Emails with an Ex

I have an old high school boyfriend I’m still in touch with once a year or so: a few emails go back and forth with newsy updates, and then that’s it for another year or so. I’m glad we’re in touch: for a few years after we broke up we couldn’t talk without fighting, and so we stopped talking, and I liked that a lot less. He was my first serious boyfriend and we dated for almost two years, and I’m interested in the occasional updates on his life/wife/kids, and I like feeling like the kind of person who can be friendly with an old boyfriend. Plus, occasional contact with him reminds me how extremely not sorry I am that we broke up (he’s a little dumb).

If you’re in touch with an ex, and they make a negative remark about their marriage, how do you react? My rule of thumb OVERALL for emails to an ex (even with no remarks about the spouse) is to make my entire email completely readable by the ex’s spouse AND by Paul: like, I do a final proof-read thinking to myself “Would it be okay if his wife read this? if Paul read this?” and making sure the answer is a definite, obvious YES. (I do make exceptions to this overall policy at times, but I want them to be exceptions I’ve thought about, not oblivious ones.) So if my old high school boyfriend makes some small complaint about his wife, I’m inclined to answer something like “Oh, I am DEFINITELY with your wife on this one,” or something jokey.

But if an ex says, as part of a newsy update, that he thinks his 20-year marriage is probably ending, my usual light/jokey approach doesn’t work. Also, just for further information, this is an ex who called me the day I was getting married to ask me to not get married, saying he’d send me a plane ticket to come be with him, which is the sort of thing that can seem romantic in movies but truly stupid in real life. [Kerry had a good question for clarification: this was my FIRST wedding, the one where I was 20 years old. It was a long, long, long time ago.] This is also an ex who long ago used to periodically float stuff about how wouldn’t it be crazy if we ended up together when we were old and widowed. He hasn’t done much of that kind of talk recently, and it didn’t seem like he was serious even at the time (he’s the kind of guy who loves silly romantic pop ballads and Oprah specials about high school sweethearts reuniting), but I still felt it was better to err on the side of fully squashing it each time by saying very direct things such as “Even if we were both available, I wouldn’t want us to date; it is enormously clear to me that we were not a good match.” And when he would say things like “Imagine if we’d gotten married!,” I would say “We would have had two kids and then a very messy divorce, and we’d still be fighting now.” Anyway. Just so you see why I want to be extra careful about stuff like this with him, even though it might not still be an issue.

Possible reactions I’ve considered:

1. No reaction. Just answer everything else, leave that part alone. He  said it very casually, and it was hard to tell how serious it was, and he didn’t give much to go on.

2. Saying I’m sorry to hear that, paired with a hope that things will work out. (I go with “things will work out” because it sounds like a hope for the marriage to continue, but still applies if the marriage ends: I do hope things work out, one way or another. I didn’t like when I was getting a divorce and some people acted as if it were a giant tragedy and that the only positive outcome was staying married.) Maybe add on something nice about the wife and their relationship? Like, “I’m sorry to hear about you and Steph, and I hope things work out. From what you’ve told me, it’s always seemed like you were good together.”

 

Hm. I like the last sentence of the second option from the “imagining the wife reading the email” point of view, and from the “it’s CLEAR I am not hoping they split up, or in any way encouraging it” point of view—but it seems like saying more than I know; and also, if they’re not good together, who cares if I wrongly thought they were? Still, if I imagine being the wife reading that response, I like the way it makes it seem as if he’s been telling me good stories about her over the years. And I really HAVE thought they sounded good together: even his occasional complaints about her made it sound to me as if she was well able to deal with his nonsense in a way that could only be good for him. But maybe it’s better to stick with sorry/hope, to avoid seeming like I’m pressuring him to stay in a bad marriage. Or maybe this is all kind of complicated and it’s better to go with nothing.

61 thoughts on “Emails with an Ex

  1. HereWeGoAJen

    “I’m sorry to hear that but you both seem like good people who will make the best decisions you can.” Does that work? I had prewarning about a friend who was going to tell me about a divorce (a mutual friend told me, the divorcing friend told me at our next meeting) so I had time to plan out my response. I went with something like “we are sorry to hear that but we trust you guys enough to know you are making the best decisions for you.” Or something like that. I was sitting on the Little Mermaid ride at Magic Kingdom.

