“My Fiancé Has Been Sending Inappropriate Messages to His Ex During Our Whole Relationship”

text message

My boyfriend of 2.5 years just proposed to me. It was great, and I was on cloud nine. Our relationship didn’t have the smoothest start. He was very back and forth in the beginning, but we are truly best friends, with more love for each other than I could ever explain. So naturally, when he popped the question, I was thrilled…until I found out he has been emailing with his ex-fiance throughout almost our entire relationship.

He was previously engaged over 6 years ago, to a girl he dated off and on for 5+ years. They were broken up the first time for almost two years when they ran into each other and decided to give it another shot. Shortly after, they were engaged. It ended up running its course again, for reasons that I don’t entirely know. I knew he had contact with her when we first started dating, but, when we became serious and I explained that it bothered me, he said he would stop (no Facebook, Instagram, etc.).

Cut to this week. In one of my less proud moments, I looked at his phone out of curiosity regarding engagement congratulations. He has several girls from his past who I’ve expected may have been more than friends at some point, who he still maintains contact with. I was interested to see what their take was on our engagement. Not cool, but the truth. I was also interested to see if his ex knew we got engaged and, if so, did she reach out to him.

While looking, I uncovered over a year’s worth of emails between the two of them. The first few I saw were a few months into our relationship. He sent her an “e-card” with some joke about having sex. They proceeded to talk about how they’d like to do “that” again. It went back and forth, but I was seeing more red than actual words on the screen.

Another email started because she deleted her Facebook account after seeing a photo of my fiancé and me at a concert together. He proceeded to tell her that he only took the picture because the “lights were cool” and that he would have preferred her to have been there instead of me. Then a month or so later he sent an email after her father passed. I completely understand his concern and need to express condolences, but he went into great detail about how important her family was to him. He then signed it with “Love,…”.

Then there were more emails between the two of them about six months later, which was well into our relationship. In those, they talked at great length about their relationship, how no one makes them feel the same, no one understands her like he does, how hard it is for him to see photos of her and her husband, how much she misses him. And finally, she complained thoroughly about her marriage and said she wished she could be with him again, but she said she knows she can’t “ask him to wait” for her. He said he was confused, flattered, and missed her too. I had had enough and stopped reading. I confronted him about it and a blow-out fight ensued.

The next day he deleted everything. Later on I saw an email from her telling him to delete everything and figure it out. He says he’s devastated and swears that all of the emails were over a year ago. But when I pressed him for honesty, he said he thinks their last emails to each other were “like 8 months ago.” I don’t know if I believe that. I don’t know what to believe.

He says he’s never loved anyone more than me and wouldn’t have proposed if he weren’t certain. I’m furious, heartbroken, humiliated. I simply don’t know what to do. I don’t feel like I can trust him again. They were broken up for two years before and got back together. How can I be sure that, if our marriage gets rocky someday, or if she divorces her husband, they won’t start talking again? He says he reciprocated the conversation because of the “attention.” To me, that sounds like the making of a cheater. We hit a speed bump, or don’t, and someone else gives him some attention, and then bam! Please help me figure out where to go from here. — Blindsided in Boston

I can imagine the fury and hurt and betrayal you’re feeling now — and at a time when you should be feeling joy and excitement. It may be hard to see it this way, but there is a silver lining here, and that’s that you have made this discovery about your fiancé and his relationship with his ex before tying the knot. Can you imagine how much worse you would feel and how much more complicated things would be if you were married and just discovering that he was expressing feelings for someone else months earlier and well into your relationship? That’s not to say that you should forget about marrying him and that your relationship is over; but this new insight does provide a much-needed opportunity to evaluate your feelings — especially your trust level — and to communicate and to think very carefully and thoroughly about what it would mean to commit to this man for life.

If I were you, I would put the engagement on hold until you know for sure you are ready to marry your boyfriend. You obviously have some doubts — doubts I believe existed even before you had proof of your boyfriend’s transgressions. Why else were you so curious what his exes thought about your engagement? Why else would you violate his privacy and snoop through his phone, with the sole purpose of seeking messages from ex-girlfriends? Something inside of you felt unsettled about his past relationships. Your gut was telling you something was “off.” And your gut was right.

So, what do you do now? You take some time to think about things and talk about things and think about things some more. You ask your boyfriend for full transparency. Tell him that trust has been broken and, in an effort to re-build it and save your relationship, you want access to texts and emails. Maybe that means his sharing of his passwords with you, or maybe it means his handing you his phone or logging into his email and Facebook accounts, whenever you might ask, and letting you scan through his messages. You also need clarity about when his feelings for you — and when his feelings for his ex — changed. If, at some point into your relationship, he was telling his ex he didn’t love anyone like he loved her and that he’d rather she be with her than you, when did that change? How did it change? What are his feelings for his ex now? And how would he feel if he never, ever spoke to her again (a fair request from you at this point, I think)? You also need to have clarity about the nature of his breakup(s) with his ex and have any questions you have about her or any of his other exes answered so that you don’t feel the need to search through messages and social media pages to find the clarity you seek.

