boyfriend are asking for a world of heartache if things continue this way.

    1. 5.1

      I think you’ve made a good point. He didn’t end the affair and he was devastated. From what it sounds like, he left the marriage after his mistress dumped him.

      Perhaps he’s still in love with his ex-mistress, never stopped loving her. Has maintained contact in hopes of winning her back some day. Not unheard of. If the affair truly is over and he is ready to move on and find love with someone else, he should be willing to let go of his ex.

      Holding on to the past keeps you from moving on and having a future. If he isn’t willing to cut off all contact with the ex-mistress for the woman he claims to love, he doesn’t love her.

      An hour drive isn’t very far. I’ve commuted 2 hours twice a day for years. Their contact will increase. With their background of intimacy, an emotional affair is guaranteed to develop quickly. And unless one of them has great self-control, the sexual affair is bound to follow. Now there are also her husband and child who stand to be hurt by an affair.

      If he’s thinking clearly, he’ll see cutting ties is for the best. If he’s lying to himself, he’ll be just like the alcoholic who thinks he can “have just one or two drinks and stop”. He’ll just see her occasionally for lunch, or drinks, or coffee… but that’s all.

  6. 6

    Evan said about your boyfriend giving her the boot, “….if he cares about you, he should”.

    That says it all. We’re not talking about one of his old platonic college buddies – it’s a former lover. He slept with her. You have every right to feel weird; he should respect your feelings on this one.

    I also don’t think he’s so innocent here – he cheated on his wife and feel for someone who did the same. So what makes you think he won’t do this again?

  7. 7

    A “casual, intermittent friendship? I’m a guy and I have to laugh at that one, talk about justification.

    I’m with Evan to the point that there should be a concern. It’s not necessarily about infidelity but about agreements, particularly his to agree not to see her. He shouldn’t have agreed if his casual, intermittent friendship was so important to him. Frankly it just reinforces the fact that he is easily led in directions which aren’t necessarily conducive to a healthy relationship.

    That said I suggest compromising. Sure, he should get together with his casual, intermittent friend along with his current love interest; why shouldn’t they get together? And since they only live an hour away they should be cordial and invite the new husband along. They can chat about old times.

  8. 8


    You definitely have a right to be concerned about this “friendship”. Look at what this friendship cost him. He ended his own marriage because of his feelings for this younger woman. I find it odd that she would want to continue any type of relationship with him especially since she is married now. I would call her a homewrecker at this point. Is she interested in him because she knows that he is in a relationship with you? It seems as though she likes to divide and conquer. Don’t you dare let her! You must put your foot down on this situation. I don’t like the idea of giving anyone an ultimatum, but in this case you have to. If he really cares for you and I think he does, he will end this friendship once and for all! God Bless!

  9. 9


    I would advise spending some time on the website, specifically in the “just found out” and “general” forums. Even the faq section would be eye openning. After this, determine if it is reasonable for your boyfriend to see his old mistress or, indeed, if you even want him to be your boyfriend after this. The sad fact of the matter is that he probably still harbors some feelings for her. I sometimes have to remind myself regardless of Evan’s statements that we are not in the 1950s anymore but, no matter how much it seems like infidelity is the flavor of the month, and I can not say this more clearly, IT RUINS LIVES. It is like a cancer with infectious tenticles that spread out and effect people who you would think never would be. My ex cheated on me about 3 years ago or so and I barely survived. The guy who was involved, also married, has no idea how lucky he is to be alive, and I’m not exaggerating. Friedships have ended and everyone is worse off financially. Ask yourself if you want to risk this.

  10. 10

    Drop him like a hot potatoe! All the red lights are on flashing right in front of your eyes and you’re battling to close them: SHe came back to continue a hidden contact (since you say her husband is unaware) and your BF still cares more about her over your relationship with him, since you’ve made it clear you’re against the “friendship”. Your BF is completely unreliable. Infidelity and heartbreak will occur, as he even struggles to maintain contact with the homewrecker (if that’s the kind of woman he likes, as we all know by now, you are not going to change him). Wise up, girl!

  11. 11

    Granted, she knows her boyfriend and she doesn’t know this woman.

    However, if the “once a cheater, always a cheater” rule applies to the woman, then it also applies to the man. After all, who did she cheat with?
    Who was married, decided to cheat, and cheat with an engaged woman?