    Reply
  2. Mary

    I like your 2nd option better. I might say, ‘I am sorry to hear that and hope things work out for the best’ and leave it at that.

    Reply
  3. Chrissy

    Personally, I find it’s best to stick with hopes for healing and peace no matter what happens, and express sorrow for the loss. I lost a few friends of a certain faith when I announced my divorce and they responded with “I’m praying for a reconciliation.” Um, no thanks? Not that you would do that, of course. So I would go with a brief, “I’m sorry to hear that. It must be difficult for you and your family” and then move on.

    Reply
  4. alex b

    I have so much respect for you, stranger, via your wonderful blog, so I’m gonna be blunt: I would get out of this friendship.

    “I like feeling like the kind of person who can be friendly with an old boyfriend.” — This is not a good reason to stay in touch with someone hung up on you and vulnerable.

    “Plus, occasional contact with him reminds me how extremely not sorry I am that we broke up.” — He doesn’t feel the same way. He’s fantasizing about ending up with you. He has repeatedly made this clear, even if he hasn’t done so recently.

    This is too fraught. You’re his Daisy (from The Great Gatsby). Literally, Daisy had Gatsby’s letter on the night before her wedding, same as you with the call. You’re Daisy, he’s Gatsby, Paul’s Tom. You end up staying with Tom, and Gatsby fares poorly. Your squashing language was excellent and clear, but you’re maintaining contact. And now wading into supporting him through a possible divorce! He’s holding onto hope aka the green light.

    What would I recommend doing at this point? Say some version of, “I’m so sorry you’re going through a hard time with Wife. I think you and I should not stay connected going forward, but I wish you the best.” Then block him on every media.

    Reply
    1. Kerry

      “I’m so sorry to hear that you and Martha are struggling,” casually, in an email that is dominated by mundane news updates, possibly casting Paul in an extra positive light.

      I think including her name breaks down any compartmentalization he’s trying to achieve, and not expressing any hopes or additional understanding helps shut the door on the idea of you as a source of emotional support. Imagine the most unfulfilling person you’ve ever sought sympathy from, and be that person.

      I can also see the logic of just cutting off contact – but I think there’s a chance that the inappropriate hints stopped a long time ago, and maybe it feels cruel or dramatic to cut off a pleasant acquaintance and dramatically raise the bar of appropriateness during what’s probably a really difficult time for someone whose social skills seem not great. Making a commitment to be aggressively boring might work just as well.

      Reply
      1. alex b

        He’s not casual and is going to read into everything said. He’s not going to be turned off by boring stuff because it’s still attention.

        Let him rely on other people around him to get him through this, not the ex he has been building a fantasy life with all these years….

        Reply
        1. anonhere

          Speaking as someone who also has an ex-boyfriend who stays in touch and who does not feel as enthusiastic about that as Swistle … truly, I would prefer mine never emailed me again and for roughly the reasons described in this comments thread, though, equally, the actual emails are pretty mundane and infrequent … short of ghosting the person entirely (or saying, “I never want to hear from you again,” which — I haven’t) I’ve found the “ditching him” thing remarkably difficult. Over 2 decades after the breakup, he still emails me around my birthday and then occasionally at other times. I acknowledge the bday one (and write one of my own to him around his, which is tedious as his bday is about a month after mine and at that point I’ve already given him the one year update in my reply to his) and try to ignore/minimize the others. And generally try to grey rock him (you can google it … polite, boring, unengaged) but to no avail (he persists).

          And yes, tedious, but, again, hard to put a stop to unless one is really determined which I, apparently, am not — so I empathize with Swistle here.

          Reply
    2. Swistle Post author

      What? No no no. Cutting off all contact in a giant scorched-earth gesture, just because in his once-a-year, perfectly-appropriate, newsy email he mentioned that he might be getting a divorce, is not an option on the table, and seems like a really weird overreaction to me.

      Reply
    3. Adi

      I lean this way as well. Being friends with an ex is good if you both view it the same way. If you don’t? It’s so so so bad.

      Reply
  5. Maree

    I think my response would depend on the context of his comments. Was it ‘just letting you know about a big thing that is happening’ or was it ‘just floating with you that my marriage might be ending & testing the waters to see if I have you as a possible backup option’?