I would set a timeline for when you would need to feel positive enough about your relationship to move forward (with an engagement and making wedding plans). Decide how long you’re comfortable waiting and how long you think it might take to earn back your trust. Maybe six months? Maybe less, maybe more. You have to decide for yourself (and it’s ok if it changes, but having an idea in your head for when you are going to MOA, whether it’s with him or without him, will help you get through this period of figuring things out). And if, when that time is up, you don’t 100% trust your boyfriend and his intentions and feel 100% that there are no other women competing for his affections, you shouldn’t marry him.

Another silver lining that may be hard to see now but does exist: you will have a better relationship in the future, whether it’s with your boyfriend… or with someone else. If you decide to stay with your boyfriend, it will be because you have worked through your current challenges and your bond will be much stronger for it. And if you break up, it will be because you know in your heart that you deserve better, and you will be far less likely to settle for anyone who doesn’t fill you with certainty about his commitment to you.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. I don’t know, if my fiancé had been emailing his ex about how much he missed her and would rather be with her throughout much of our relationship, I don’t think that’s something I could live with. A weak moment, a rough patch, those are things that can be fixed, but ongoing inappropriate messages with your ex throughout basically the entirety of your relationship? Definitely put the engagement stuff on hold, like Wendy said.

    1. Agree, I don’t think I could get past that. Specifically, I don’t think I’d WANT to work through stuff with a guy who had committed such a major betrayal of my trust. I don’t think I’d be able to think of him as a partner. But Wendy’s advice makes sense in that if the LW completely breaks it off now, she might have regrets and wonder what could have happened.

    2. Yep, me too. That would be the end. Adios, hombre.

    3. Woo, the Kates agree with me! Lol.
      Oh, and I totally agree that the advice is probably good for someone who doesn’t want to break things off immediately, but dude, she only read through the first year’s worth of emails, I can only imagine what’s in the second year that warranted deletion…

    4. Absolutely agree. He’s been doing this literally the entire time you’ve been together. That means he’s never really been committed to you.

      There’s no way I would ever trust this guy again.

  2. If it were me, the engagement would be on hold as of right this minute.

    I would also be letting him know that we would be taking some time apart, and that he needed to figure out what (and who) he really wants. It sounds to me like he can’t decide between the LW and the ex, and he’s been clumsily trying to keep them both in his life.

    So, I’d be taking the pressure off. The wedding is off, indefinitely. The relationship is on hold, maybe temporarily, maybe permanently, depending on what he decides. I would also want him to have a long talk, or talks, with his ex, to help him figure out what he wants. He clearly has unfinished business with her.

    I wouldn’t want him back until and unless he was 100% sure that he wanted to be with me, and only me. If he can’t be sure, we don’t get back together, and we sure don’t get married.

    I’m so sorry, LW. 🙁

    1. I would definitely hold off on the engagement too, but I wouldn’t give him time away, and time to think about who he wants to be with. After two years if he can’t figure out right now who he wants to be with then I think it’s pretty clear that he isn’t going to be 100% into this no matter what he says. This just sounds more like something in the movies, where they take time off, and he magically comes to the conclusion that he really does love her, and wants to be with her the rest of his life, and shows up at her work, and has to convince her best friend to get her to talk to him again, and once he gets past that, they live happily ever after.

      1. I agree. If you say, “Who do you want to be with?” and his response is not immediately the LW, then I would not want to wait around for him to “figure it out.” If he doesn’t know after 2.5 years and an engagement, what will a few more months do?

      2. Word.

  3. To be honest I would probably end things. Two reason: 1) He was unsure enough of your relationship to tell another person he would rather be with her, just a year or so ago. I would have trouble believing that he’s really committed now. 2) Instead of being honest and open, he deleted the emails and apparently continued lying regarding the timeline (how long ago they stopped talking). So you have no way of knowing if he’s telling you the truth now.

    1. Avatar photo muchachaenlaventana says:

      yes! He is a liar—how can a person live one life but be telling someone else all of these things about the life they would rather be living? How could anyone want to be with someone capable of such deceit and in-authenticity. It is just sickening. I guarantee LW if you keep pushing that 8 months that they last emailed will keep being pushed up—that is the way people who lie function—they lie until they are called on it, and keep doing so until they really can’t anymore.

    2. Yeah, the fact that he deleted those emails really jumped out to me. And apparently he was still in contact with the ex? Especially once he was busted? Not the sign of someone who wants to be open and honest and regain trust.

  4. If she saw an email from the ex telling him to “delete everything and figure it out” it doesn’t sound like the last contact was 8 months ago. Sounds like they’re still in touch (obviously he told the ex the LW discovered their emails)

  5. Ooookay, the email from her the day after the fight telling him to “delete everything and figure it out” would be enough to make me MOA immediately.

    1. Especially because it’s pretty clear that the ex knew about the fight. How did she know? Because he told her about it.

      1. Exactly! And it doesn’t sound like he said he wanted to stop talking and figure things out. Which, call me crazy, I would want *my* fiancé to say if he’d gotten busted talking to his ex.

    2. Avatar photo Raccoon eyes says:

      The whole deleting the emails immediately is what struck me the most. What was the point of it? Evidence lying around is never a good thing, but if that was his first reaction, it smacks of there being A LOT OF STUFF that LW would find awful, and probably downright appalling and deplorable. And it seems like maybe he thought “out of sight, out of mind,” so by getting rid of them….the problem would also disappear. I guess what Im saying is that is just so grossly disingenuous.
      Im so sorry you are in this mess, LW. I concur with everyone else that you need to think long and hard about trust and if you will ever be able to be satisfied with transparency or whatever you all decide on. I mean, there is always a way around it- the simple creation of another email is all it takes.

