I (34/f) am concerned about my relationship with 40/m due to his insecurities.

We’ve been dating about nine or ten months, and we met right after my divorce was finalized at the end of last year. I’m happy to be in a relationship and I love him, but I’m obviously not trying to rush back into marriage or anything. For right now, I’m just enjoying his company and trying to keep a slow and steady pace.

However, orange flags keep popping up, and they all center around his insecurity about our relationship or him getting cheated on. He admitted that he’s run into that in past relationships, and so I want to be sensitive to that – he clearly has some trauma over it, and I can understand because I’ve been there. However, it’s affecting our relationship because he will get very anxious or upset about something for what feels like no reason. A few of the issues:

* I didn’t post a pic of us on Facebook quickly enough for his liking, effectively announcing our relationship. I don’t use Facebook frequently anyway, and I didn’t even announce my divorce. He’s met my close friends, so the fact that he was hurt by that felt very strange to me. He’s met the important people! And goodness, it’s just social media. But I did it to make him feel better, even though I was deeply uncomfortable with it. It’s important I guess to some people, so fine.
* He’s admitted he’s gone through my list of Facebook friends and casually asked which guys I had dated. I told him, and he was very uncomfortable that an ex boyfriend from college would periodically message me memes (like once every few months, and I barely engaged in the conversation). While I don’t necessary agree with this, I can somewhat understand it and agreed to just ignore future messages. I’ve ignored those messages since out of respect to my boyfriend. This one I can at least understand.
* We had a conversation about sexual partners and body count early on. We were both honest, and he said he appreciated my honesty (the number isn’t low) and was glad I had experience! He said he was surprised that I’d be so open and forthcoming about it. We then got into a conversation about a girl he knew who slept with 50 people in one year, and he was completely disgusted by this and felt she was morally bankrupt. I was shocked – what does her sexual history have to do with anything, especially when he’s slept with WAY more people than that?? How does it happening in one year make a difference? I called him on this because it felt like a major double standard, and then the conversation turned to him becoming really, really anxious and asking if this is something I would do if I was single. I wouldn’t, but not because I think it’s wrong to do. I’m just old and lazy and that’s a lot of work. He admitted that he was afraid that someone who would do that would cheat. I think that’s ridiculous – how is it okay for me to have a high body count over time, but someone who did it in a year is morally bankrupt? What’s the difference? I’m mostly concerned that suddenly it became about me and what I would do. Like, he brought this girl up – what does that have to do with me and why are you asking me about a situation that isn’t going to happen?

So it’s little conversations like this that separately aren’t a HUGE deal, but when I look at them together, it concerns me greatly. He also doesn’t acknowledge that his reactions could be problematic – it just seems like his position is that he feels how he feels. He clearly has some trust issues and fear of infidelity and getting hurt, which I understand. At the end of the day though, there’s nothing either one of us can do to prevent the other from cheating. I trust him, and if he cheats, well then he does and he sucks, but I can’t spend my time worrying about it. I would hope he’d give me the same courtesy.

Also, we’re in our 30s and 40s – I feel WAY too old to have conversations like this about social media and him drill me over what I’d do in completely hypothetical situations. This feels so immature, and I am getting to a point where I feel like he either needs to address this in therapy or I need to leave. And no, I don’t think this is a case of he doth protest too much. I think he’s had poor past relationships with lots of drama, and because there’s no drama here, he doesn’t know what to do with that. When I casually ask him how he feels about us, he says he feels so secure and is so happy, but his behavior indicates the exact opposite. I try really hard to show and tell him how much I care to help – he acknowledges that he feels so loved, but then he’s anxious again.

So I guess my question is just that – how do I address this when he doesn’t feel like it’s a problem? He feels how he feels and there’s clearly reasons behind it so I want to be sensitive to it, but I’m feeling uncomfortable about how much I have to reassure him in various ways, which feels performative to me. I show and tell him that I love him and he says he feels so cared for, but one small conversation about a hypothetical situation or something from our past will derail him completely, and I’m tired of picking up the pieces and acquiescing to him so he doesn’t spiral. If I don’t respond the way he wants me to, then suddenly it seems it’s a reflection of my character and then he becomes super concerned. And I don’t know how to explain that just because I respond differently doesn’t means he should be concerned.

TL;DR: I’ve (34/f) been dating this guy (40/m) since the end of last year. He’s kind and thoughtful, and I do love him. However, he seems very insecure about our relationship in a way that I don’t know how to address. I’ve reassured him, but at the same time, this feels very much an issue he needs to work out in therapy. He feels how he feels, but how do I explain that how he feels, frankly, is not something I can fix, and it’s doing damage to our relationship?

8 comments
  1. I think you need to put it in those words. His feelings are valid, but they aren’t yours to resolve. He needs therapy (I think everyone would benefit from therapy honestly) and he needs to stop leaking his insecurities all over you because it’s a turn off.

    It’s harsh, but if he can’t handle it then that tells you a lot about what a future with him is gonna look like.

  2. It sounds like you are at the point where it’s fine to just lay it on the line the next time an issue crops up (or even before an issue arises). Let him know that this pattern of insecurity feels a little immature, and it’s hurting the relationship and how you view your future together. If he’s not willing to address it by changing behaviour or seeking therapy, then this is probably not the guy for you.