    I have seen people who wait to have a plan B in place before leaving marriages. If you think there is any chance of this (and I presume he was married when he made the ‘when we are old’ insinuations) I would be sure to go with the ‘sorry to hear, hope you work it out’ option. I would also be extra alert for any approaches and shut them down a little harder than normal.

    I would also consider looping my spouse in with the conversation in a casual way. I would do this because it feels different to be talking occasionally with a happily married ex, rather than a currently ending marriage ex. That might not be necessary for your relationship but I’m imaginging that if I was Paul I would want to have that information.

    Reply
    1. Swistle Post author

      It was hard to tell. It didn’t SEEM hinty; if he hadn’t been an issue in the past, I probably wouldn’t have thought anything of it. It was more like “Here’s how this kid is doing, here’s how that kid is doing, here’s about the pandemic, marriage is struggling so could possibly be moving, recent health stuff, recent job stuff.”

      I definitely agree about telling Paul. I always give him a gossipy little report whenever I hear from High School Boyfriend, but this news seems particularly important to relay.

      Reply
  6. Lisa Ann

    Red flag warning: do not, I repeat, do not acknowledge. For that matter, do not respond to email. Or any future correspondence.

    Reply
  7. Meredith

    “I’m sorry to hear that and I hope things work out for the best” – simple and neutral but kind.

    I am FASCINATED by him calling you up ON YOUR WEDDING DAY. Like, did he think he was in a John Cusack film? Sir.

    Reply
    1. Kerry

      Also, this seems like an overly gossipy question, but….which wedding day? Ex-high school boyfriend tried to talk you out of a marriage that didn’t last in your early 20s has a slightly different feel than ex-high school boyfriend tried to talk you out of the marriage you’re still in after you’d been broken up for nearly a decade.

      Reply
      1. Kerry

        Sorry, I am now overthinking this…do you and Paul have the type of marriage where you could credibly get away with Paul responding to the email? I’m imaging something like

        “Hey this is Paul – Swistle asked me to check her email because she’s been so busy. Dude that sucks about you and Martha! Hope it works out. I’ll let know Swistle know about Olivia’s piano recital. She always likes the stories about your kids.”

        It’s probably a ridiculous idea, but I was trying to imagine the most disappointing response to a hinty email, and that’s what I came up with.

        Reply
        1. Swistle Post author

          Ha ha ha NO, I do not have the kind of marriage where it would be okay for Paul to go into my email and answer it for me!

          Reply
      2. Swistle Post author

        Oh, yes, good distinction: it was the first-marriage-at-age-20 wedding he tried to talk me out of.

        Reply
        1. Bitts

          I’m going to join the chorus saying to just stop responding. This relationship is not mutual – it sounds like there’s a squicky undertone to the interactions, given his history of making borderline-inappropriate comments. It’s flattering to have someone who carries a several-decades-lobg torch, but to do so is immature and inappropriate on his part. A divorce is a hot fire. It burns if you get too close.

          Reply
  8. Caz

    This is a very strange world we’re living in and I’ve been trying to give everyone an extra amount of grace about things right now. Despite past history, maybe he’s just casually mentioning the idea to try out what it feels like to tell someone that. Much like people come out to casual strangers or acquaintances before their friends/family, or tell someone inconsequential that they’re pregnant before the recommended 12 weeks. So they don’t need to reel back later to close friends and say “oh, never mind”. Particularly if we’re not in much conversation with strangers/casual acquaintances, you could be that person for him.

    Regardless, I think your approach of “could his wife and/or Paul read this” is a good one and I’d keep it at that. I also like the suggestion of using the wife’s name, whether or not you go with option 3. It does add a lot to the casual and uninterested vibe.

    Reply
  9. Liz

    I agree about telling Paul.

    As for your email to your ex, “I’m sorry to hear that you and Pauline are having a rough patch. My best wishes to you both. I hope it all works out.”

    And then mute him. Because I agree this feels….on the edge.

    Reply
    1. Shawna

      I am perhaps disproportionately tickled that you gave the ex’s wife the feminine version of Paul’s name, as if all spouse pseudonyms should be a version of “Paul”!

      Reply
        1. Liz

          It was the most neutral name I could think of, especially in the context of wanting both Paul and ex-boyfriend’s spouse to be able to read anything you wrote.