  6. Yeah, I think this is a huge transgression and one that will be tremendously difficult to get past. This is months and months of betrayal – and not just casual conversation. He outright says he would rather be with her than you! That’s an emotional affair at best. Do you have any reason to believe he didn’t actually see her?!
    In addition, let’s talk about the snooping. Sure, your gut was right in this case, and you found out some very important information. But will that ever stop? I had an ex where I would look at his phone whenever I could because, duh, I didn’t trust him. And every single time I did, I felt fucking awful – about myself, about our relationship, and about him. Maybe you’ll be able to trust him again after having that be the norm for awhile. But, won’t he be on his best behavior during that time? And will you ever feel comfortable enough to give him his privacy back? If the answer is no, do you really want to be in a relationship where you are basically monitoring his every move? That does NOT sound like a good time.

    1. I’m glad you brought this up. I’ve been thinking about this. Every time we get a letter from someone saying they snooped, we always say they invaded the other person’s privacy, there are bigger issues, etc., which is all true. But, if your gut is telling you something, well, where’s there’s smoke there’s fire, right? I know that when I am feeling totally secure in my relationships, I don’t feel the need to snoop. And how many people would be honest and forthcoming when asked directly, “Hey, are you cheating on me?” I, personally, would rather have some kind of proof in hand before I make such an accusation. Someone who has no problem cheating also has no problem lying. So I guess I’m saying that snooping isn’t so bad, although I do agree that it is indicative of serious issues.

      1. Also does it maybe work better if you just tell you partner that if they ever want to “use” your phone to just go ahead and use it? Like I know my wife would never care if I just picked up her phone or computer, and started using them, and it just makes me feel like she has nothing to hide, or she would tell me her passwords so I can use these things. My wife has passwords to the things I have password protected which is just really my work computer, and if she ever wants to pick up my phone and use it that is fine, and if she happens to go through anything that my phone is connected to without me knowing that is fine too, because there is nothing there to worry about.

      2. RedroverRedrover says:

        My husband and I just ask if we want to use the other person’s device. The answer is always yes; the asking is just a formality done out of respect. I’m not the type of person who can tell someone to just go ahead and use my stuff whenever they want, and neither is he, so this works well for us.

        But I would never, ever give him the password for my work computer, nor would he give me his. Our work computers and the data on them are owned by our respective companies, and we’ve signed employee agreements about privacy. Maybe not all companies have that, but we both work for large tech companies and they definitely do.

  7. Sunshine Brite says:

    I would end it. And I say that as the nostalgic sort who tries to be friends with exes. He didn’t keep anything above board, let it roam towards sexual talk (yes that one was awhile ago, but it sounds like you were supposed to be exclusive then). The fighting and deleted emails are a big problem. Sure, take your time to figure things out, but he’s already shown his colors in my opinion. He even wished that it was her and not you at a concert, that’s not okay. I think you should take that time to plan a safe exit away from him.

  8. Bittergaymark says:

    Eh. The ex is STILL married and all of this was MONTHS AND MONTHS ago — what? 8 minimum? Possibly even a year ago? Moreover… Much of it transpired when their relationship was new. And instead of dumping you for her — he asked YOU to marry him.

    Think about it.

    1. That was my gut response. If she looked through all the emails she should know when they ended. She said that he change his tune when she pressured him to know when they ended so she is suspicious. But yeah I was very curious about the timeline for when she asked him to stop communicating with her at all, and when the last emails were exchanged.

    2. Still he sounds like some behavior was at least a little shady for at least a part of their relationship. I guess she needs to decide whether she trusts the last 8 months or year or whatever, or if she thinks it could happen again.

    3. Avatar photo muchachaenlaventana says:

      Eh I don’t agree with this, they have been dating for 2.5 years and the communication stopped 8 months ago…so for over half of their relationship that this has been going on. So he has been lying to her for all of that time and writing things like his ex is the only person he ever loved and who he wants to be with. A lot of shitty people marry/get engaged to people for stupid reasons–a lot of people do so after lying/cheating for significant portion of their relationship. Him wanting to marry her isn’t enough of a reason for her to stay with him—It isn’t like it happened when they had known one another 2 weeks and then stopped. This has been ongoing throughout probably their whole relationship.

    4. Is this sarcasm? This is sarcasm right? He was faithful to her for the last 8 months of their 2 1/2 year relationship…and this is supposed to be validating because he proposed?

      1. Yeah, I took this as sarcasm too…

      2. Avatar photo muchachaenlaventana says:

        ha I missed the sarcasm bit…which if it was ignore that response.

      3. bittergaymark says:

        No. It’s NOT sarcasm. Good lord, everybody expect people to be fucking monogamous out of the fucking gate and HELLO! NEWSFLASH! That rarely fucking ever works. The infrequency of the emails is hilarious. Like months and months passed with NOTHING!

        This is a mountain out of a molehill.

        But it’s probably all mute as I’d dump the ass of anybody who casually violated my privacy. As will — I predict — he.

