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”?    



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. 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.

  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.

  21. 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

  22. 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.

  23. 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… 🙂

  24. 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.

  25. 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.

  26. 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.

  27. 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. 

  28. 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.

  29. 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.

  30. 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.

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