          Reply
  10. Jackie

    Co-signing everything Alex B said. It doesn’t sound to me like you get a whole lot out of this relationship but I guarantee you he is absolutely feeding off every iota of attention you give him. Do what Alex said. Except don’t say “I think we shouldn’t be in contact…” – instead say “I do not want to be in contact with you, please don’t contact me in the future.” Don’t apologize, don’t hedge. You can be kind and sympathetic but don’t leave any cracks in the door. Captain Awkward probably has something in the archives on this topics with some good scripts. If he contacts you after that, then he gets one reminder that you said you didn’t want to be in contact anymore. Again, no apologizing. After that, you never respond. You don’t pick up his calls and you don’t listen to his voicemails. His emails get filtered straight to the trash and any physical letters get marked RETURN TO SENDER in Paul’s handwriting. Unfriend him on social media. And then you stop wondering about him and let him fade. I’m so sorry, it’s hard to end relationships under any circumstances.

    Reply
  11. Cara

    Yeah, I’m definitely not the “stays in touch with the ex” type. I had one that was a friend for a lot longer than he was a boyfriend, and we stayed in touch for a couple years. We drifted apart naturally and I like it that way. My husband was definitely the stay in touch type until an event similar to your wedding day call. That didn’t end well.

    That said, after all these years I don’t think you need to end contact before there’s an actual inappropriate event. What would you say if you were in a bookclub and a casual acquaintance tossed out a comment about her marriage being on the rocks? I would probably say something like “oh man, that stuff is always tough. Good luck figuring it all out.”

    I wouldn’t just ignore it, though. That’s a pretty big thing. Maybe just said it because pandemic isolation is hard and they were having a bad day . But I don’t think you can assume that, and it would be callous just to ignore it.

    Reply
  12. SheLikesToTravel

    How does the initiation of the annual check in commence? Does he reach out and you follow up? Or did you reach out and he responded? If it is the later, maybe don’t reply at all this time. You can reevaluate how to proceed a year from now.

    Reply
  13. Tessie

    In the last few years, I’ve implemented a policy of trying to be neutral about divorce news ( e.g. “oh, ok!” /”oh, I hadn’t heard that”), or at least not offering condolences. For one, I was not the least bit sorry about either of my divorces, and two, it leaves the conversation open to letting the person tell YOU how they feel about it, and not how you think they should feel. BUT. This works better for in-person conversations! What would be the email equivalent?! Ugg, I’d probably just ignore it.

    Reply
  14. JMV

    I don’t think this kind of news should be ignored. I also don’t think it rises to the level of totally cutting him off either. Option 2 seems best if it were me.
    I still keep in contact with a college ex who called me wasted on the evening of his bachelor party. We had a stern conversation about that and have had pleasant conversation appropriately every 6 months since then. I enjoy the kid/family updates.

    Reply
  15. Laura

    I also still keep in very occasional contact with an ex. We keep up like I keep up with other college friends. I would respond to his news about his marriage in the same way you would respond to an old but not very close friend telling you about their marriage. Perhaps with something like HerewegoAJen mentioned. I would keep the tone exactly the same as always, and maybe tell a nice story that emphasizes your family happiness.

    Reply
  16. Jane in Pa

    I have kept in touch with several ex’s over the years. Mostly infrequent social media, one lives in the area and we have mutual acquaintances, so occassionally, our paths cross and it’s totally fine. Boundaries appropriate. Husband aware and fine.

    I wouldn’t immediately jump to a cut off. I would say: I am sure you and wife will figure out what is best… and leave it at that. Let Paul know as FYI. If any of communication continues and sounds like he is fishing, inform Paul, set the boundary with ex immediately. Keep it short and firm. Anything inappropriate after that, you don’t respond because he did not respect your boundary.

    Hope he was just filling you in and nothing more.

    Reply
  17. BKC

    I have one ex that I still end up texting with every two or three years. I too, like the thought of being a person that can stay friends, since we were such good childhood friends for years before this failed relationship. I genuinely wish him well. We live in the same town. But every time we text I’m happy for about 10 messages and then it’s stilted and weird and I think, “Whuuut do we have in common anymore?”

    I think if he mentioned the end of his marriage I would ask him how he feels about it, let him vent and then say I’m rooting for him to find happiness. And then faaaade out for another two years.