      4. Who said anything about being monogamous out of the gate? How about being monogamous when you are in a committed relationship?
        If the argument is ‘go by how he has treated you the last eight months and be happy you got a proposal’ ….then you have officially drunk the Kool-Aid. I trust you won’t go on a tear the next LW that writes in saying even though there were plenty red flags I married a guy anyway and now he is doing the same things again. There won’t be any remarks about how desperate women are to get married at all costs – right?

      5. Bittergaymark says:

        Honestly? A handful of emails isn’t even vaguely non-monogomous to me. Period. I swear… All this emotional affair malarky is such bullshit. It’s tedious. And silly and vapid…

        Not to mention NEEDLESS drama which — I guess — it seems most everybody needs as they constantly create it.

      6. Avatar photo muchachaenlaventana says:

        Have you ever been with someone who was carrying on an emotional affair? I can assure you it is not bullshit. In fact, I would be more willing to forgive and forget a meaningless one night stand than a years long emotional affair. Also she didn’t say a few emails, but a years worth of emails which could be any number, but my guess is a few a week.

      7. You wouldn’t be upset if your sister’s husband was emailing some other woman confessing his love to her – 8 months ago? You’d tell your sister she is manufacturing reasons to get upset? A betrayal doesn’t have to be physical to be a betrayal.

    5. Yes, I agree. LW, I do believe that your fiancé was not in a place to really commit when you first met. He had to work out what really happened in this last relationship. It sounds like you guys need to really talk about everything but this wouldn’t be a deal breaker for me.

    6. Or so he says after he conveniently deleted all proof to back up his case. Methinks something is rotten in the state of Denmark.

  9. I think you have to realize that when he is saying ” he’s never loved anyone more than me and wouldn’t have proposed if he weren’t certain” to you it is the same as him saying ” no one makes them feel the same, no one understands her like he does” to her. He clearly is just saying this stuff to keep you both in his life. He probably is in love with both of, but the truth is that he is a liar, and has been lying to you your whole relationship, and you deserve better than that. I would definitely call off the engagement, and probably leave him, because as much as he says he is going to stop, he never will, he will just be way more discrete about it. You have to understand that she isn’t going to stop contacting him, and he wont be able to resist texting or emailing her back.

    1. zombeyonce says:

      I agree that he’s just going to be more discreet about his contact with his ex. I don’t think handing over his passwords to email and social media will help one iota, and here’s why:
      1. He could SO easily just make a new email account LW doesn’t know about and use that for contacting the ex.
      2. LW will never be able to stop checking these accounts and having the access will just make her more paranoid about something going on. This access (even if he really did stop contact the ex) would just continue her lack of trust forever, and even if she was able to stop herself from checking for trusting him, every time they have a fight or he seems in a weird mood, she’s going to wonder again.
      They need counseling if LW wants to give him a chance. Even with that, I think the trust will be incredibly hard to get back and she’ll always wonder.

    2. so, has he really been lying this whole relationship or has he been omitting. So he was working out the emotions of this old relationship but is a set of emails periodically over two years systematically lying?

      1. Avatar photo muchachaenlaventana says:

        he definitely has and he lied about when their last contact was. He has literally been living a lie–telling one woman one thing while building a life with the woman he doesn’t claim to love as much–gross.

      2. Yep – lying by omission. She asked him to stop once they became serious. He said he would and not only did he not stop – he hid it.

      3. He had no business proposing to another woman while he still had feelings for his ex. Lying by omission is still lying.

      4. In re-reading this, I don’t think it was a lie by omission. He was asked to stop, he said he would, and he didn’t. that is a direct lie by deed.

  10. PumpkinSpice says:

    LW, I am so sorry for you. I personally don’t agree with snooping, especially for the reason you explained, but in this case, it looked like your gut feeling paid off. You need time away from him. He is still contacting the ex, obviously, by the last email. That would be like a HELL NO to me and a slap in the face! The fact that you found all the emails, had a big fight, and then he turned around and told his ex about it and the fight tell me two things: 1) He has no respect for you and your relationship, and 2) He will not stop contacting this female. She also is to blame here. She is MARRIED! But throughout her relationship and engagement and marriage she has been having an emotional affair ( & possibly a physical affair, sorry but it is quite possible that they met up on occasion as well) with your boyfriend. Neither of them care, or trully care about what your feelings are in all of this. I would dump his ass and then work on myself, take some of the$$ I was saving for the wedding and go on a vacation by myself to get away and clear my head and think. If you are intent on saving this mess of a relationship, I don’t know what religion you are, but some require marriage counseling before you can get married in their church. This is a route you both might want to look into. Go to couples counseling together where you can say what you both need to say in a neutral place and try to work on yourselves and your relationship. But honestly, do you want to live with the constant worry that if you have an argument, or a disagreement, that he might run to this ex? Are you comfortable knowing she knows all about you, and your relationship? She is too ingrained into your lives. You should just MOA, at the very least, cut off all contact with him and then agree to reevaluate things at a chosen time in a month, or two. But at the very least, take some time away from each other, and definitely put the engagement on hold, this is not a good time to be worried about planning a wedding and a life together. Good luck LW, and best wishes with your decision, what ever that may be. And please update us in the future.