    Ultimately, it seems like you want more maturity in your relationship. I am dubious that it will happen with this guy, so you might have more luck moving on, but you can try talking about it more overtly first.

  3. I can’t imagine being 40 and going through someone’s near-dead facebook account, scrutinizing their friends list, and complaining about not being featured on it. Not only that, but all of that sounds like a symptom of his issue. You could probably post your professions of love to him on facebook every day, and it still wouldn’t be enough.

  4. I don’t think these are orange flags I think they’re red flags.

    He’s a hypocrite about sex – this strongly suggests a level of misogyny or at the very least magical thinking. Unless he understands his perspective is wrong and decides to address it in therapy it’s gonna come back to bite you. His attitude will breed resentment and fear in him about your sex life.

    He feels entitled to comment on benign social media activity and ask you to alter your behaviour to address his anxiety.

    He doesn’t see anything wrong with his behaviour.

    I suspect he will see any approach as an attack and a validation of his anxiety – you threatening to leave him over what he feels is reasonable behaviour. The only thing you can really do IMO is stop soothing him. Stop engaging and making concessions and stop letting him make these things your problem. Tell him ‘I acknowledge that you’re uncomfortable but I’m not going to (do the thing you want or keep talking about this) because I haven’t done anything wrong. I’m going to (leave or end the conversation) now.’ and then suggest he talk about his anxiety with a therapist.

    He’s gonna spiral hard because he’s used to you managing his anxiety for him. Either he’ll do irreversible damage to the relationship or he’ll get a wake-up call.

  5. I feel like you’re spending way too much time and effort, considering _both_ your ages, on soothing him. What work is _he_ putting in to self-soothe and get over his hangups? And by “work” I mean standards he holds himself to and actively confronting his anxiety, not something he guilts you into doing.

    >I feel like he either needs to address this in therapy or I need to leave.

    You are right. You have no business being punished for his exes’ actions, or judged in comparison to _the other kind of woman_ (the one who slept with 50 people in one year, whom your bf is disgusted with).

    >one small conversation about a hypothetical situation or something from our past will derail him completely

    All I can see is that he tries to rile himself up and upset himself so that you can jump to comfort him.

    >If I don’t respond the way he wants me to, then suddenly it seems it’s a reflection of my character and then he becomes super concerned.

    Yes, the way you respond _is_ a reflection of your character — the problem being that if it’s something he doesn’t like, he tries to get you to change it instead of learning to deal with his own emotions.

    I think this relates to some bigtime anxiety on his part. He needs things to go according to the script he has in his head, and will have meltdowns if reality veers ever so slightly off his course. He believes that anything that doesn’t behave according to his plans must be corrected — including you. But you aren’t responsible for his mental health, and it sounds to me like he needs to spend quite some time in therapy to realize how he’s shooting himself in the foot by acting like this.

    This is the complete opposite of facing his fears; it’s yielding to them.

    >how do I explain that how he feels, frankly, is not something I can fix, and it’s doing damage to our relationship?

    You simply tell him: the condition for you two continuing to date, is him going to therapy. He is free to refuse, and in that case you are free to end the relationship.

    ETA: you mentioned in a comment that he’s started going to therapy. That’s good! But things won’t change overnight, he won’t wake up one morning and see “his anxiety being connected to his insecurity”. It’ll take a long time and he will need to put in genuine effort.

  6. the part where you said that a comment or conversation about your past will de-rail him completely and that you acquiesce so he doesn’t spiral.

    this is not a behavior you want to deal with in a relationship.

    im wondering – were your family or ex manipulative and exhausting in this manner? is this a mode of conflict that you’ve accepted in the past? eggshell walking & the inability of the other person to self-regulate and accept responsibility for their behavior?

    Stalking a partner’s FB/Insta/TikTok understandable. I do it. lololoo I would never admit it, much less ask him about his female friends or our “status” ( a decade and hes still single on FB and so am I) because im not in seventh fucking grade.

    relationships shouldnt be that much work, esp the first year! this is the honeymoon – whats the next few years gonna be like?

  7. >I think he’s had poor past relationships with lots of drama, and because there’s no drama here, he doesn’t know what to do with that

    I have anxiety and this is pretty much how it works. Like this year I resolved a situation that was a cloud hanging over my head, I don’t have anything anymore to really stress out over. Everything’s fine, its fine! But I don’t really *believe* its fine and I find myself stressing out over shit that I didn’t anymore because surely there’s still stuff to worry about, I’m just not seeing them and they might pop out at me at any moment. Like I need to go to the dentist and I keep procrastinating because surely my teeth are a lost cause and the dentist will yell at me, right? In reality, I probably just need to get my wisdoms removed and maybe a few fillings, but until the dentist tells me that’s all it is, I won’t believe it.

    And I’ll tell you, I think when you’re anxious about unrealities, like you being unfaithful or not as committed because you’re not posting on an account you don’t even use, you might say something like “okay I get that you had bad relationships before, but the fact is I just don’t use facebook and when I do, I don’t use it to post much about myself.” and I think that’s all you really owe someone with anxiety; respect that they have anxiety, but you don’t need to indulge in it. When you change your behavior to address it, the unreality becomes reality. You validate his feelings *and* agree implicitly that he was right to be concerned about it and your behavior needs to be modified to correct it.

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