    Reply
  18. Jodie

    My husband is friends (And in infrequent contact with) with a woman that he was really good friends with in high school and has admitted to me that he wished it had gone much further and that it probably only didn’t because he was clueless. From the spouse perspective, I can say your reading the emails as if spouses are reading is really good because it helps you to make sure nothing can be inferred. I’d probably go with the Oh I’m sorry to hear that I hope everything works out with the added commentary about the wife and move on to another topic.
    Probably also I would not ever at this point say anything negative about Paul. In fact for this email I would not complain about any domestic unhappiness not even aimed at the children, cats or house. He may still harbor feelings for you but you don’t seem to reciprocate those feelings and it sounds as if you have been really careful to not give the impression that you do. In other words, I don’t think you are leading him on in any way.

    Reply
  19. Nicole MacPherson

    HE CALLED YOU ON YOUR WEDDING DAY AND ASKED YOU NOT TO GET MARRIED. Wowwwwww.
    I am not in touch with any of my exes, mostly because the relationships exploded in such a way that I would never want contact again. However, I have had male “friends” from my past message me on facebook and I do like to think, would I be okay if my husband read those? I like the #2 response the best, for what it’s worth.

    Reply
  20. Shawna

    To my surprise (because I think the tendency is to assume everyone is like oneself) I seem to be the odd one out here. I have a number of friends now that I dated in high school and it’s never occurred to me to “manage” their relationships with me differently than any other relationship. They’re simply friends, and frankly some of my oldest, best friends, and my husband and I enjoy and appreciate the company of them and their spouses. This includes one that I’d dated in high school and had impassionedly declared years later that he was still in love with me and always felt we were meant to be in each other’s arms when we were 80. But I said I didn’t feel the same way, and he went on to meet and marry a lovely, smart woman and have a family and we all get together occasionally and enjoy the heck out of each other.

    High school was a long time ago and we’ve all moved on. In fact, one of my exes from my 20s ended up as a roommate of my husband’s and mine for a few years, and my kids call him Uncle Bob, and he and my husband are much close friends than he and I are.

    I’m not trying to brag here, and there are exes I’ve lost touch with, and one ex with whom I exchange Facebook messages about once a year like Swistle does (a couple extra this year because he’s Canadian living in California so I wanted to check in on how he and his family are doing during the pandemic). I’m just saying that there appear to be many ways to interact with exes and I really didn’t know that usually these relationships have to be managed so carefully. For the record, I’m on team, “I’m sorry to hear you and Pauline are having some issues. These times are definitely difficult and can make everything harder to deal with, but I hope things work our for you both.”

    Reply
    1. Kerry

      I agree except the “we’ve all moved on” part because I also totally have an aunt who was my uncle’s high school girlfriend and then just “happened” to join his church 20 years later when they were both having marriage trouble. Some people have not moved on and their spouses should not be shamed for noticing and worrying about it. I think everyone just needs to be honest with themselves and their significant others about their own emotions, whether that means admitting that an ex high school boyfriend is more annoying than anything else, a completely platonic friend, a harmlessly fun reminder of the intense emotional connections and giddyness of being a teenager, or an actual threat to your ability to function as a responsible adult.

      Reply
      1. Shawna

        The “we” wasn’t intended to be generic – I meant specifically me and the old boyfriends with whom I’m now friends have moved on. I certainly hope I didn’t come across as intending to shame anyone!

        I know a couple of people who dated in high school, split up, met and married and had families with other people, but eventually divorced and ended up back with their high school sweethearts – in one case it was after retirement and his high school girlfriend had always wondered what had happened to him and hired a private investigator to track him down. Clearly she hadn’t moved on! And apparently neither had he, as they’re now, as seniors, living in New England, raising horses, volunteering for Habitat for Humanity and running an online shop for imported British puddings!

        Reply
        1. Kerry

          Yeah sorry…I can totally see that it wasn’t a generic we. And I appreciate you speaking up for non-managed friendships with high school boyfriends. I actually do tell my ex (although it feels ridiculous to classify him according to the 5 months we dated when we were 15 instead of the 20 years we have been friends and not dating) things I would not want my husband to read, because he’s one of the few people who’s known both of us well enough and long enough to be counted on to have empathy for both of us when I need to vent. Everyone, including my husband, is just going to have to trust me that this isn’t step one to me wanting to run away with him. (And my husband does! Jealousy works in some marriages but I really appreciate the lack of it in mine.)