  11. PumpkinSpice says:

    Oh and by the way, this line “we are best friends, and have more love for each other than I can explain” is bullsh*t. He does not love you the way you think he does. If he did, this would not have happened. You need to think long and hard about this betrayal and where you want to go from here.

    1. Very true. She knows from his own e-mails that he loves his ex more than he loves LW. His ex is apparently unwilling to leave her husband. If not for this obstacle, I doubt he would have proposed to LW. And the whole ‘the last contact was a year, no make that 8 months, no obviously I contacted her immediately after our discussion’ is a lie. He has been in continuous contact with his ex. If the ex ever leaves her husband, this guy will be there in a shot.
      For those who say not to worry so much because it was just an emotional affair, I say that the reason it didn’t progress to a full-blown affair was not for lack of trying on his part. LW should MOA immediately for her own self-respect. This guy played her for a total fool. The tone of the message from ex is also rather telling.

  12. This is one of the more fascinating types of conversations we sometimes have on DW. Can trust really be rebuilt after it has been broken? Is trust just one thing, or is it layers of importance and betrayal. For example, I have promised my wife to do some household project or take out the garbage or pick up milk – and I have BROKEN those promises. But they are not really about anything important. They were things you could make up for later. But since the day I told her loved her I’ve never told anyone else that i would want to be with them. I think if she did that to me, i would be broken. I think i would never really trust her again. People have broken my trust for a lot lower stakes. I’ve been able to continue being friends with some of them. But none of them were my romantic partner, and i have never trusted any of them with anything really important ever again. LW, you don’t trust him. Do you think that can really change, without you lying to yourself?

  13. His excuse that it was just for the attention is bothersome. You were at the stage of dating and getting closer (and on your way to become engaged) – this is the exciting part!…and he needed attention then? A year ago is a drop in the bucket. That is no kind of significant passage of time…let alone 8 months. What is going to happen 7 years into a marriage with kids and bills and responsibilities? What can he do to show you he won’t need outside attention then?

    I think there are the type of men that are chronically unfaithful. They want that life and they won’t ever change. And I think there are the type of men that are “opportunistic” cheaters. The “it just happened!” type. The thing with those type of cheaters is that they more often than not put themselves into the situations that naturally evolve into infidelity. They just keep pushing back the boundaries of appropriateness until they are solidly into the cheating territory. I think that is what this is. He created the environment that could naturally evolve into infidelity. There was an emotional intimacy here that shouldn’t have been and instead of shutting it down from jump – he continued it. You need to figure out if there is anything he can do to show you he won’t cross those lines again…2 years, 5 years, 10 years down the road. For me, there would have to be some serious work done on his part (like with a qualified professional) and suggestions COMINGFROM HIM about how to fix this and the limits on his friendships with women he has had a past with. There is no value in him agreeing to rules you want in place. He has to come up with rules that work for you. If they are his rules – he is less likely to resent them later since they aren’t imposed by you but came from him and he has to actually think how to restore the broken trust instead of just saying yes mindlessly to get what he wants. There should be no engagement talk until you feel secure in a future with him. Good luck.

  14. I am very sorry you’re going through this, LW. Like many others above, I find this to be a large scale betrayal and the idea of the life you will lead if you choose to stay with him sounds like more pain than its worth. It sounds like your fiancee is unable to be honest even with himself about his intentions. And if he can’t be honest with himself then being honest with you is going to be impossible. Sure he could work on his issues in therapy or something, but the level of dishonesty he’s engaged in throughout your relationship indicates deep seated issues that won’t be resolved easily, or quickly, if ever.
    In your shoes, I would cut and run. It will hurt like hell, but I think the pain of trying to keep him in your life will be worse. That’s something only you can decide, of course, but do not feel simply because he gave you a ring that you have an obligation to work on this with him. The only person you have any obligation to is yourself. Take care and good luck.
    P.S. What a dick!

  15. findingtheearth says:

    My father is a philanderer. He does stuff like this all the time. He keeps in contact with exes, random females he meets online, etc. His current wife caught him in May cheating. They still got married in August. She says she trusts him, but I don’t think she really grasps how much he cheated in the past and that, more than likely, he won’t change. My mom said he could go a few years with being faithful, but she was never really sure he was faithful. That is something you have to think about. It may not be an ex next time, it may be someone else he meets. He hid all of this for a very long time from you, it is pretty easy to do it again.

  16. I don’t know if I’d personally be able to stick it out in this relationship. As FireStar said above, you were in the exciting portion of your relationship when this was going on, dating, getting ready to get engaged, etc. If someone needs outside “attention” at that point, how is that reassuring when life gets much more mundane, routine, or bogged down with life’s increasing responsibilities?
    From personal experience, I can say I was in the same situation somewhat, though not engaged, and I would be the boyfriend/now-fiance or his ex in this scenario. I had an ex who I was very on and off with and even when we were dating someone new, our conversations/interactions were extremely inappropriate if either of us wanted these other relationships to work out. I finally knew our on-and-off relationships and essentially emotional cheating on our significant others at the time was over when he met someone after a few years of this back and forth and all of a sudden, the messages, phone calls, etc. stopped. Two months into dating his now-wife was the last time I heard from him. So, from personal experience, when someone is committed to a relationship, they are not texting, messaging, etc their ex inappropriate stuff that would upset their fiance. Your fiance may love you and may think he’s ready to be engaged, but if he’s still getting “attention” and clinging to a past idea of love, he’s not anywhere near ready for the serious commitment and work a long-term relationships takes and you deserve that.