    People can and do reform. I am only mentioning this because there has been some text in this thread with all of the suspicion on the woman with the implication that the man is just some helpless victim taken under a spell.

  12. 12

    Reading one of the earlier comments, something came to me. I was wondering why his ex would initiate contact again. After all, she chose another man over him, and left him devastated. I think that she might now find him a bit more desirable because he has a new girlfriend. Now he isn’t just a “devastated” guy, he’s a challenge.

  13. 13

    THANK YOU ALL!!!!!!

  14. 14

    You may also want to consult an actual trained therapist. You wouldn’t go to a florist to ask about your car.

  15. 15

    If you aren’t jealous you are a naive idiot. I would bet my next paycheck your boyfriend is still “tapping it.” When he is away from you, he is probably with her. The two of them probably have animalistic sex which includes him drooling and sweating all over her wanton body. He still is talking to her because the sex is the best he’s ever had. Take it from me. Been there, done that!

  16. 16
    Michael Ejercito

    Evan is absolutely right.

    A fourteen-year-old with no relationship experience would come to the same conclusion.

  17. 17

    You have a right to be jealous! Hes cheated on a marriage with this woman. If hes as crazy about you as he says he is than their “no big deal” friendship, is seriosuly a no big deal. He can get rid of their “friendship”. Im not saying you have to get rid of him. My boyfriend and this girl “Leanne” were constantly hooking up through their teenage years, but only when she was hitting a rough spot or planning on breaking up with them. My boyfriend fell head over heels for her (b4 we were togethr)…he confessed his feelings to her finally but a lil too late, she had a 1 year old and was pretty much married. Not even 6 months later, she broke up with her boyfriend or fiancee or w/e…and just like all the times b4, you got it…she was calling my boyfriend to hang out!! Naturally i lost it…but in the end he was crazy about me, he completely ended all communications with her, even told her that b/c of their history it wouldnt help our relationship, so having a friendship with her wasnt riskl losing me…so moral of the story is…ppl arent blowing shit outta their ass when they say hell give her up for you..if shes really part of his past n he really is crazy about you, hell do it.

  18. 18

    Update on my situation: A couple of weeks ago I busted him e-mailing the former mistress to say “hi, keep in touch” and then he tried to lie about it. He accused me of having “trust issues” and if I would just trust him, I would see that an occasional e-mail or lunch is no big deal. He assured me that she was no threat to our relationship but was unwilling to give up contact with her and said if I couldn’t trust him then maybe we shouldn’t be together.

    So I dumped him.

    Sigh…back to the dating world I go.

  19. 19

    Anyone’s advice would be greatly appreciated:

    My ex boyfriend (Cory) and I have liked each other since i was 15 and he was 13. We dated off and on until i was 16. When i was 17, and he was 15, we were very steady. We dated for two years. We are perfect for each others families and for each other. Our familes have noticed this.

    I am now 19 and he is 18. We broke up September 2007. I took it very hard, he just wanted space “to find himself”. He suggested we see other people. AFter a month, I chose to date a guy that i had an “old flame” with back when i was 15..there had always been something there. We’ll call him “Jay”. Jay and i have been dating since October 2007. I only wanted to date Jay to help me get over Cory. I still talked to Cory a lot during the first 4 months of me and Jay’s relationship. This killed both of them. Cory wanted to get back together and never thought i would date anyone else. I am torn as of what to do.

    It is now June 2008 and i am supposed to be going to Florida with Jay’s family in 2 weeks. However, i cannot stop thinking about Cory. I never stopped thinking about him. I know he is what i want, but i have got myself too involved with Jay.

    To make matters worse, Cory and Jay run into each other alot. They graduated one year apart from each other and we are all from a small town.

    How can i have fun on this vacation when my heart is with Cory. Jay and i have a good time but i do not seem a prominent future like i do with Cory.

    How do i approach this situation?!?!

    Any response is greatly appreciated.

  20. 20

    It appears you are stringing Jay along since you claim your heart is with Cory. Do him a favor and let him go to find a girl who really does love him.

    You are only 19–you really might be better off giving yourself (and Cory) some time to be single and date others without getting serious.

Leave a Reply

Your email address will not be published. Required fields are marked *