          Reply
          1. Shawna

            Yes, exactly! There’s definitely a point at which the friendships outweigh the brief romantic entanglements long ago if you bothered to stay friends after breaking up in the age of no internet or email or smartphones). Staying in touch back then took effort. For me, dating someone for a year in high school just doesn’t really even get much thought compared to 30+ years of being friends since then. I don’t think of them as my ex-boyfriends, I think of them as my friends and may only rarely spare a moment to remember that we happened to date long, long ago, in a high school far, far away.

            The exes I’ve lost touch with are the ones who it turned out were kind of assholes that I wouldn’t want to be friends with, or the ones who married partners not like yours or mine, i.e. they didn’t want their spouses to stay in touch with people they used to date (or in one case, pretty much anyone he associated with before she came along). I too appreciate a jealousy-free marriage!

            Reply
  21. Jenny

    One thing I notice here is that maybe the level of friendship he thinks he has with you is different than the one you think you have, or want to have, with him. If your marriage were struggling, is there any chance your ex is one of the people you’d tell? He may just think you’re closer than you are. That happens a lot in friendships without there being any hinting involved. I’d just keep the friendship at the level you want it, not the level he wants it. Perfectly healthy. You got this.

    Reply
  22. Alice

    I think it would be weirder for him to not mention an impending divorce than for him to not mention it, given the type of communications you’re describing. And it wouldn’t necessarily mean that he’s telling you in the hopes that you’ll reconsider him as an option or anything. It would mainly mean that you’re clued in on what’s going on and aren’t surprised when he quits talking about her entirely or when he talks about visitation with the kids (if they’re still at an age where visitation happens).

    I would just go with saying something like you always regret hearing about long marriages ending and that you hope he and she both find a way to be okay and get along with each other as things go forward. And just be yourself, communicating how/what you always have. If he starts communicating more than usual or sending signals that he’s building something in his head, you can always nip it in the bud as you’ve done before, direct him to online dating, and– if needed–hit the pause button on contact for a while.

    (You could also tell him that you hope he’s getting counseling, which I personally think is a good idea for anyone in a divorce situation. And which, unfortunately, is advice a lot of men are unwilling to even hear. I know a number of guys who would pause communications in response to hearing “counselor” just to prevent themselves from hearing it again….)

    Reply
  23. Alice

    Wow this comment section has been a real rollercoaster to read through! I agree that it feels a bit soon for the scorched earth approach but also (like you suggested) would steer far clear of any comments possible to be interpreted as even mild unhappiness with your current situation. Like Caz mentioned I think it’s common to give big (or hard) news to people who are not invested in the situation first – I know I certainly do that.

    Reply
  24. AnnabelleSpeaks

    I would probably say something like “I’m sorry to hear about the possible divorce, that sounds really hard, especially during a pandemic when everything is so strange generally.” Basically I would respond to it as I would have if he had NOT had the hinting/wishing/asking you to abandon your wedding day stuff in the past. Since it’s been a while since he did that and you seem to be generally fine as distant penpals now, I’d give him the benefit of the doubt. I think if I read something like that between my spouse and an ex I’d be fine with that. If he escalates it and makes any actually hinting suggestions in another email then I’d immediately shoot it down, but so far if he hasn’t done anything wrong in this specific interaction, and if the more recent interactions via email in recent years have been problem-free, he might be just a friend updating you now.

    Reply
  25. Susan

    I can’t imagine wanting to stay in contact with an ex in any way, shape, or form and and see zero upside to it. And there are many downsides – hurting now partner, having to navigate how to engage, devoting a non-zero amount of time to thinking about the topic.

    I don’t get the point of any communication.

    Reply
  26. Jenny

    So I’m reading a split in the comments between people who think saying this to someone is Earth-Shaking News And Also Probably Means You’re Available, and people who would email this news like 1) pandemic grocery shopping, amirite? 2) oldest is into politics now, super weird 3) I’m probably getting divorced 4) youngest has braces, check out pics!

    The reception of the email probably depends a lot on the tone!