  17. Been There says:

    Been there, done that, and 11 years later, STILL going through it. I think we are on inappropriate contact number 5. We’re heading to counseling after this one since I simply cannot do this anymore. If I could go back in time, we would have been done the first time.

    1. Breezy AM says:

      Me too. Wasted ten damned years on one of these assholes.
      Never again.

      My own stupid fault.
      They don’t change. They just fucking don’t.

      For me the big clue yes is the “delete everything!” mails. Meaning yes, he ran and told her. Like how for me the big clue was the second I hijacked my soon to be ex’s FB status and said oh how fun it is when your wife reads your messages… and not 45 damned seconds later his phone rings and it’s that bitch (yes, I blame him, that doesn’t make her any less of a bitch for participating!) I knew, I knew right then.

      Dump him LW. Do not fall for his BS. Don’t.

  18. So it appears that he and his ex can’t be together as a normal couple, because the relationship has “run its course”; instead, they want to feel the excitement of doing it discretely, behind their partners’ backs, because otherwise they feel bored.
    I found Wendy’s response to be very wise and balanced, but also very forgiving (in not bad way or anything…) If I were in this situation, I most likely wouldn’t even bother to confront him – next time he comes back, my stuff will be gone. Let him figure it out. 😉
    Whatever you fiance said or not, it smells affair to me. I think, taking into consideration the essence of the emails they’ve been exchanging (sex related e-cards? wanting to do “that” again?), there is an incredibly small chance (almost close to none) that things were kept just in the cyber space. It seems that he wants to have a cozy secure relationship, and a more “naughty” and “exciting” one on the side – because things with his ex didn’t work out otherwise.
    LW, once a cheater always a cheater and you know what? Same applies to liars. Trust me on this. I don’t see how you can regain your trust in him after 6 months, or 12, or 24. Be honest with yourself, do you genuinely see a time in the near future (max 2 years) when you will not raise your head and wide open your eyes whenever he gets an email? Or a text? And allow your mind to be automatically filled with all sort of disturbing thoughts? Is it her again? Or is it another woman? And if you do decide to ask him to see his emails/texts/facebook/instragram every day in the next however many years, is this the type of marriage you want to have?
    I am confused about some things and so should you. The main thing being: if he loves you so much like he had never loved anyone else – why was he telling his ex the same thing at the same time you were going out? Where does the truth lie ? Does it even matter ?!
    There’s a saying I love quite a lot: “Fool me once, shame on you. Fool me twice, shame on me”. This is not to say that people don’t deserve second chances, but do you think all the betrayal, humiliation, anger, hurt, lies really deserve a second chance?
    It’s one thing “I got a bit drunk last night with the boys and started flirting with the bartender” (once) and “I’ve been telling my ex how much I love her and miss her throughout our whole relationship, sorry”.
    The more I re-read your letter the more I simply don’t understand why on Earth you would even consider marrying this person. Why would he feel the need to explain himself to his EX why he has posted a photo of you (his current fiance) and him together? And why would she overreact so much about that photo so as to delete her fb account? Is she living in some delusion that you two aren’t together and that he belongs to her?
    And after you found out about the whole thing, why did he come back to HER for… what …. advice? A moan? I think the fact that he felt the need to share the fact that you discovered their little game with her means their “cyber” relationship (or not?) is a lot deeper than you think it might be.
    Please don’t cause this to yourself. You deserve better. You do. You have no kids, I assume no shared property, hopefully even no pets! You have the time to heal from this and get yourself a man who deserves you!

  19. Dump this guy. The big problem IMO isn’t so much that he was flirting with an ex, since it sounds like that was just bored chatter between them. It’s that he denigrated your relationship with him. That’s the kind of thing that will stick with you – him telling another woman he’d rather be with her than you. Don’t go into a marriage where you aren’t certain you’re standing on solid ground. Marriage is way too fucking difficult along the way even with rock solid beginnings.

  20. Although I also disagree w/ snooping, I feel that if you have strong uncertainties/gut feeling that are initiating the snooping, so be it- even though there will be consequences, your relationship clearly has some underlying issues that are prompting these actions.
    I don’t know if I would feel ok continuing an engagement if I found multiple e-mails from my fiance telling his ex he wishes he could be w/ her, etc… Maybe these e-mails were from a while back & things have “changed”… Who knows? That’s up to you to decide, just as Wendy suggested. I agree w/ putting the engagement on hold & setting ground rules/timeline to win trust back…I think this way, you’ll be able to fully gauge how invested he truly is in your relationship.
    No relationship is perfect & there are many ups & downs…It is up to you to decide whether you truly feel in your heart this is something worth working on… Don’t stay w/ him because you think it’s too late, you already have a ring…It’s not too late… If he is not reassuring you that you are his priority & you don’t feel comfortable 100%, don’t marry him. It’s not worth it, you deserve to be someone’s #1 & if he’s not the one- that’s bc the one that IS going to make you feel the way you deserve is on his way to you. Right now, you gotta put yourself first. Good luck to you!

  21. From what you have said here, I think you should probably MOA. He deleted all of the emails and TOLD HER that he’d been found out! The initial evidence was pretty incriminating, but telling her about your fight is downright damning. And if it were me, I wouldn’t want to be in a marriage where I was always nervous about emails. Life gets a lot more crazy when you add in children, a mortgage, illness, aging…don’t sign up for a lifetime of monogamy with someone who needs his ego stroked by another (married!!) woman at 2.5 years in.

    If you decide you want to work on things, he has to be 100% on board for as long as it takes for you to feel he’s trustworthy again. That starts with him realizing what a huge breach of trust he’s committed to begin with. Maybe he’ll be on his best behavior for a month, and then start telling you that you’re being unreasonable, jealous, controlling, etc. That should be a non-starter for you. If he wants you to be his wife, he will do whatever it takes for as long as it takes to prove he’s worthy. If he gaslights you…run.

  22. Avatar photo Astronomer says:

    Nope. Just nope. Get out now.

    All this “go to counseling,” “rebuild trust,” “get transparency and passwords,” and “make a timeline in your head” advice is nice and forgiving and, but really? You can be in a relationship with someone where you don’t have to do all these awful things and forget all these awful things. You shouldn’t have to try to get over a whole relationship’s worth of lies and possibly cheating, because there are tons of people out there who won’t do this at all. Move on and aim higher.

  23. LW, I’m so sorry this happened to you. I agree with everyone else that this is very shady behavior and it seems like your fiance has been carrying on an emotional affair and lied about having no contact with his ex for the last eight months. If he has spent 2/3 of your relationship (or maybe more) sneaking around behind your back and maintaining a relationship with his ex, I’m not sure what is left here to salvage. Is it possible for you to trust him again after he has lied to you for so long? Will you ever be able to get past the things he told his ex? I have a hard time thinking that the true answer is “yes,” and if you think you will be able to forgive him and get past it, you should think about whether you would say the same thing if you weren’t engaged to him and 2.5 years into the relationship. Please do not think that it’s too late to end things or that you have to stick it out because you’ve already invested so much time in the relationship. Eff that. Also, get yourself to a therapist now.

  24. No I would definitely end it.
    1. He said to her that the picture of your date was just because he liked the scenery and he wished that she was in your place?!?!?! I can’t get over that.
    2. figure what out? What’s she talking about? There must be
    Lots that you don’t know….., sounds like he wants to be with her but she would need him to wait?!
    3. His duplicity – you thought everything was great, so it had nothing to do with you being an awful girlfriend and ignoring him or annoying him. Despite his great relationship with you he went behind your back numerous times with emails. Think he’s never talked to her on the phone when had the chance? He sounds pretty narcissistic and I don’t think he’s curable. It would be one thing if he did this after you did something horrible to him, or after years without intimacy (physical or emotional)
    But to do it right away signals he has more severe mental or emotional issues which you should want no part of.
    I know it sucks to be Suddenly unexpectedly single and have to do all that work finding dates etc, but it will be worth it, to have the chance to find a real partner without a huge cloud over your love
    How can you want to marry someone who was so dishonest with you for so long? I’m very glad you didn’t have any kids with him and I strongly advise you to cut your losses now and start the rest of your life. There’s no way he’s worth your time. Even this lady disappeared or died tomorrow I still would not trust this man!

  25. I’d be done with the relationship. Yeah, he says it’s been 8 months since he last spoke to his ex, but with his deleted messages you really have no proof except to take his word for it. Now, if he:
    1. Really had a change of heart
    2. Stopped e-mailing the ex because he was so head over heels for you, his current gf
    3. Even perhaps told the ex to not contact him again
    Then… why would he have deleted them after you had already read through them? It sounds to me, from your letter, that you didn’t read through them entirely or thoroughly, and that you had confronted him when you had ‘read enough’ (as opposed to all). So, if his one argument is that it was so long ago and his feelings changed and they haven’t communicated in fooooooorever (8 months)… Why the hell would he delete his one proof and chance to convince you? That leads me to think that he has communicated with her much more recently than 8 months ago. Or, that his last messages were just as (or even more) incriminating. I mean, this is messed up. And then throw in the fact that surprise, this gal is married and it becomes Really, Really Messed Up. The only thing apparent in this whole situation is that they both have no respect for wedding vows.
    My advice for you is to move on. Run fast, and run far. He really hasn’t done anything to keep or earn your trust, but has shown himself to be untrustworthy.