    Reply
    1. Swistle Post author

      YES: his email was totally: news about kid #1 (and asking if I wanted to weigh in, because that kid is having an issue dating someone from a very seriously Christian family, as he knows/remembers mine was), news about kid #2, what their city is like in the pandemic, complication of possibly moving elsewhere because marriage not going well, how that might affect kid #2’s next school year, update on health issue, update on job. It is impossible to imagine replying to that with “NEVER SPEAK TO ME AGAIN” and a full block of all contact!

      Reply
      1. Jenny

        Yes, it’s one of my personal rules to live by (along with Don’t Fuck With the Deep Ocean and Always Bring a Book) : Context is Everything.

        Reply
  27. Debbie

    Well I surely understand how you might want to stay in touch and on good terms if possible. I’ve had a similar casual sporadic email exchange with an equivalent ex, and it was fine as long as I maintained my boundaries. (He died a couple of years ago, maybe that’s making me soft.) Mr Ex doesn’t sound that crazy obsessed to me (more recently, anyway) on the information given, he sounds more speculative and maybe lonely, in a way that maybe could be managed with the trusty aforementioned boundaries until he partners up again, which I’m betting he will. I could be wrong and of course the speculation could snowball given any little bit of encouragement. I realise this isn’t an answer to your question! I think you could do the: Sorry to hear that, I wish you and Pauline all the best. The thing is to remain sturdy on your line if he does any more casual testing of the ground.

    Reply
  28. Ali

    It sounds like all the inappropriate stuff/him being hung up on you was WAY in the past (like prior to his marriage). If so, the scorched earth approach seems like overkill to me. I would just respond very minimally “I’m sorry to hear that, I hope that you guys work it out in whatever way is best for all” or something along those lines.

    If his inappropriateness was post marriage, that might change my answer but I would hold his nuttiness 20+ years ago against him.

    Reply
    1. Swistle Post author

      YES—all of what I consider the Major Stuff (like where I had to tell him NO, SERIOUSLY, NEVER) happened before he was married and before I was married to Paul. He’s made various flirty remarks from time to time since then, but always what I think of as crossing my own subjective line for what I’d like him to say (because of really wanting to keep this friendship truly above reproach), without crossing any sort of objective line. That is, some of the stuff I’ve nipped in the bud have been things I think would be fine for other exes; I just really want to be careful.

      Reply
  29. sooboo

    There are people who stay in touch with exes and people who don’t and no in between. I am of the no reason to stay in touch type of person but my husband has stayed in touch with his first serious girlfriend. I tend to think there is usually one person in the equation who is still carrying a torch and it seems like your ex probably is, at least a little. You have excellent boundaries so it’s harmless. If he stepped out of line I have no doubt you’d shut it down. My husband’s ex was the torch carrier and was mildly inappropriate until she got married and now there’s an occasional Facebook comment and that’s it. Your number #2 comment sounds perfect.

    Reply
    1. Swistle Post author

      I think I am a good example of an “in between”: I maintain a friendly and pleasant friendship with this ex-boyfriend, but haven’t spoken to my first husband at all, not since even before our divorce was final, and I don’t want to.

      Reply
  30. Ruby

    My first reaction to this post was “Time to cut ties with this dude”, but after reading it a second time, I don’t think that’s necessary. If he’s backed off from the initial inappropriate behavior, and you enjoy the annual emails, and your desire to maintain casual friendship outweighs the potential awkwardness…then I don’t see a reason not to keep the friendship at its current level. I’d reevaluate things if he suddenly wanted more frequent contact, or if he started making suggestive comments again – but it doesn’t sound like that’s the case.

    As for what to say, I think I’d go with something along the lines of, “I’m sorry to hear about you and Steph. Best wishes to both of you, however you choose to handle things.”

    Reply
  31. Meg

    For what it’s worth, I like “oh no, that sounds really stressful” or a similar general response, because you’re not saying hey you should stay married, and you’re not saying hey you should definitely break up.

    But I do realise you’re not taking votes for how to respond!!!

    This seems quite complicated.

    Reply
  32. Carrie

    I think option 2 seems to be best.