  26. Hi, I know this was a post from a few years ago, but I am curious what happened…what did you do?

    I am in the same boat. I met the man of my dreams, he treats me better than I have ever been treated( and I have already been married once before…so I know what I don’t want) We had a beautiful engagement! He is a huge golfer…and he proposed on the greens of a golf course…I caddy for him. That was July 2017. In January of 2018- I was contacted by an ex of his who wanted to share some texts with me that were from my fiance. They were def. inappropriate with sexual references. I confronted him and he was very apologetic- was afraid he was going to lose me- and said”He would change all of that and his behavior because I mean the world to him and he wants to be with me. He went on to say- he was glad that this happened before we were married- because it def. made all of the acceptable boundaries very clear to him. He said – we were working under two different operating systems. He thought it was okay to talk with girls, ex’s, etc. as long as he knew nothing would come from it and he would never follow through or have physical contact. I decided to believe him and try to trust what he was telling me. Fast forward to today- I found out that during that year – he wasn’t just texting one girl inappropriately. but it was many many girls. I am angry again- I feel like I have to reprocess everything – because it does change things. ( This is not a great example – but I explained it to him this way. “Obviously killing someone is a horrible crime, but if you then found out that a person didn’t just kill one person but that they were a serial murderer…that does change things somehow.) Bad example I know…but it was all that I had at the time! lol
    He feels he is being tried for a second time for the same crime. That all of this happened before “our talk” and that he has been operating under my “our” operating system. I feel so many things…hurt, betrayal and so much more. Our wedding is planned and suppose to be August of 2018. Please advise! He says he has done nothing inappropriate since our previous talk and that he wants to spend forever with me and that he is sorry he disrespected me…
    Any advise would be appreciated ! Thanks!

    1. anonymousse says:

      So, in January, he either lied or hid the truth from you further.
      You now know he was sexting many women behind your back, and was lying or otherwise minimizing his behavior.
      Are you sure you have enough trust in him to get married? I think you should postpone and go into couples counseling.

      He’s the best guy who treats you better than you’ve ever been treated, but-he was sexting other women, many other women, at the least, behind your back and lies to you. And could still be lying.

      1. anonymousse says:

        He’s not sorry he disrespected you. If he had been, he would have told you the truth, all of it.
        He’s only sorry he got caught.

    2. Oh, man, this guy is a smooth f’ing operator. He had that perfect answer prepared: the first part, you need to know, is word for word what every guy in this situation says when caught… and then they do it again. The second part is just pure smooth-as-silk manipulation. What a load of BS, different operating systems my ass. 9 out of 10 chance he’s still doing all that stuff and worse, just hiding it better. You should ask him to hand over his phone because frankly you need to see what’s in it because your trust is badly shaken. See what he does.

      1. I mean, if sexting lots of different women while you’re in a committed relationship with the expectation of monogamy is part of your “operating system”, then you deserve to be dumped right quick. It’s not like a preference for the way you put on the new toilet paper roll.

        I’m really trying to imagine how you kept a straight face. “Sorry baby, I just didn’t KNOW that I shouldn’t talk about sex with other women behind your back!”

    3. LisforLeslie says:

      Let me get this straight:

      He didn’t know that texting other women with sexually themed messages is wrong? And you believed him?

      So now you’ve caught him lying and you want to know what to do? YOU KNOW WHAT TO DO!

      Here’s how I see it: He was getting his ego stroked outside of your relationship. Had you not found evidence, he would have continued. He started with general contact. Then he started with flirty texts. As long as you didn’t know he would have continued to escalate until he was balls-deep in someone all the while telling himself that “it’s fine as long as my gf/wife doesn’t know”.

      This “operating system” line is nonsense. When you are with the right person you either don’t want someone else OR you love your person enough that you won’t do things that would hurt them. He shouldn’t have to change for you. It’s not on you to change him.

  27. Avatar photo Skyblossom says:

    If he had just been following a different operating system you would have known all about it because there would have been no reason to hide it. The fact that he hid what he was doing tells you he knew that what he was doing was a deal breaker. So he did it secretly.

    I don’t see how you can marry someone who was secretly sexting with many other girls. What you know beyond a doubt is that he is great at keeping secrets he knows are deal breakers. If you don’t trust him you need to leave him because you can’t have a good marriage without trust.

    He was in trouble for one crime and then you find out he committed lots. The trouble for one doesn’t cover the trouble for all of them. It’s like if someone robbed a store and got sentenced for it and then when they were approaching time to get out on parole it was discovered they did a large series of robberies. They still get tried for all of the other robberies and they don’t get out on parole.

    1. Anonymous says:

      While I do not condone or approve as to the extent of his continuous communication with his ex, I can’t help but to call her out for initially looking at his texts which is a sign of distrust. If you go searching you’re usually going to find something. Just because she did does not justify the means.

  28. mellanthe says:

    This man is a liar, and I don’t think he could ever be trusted.
    1. he and his ex had their chance a couple of times and broke up. The decent thing would be to move on.

    2. looking at texts is a sign that something is wrong, or that suspicions have been raised. I don’t agree with it, but I can see why someone with severe suspicions would need proof – I just point out that having such serious suspicions often dooms a relaitonship before you even find evidence. But I don’t agree ‘if you go searching you’re usually going to find something’ – if a partner was honest and appropriate with their exes or friends, there’d be nothing to find!

    3. He has been telling her she is the one, making sex jokes and flirting etc and reassuring her that you don’t matter for literally the entirety of your relationship. That must hurt so much. I don’t think I could ever trust a man after that, whatever he said. This isn’t a one-night stand or a moment of weakness (and I;d struggle to trust a man after that too), it’s literally many times he told his ex that you mean nothing to him. You deserve better.

  29. Miss Chicka says:

    I think it’s in her best interests to leave. I don’t think this man respects her and if she continued in this relationship her self esteem would take a hit, time, energy, and money would be lost.

    She should start packing now rather than salvage. The respect isn’t there.

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