    While I agree that cutting off all communication is not warranted in this situation I have to admit that your description raised alarm bells for me and it looks like many others. I wouldn’t completely dismiss those alarm bells. It sounds like this man has crossed appropriate boundaries multiple times and I am assuming that some of those occasions were after you were married to Paul and he was married to his current wife. If it had been 10 years since he had made any inappropriate remarks I assume you wouldn’t be so concerned about making sure there was no room for misinterpretation of your response. When I read “he hasn’t done much of that kind of talk recently” my brain assumed that maybe he has done SOME of that kind of talk recently, or said some things vaguely enough that it at least made you wonder.

    Anyway, I’m not saying this to critique your writing – I LOVE your writing and think you are one of the smartest most emotionally intelligent people I’ve had the pleasure of reading. I say this because your first instinct with this man seemed to be “I need to tread lightly with this person” and I think you need to trust that instinct and not talk yourself into thinking this man has 100% innocent motives when that has not always been the case over the years. Trust your gut.

    Reply
  33. Anna

    This whole situation makes me uneasy. I agree that an abrupt cutoff of communication is unwarranted, and I think it would actually encourage him, if that’s what he’s looking for. He clearly subscribes to the “women play hard to get” school of courting. If you want to maintain contact, it sounds like you have the right detatched tone in mind, but I would also be mindful of WHY you are maintaining contact. Is it to be a supportive friend? Is it because you are flattered by his attentions? Is it to watch the potential train wreck from a distance? None these reasons are mutually exclusive.

    Reply
    1. Swistle Post author

      No no no—it’s that I like being in occasional touch with him and hearing occasional news of his life, just as I would with other old friends from high school! And we’ve been doing that successfully for well over two decades now! Dropping the friendship as soon as he mentions marital trouble (as if it’s suddenly inappropriate to maintain the usual friendship, if he is not happily married) seems really weird to me.

      Reply
      1. Kerry

        1) People vary WIDELY in the extent to which they either toss everything that happened during and shortly after high school into a bucket of “Who even remembers that stuff?” or all of those things are remembered very clearly and continue to seem potentially relevant to this day.
        2) People vary WIDELY in the extent to which they see a woman having an email conversation with a married man – whatever their history with that man – as something to handle with extra amounts of caution and tact out of deference to the wife

        I think the combination of those two things is throwing people, with things being remembered very clearly and the desire to proceed with caution and tact being interpreted as VERY SIGNIFICANT. But maybe it’s actually just being detail oriented?

        Reply
  34. Slim

    As someone who is in touch, to varying degrees, with some of her ex-boyfriends and not in touch with all of them, I am glad people aren’t holding any decades-old weirdness against me. Current weirdness is an immediate disqualifier, but come ON, how can any longtime readers of Swistle worry about her ability to understand the nuances of language?

    Reply
  35. Kate

    If his divorce discussions have progressed far enough that he’s making finite plans to move to another city, there’s a good chance that he’s understating how far along that decision is, not fishing for reaction. Lots of people use language imprecisely, and “my marriage isn’t going that well” could actually mean “we made a firm decision to end this”. It would be more weird, in that context, for him NOT to mention it.

    Reply
  36. Squirrel Bait

    Huh. I read this post and the comments with some fascination. I am gay-married (as the kids call it) to another woman, and I am still close friends with an old (queer, female) friend for whom I use to have very, very strong feelings. (We never really dated, but it was close enough.) The friends-with-an-ex thing is incredibly common among queer people as there just aren’t enough of us to be able to go around salting the earth every time something weird happens. I also think that one should generally not be held accountable for dumb, awkward things one says or does before, oh, age 25.

    I’m glad that this level of contact has been working for you and that any weird vibes you were getting from him are in the distant past. It sounds like you have a good sense of where your own boundaries are and that you are conscious to hold onto them even if he were to try to breach them in the future. It also sounds like you are extremely clear with yourself and with him that you are not interested in re-kindling anything, now or ever. So in that case, I think you should feel free to say whatever you would say to a casual old female friend in this situation. I’m a fan of, “Sorry to hear that, hope things work out in whatever way makes sense for the two of you.” But then this is coming from gayland where the rules might be different, based on the strong reactions some people are having above, so maybe take my advice with a boulder of salt.

    If you have already sent the reply, disregard all this and maybe give us an update!

    Reply

Leave a Reply

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

This site uses Akismet to reduce spam. Learn how your comment data is processed.