“Am I Letting My Siblings’ Engagements Ruin My Relationship?”

I’m a 31-year-old female in a five-year relationship with a 28-year-old man with whom I have lived for the past three years. For the first couple of years, he brought up marriage frequently and how much he wanted us to build a life together. It freaked me out a little early on because I wasn’t there yet, but I could still definitely see myself marrying him one day. Then this talk cooled, and life marched on. The most “life building” we’ve done is getting a cat together.

Fast forward to last year, and his younger brother gets married. Then my sister gets engaged, followed shortly by my brother. I’m super happy for them, but I can’t help but feel a little sad that I’m not there yet. My boyfriend and I have been together longer than either of my siblings have been with their significant others and only slightly less long than my boyfriend’s brother has been with his. I didn’t bring up any of this, but my boyfriend came to me and nervously “joked” how the pressure was on. I told him the absolute last thing I want is to be proposed to under pressure. I said I only want him to propose if he really, truly wants to marry me and thinks I’m worth it. He was relieved. He even said he was glad they got engaged, because now that gives him “another year, at least.”

Now as my siblings’ wedding plans progress, so do my worries about our relationship. I find myself scrutinizing my boyfriend daily in my head, getting frustrated over his lack of career (he hates work and has no ambition to do more with his professional life), his willingness to quit things early when things get tough (he left college when he was one semester away from graduating), his social anxiety (he can’t be anywhere crowded or he becomes beyond unpleasant), his frequent money management issues (I bail him out all the time), and even his relationship with his mom (I actually love his mom, but I do feel like she coddles him too much). I know I’m such a jerk for thinking this way, and I hate even more that I’ve become less attracted to him as a result of it. I know I’m not perfect either, and I keep trying to remind myself of that, but it’s not helping much. I wish I could go back to just loving him blindly.

With my siblings’ marriages pending, I just know that we’re going to have to fend off a lot of “when will it be your turn?” My family adores him, so I know they’d definitely like to see it happen. But at this rate, I’m now worried that if it ever does, it’ll be because he felt pressured and not because he genuinely wanted it. Am I just overthinking because of my siblings’ situations? Or, is my relationship doomed? — Stressed and Sad

You, like a lot of people in your position who’ve been in a relationship for a while and are watching their peers get engaged, get married, essentially move forward, are asking the wrong question(s). The two explicit questions you ask here get close to the real question but don’t hit the bull’s eye, and the implicit questions you’re asking are completely wrong for figuring out what it is you want to know.

Explicitly, you’re asking whether you’re overthinking things because your siblings have recently gotten engaged and whether your relationship is doomed. I don’t think you are “over” thinking anything, but it’s not a leap to say that your siblings’ recent engagements – to people they’ve been dating less than you’ve been dating your boyfriend – have triggered some contemplation on your part about the state of your own relationship. And if you’re thinking about your relationship through the lens of “why are we not engaged yet?”, then wondering whether it’s doomed isn’t such a leap either, especially if there are no signs of forward movement. In fact, your boyfriend, by saying that these recent engagements have bought him “at least a year” to put off proposing to you is suggesting that any forward movement is still a ways off.

It’s understandable, given all this, that you’re questioning your relationship. The questions you’re posing, though – to me, but most of all to yourself – are not the ones that are going to get the crux of the issue here. Instead, I suggest you ask yourself whether you want to build a future with your boyfriend, whether you want to spend your life with him. You focus a lot on your boyfriend’s feelings about proposing, and about your own feelings about his proposing – you don’t want him to feel pressured, you want him to propose because he wants to marry you, because he thinks you’re “worth it.” But what about your own feelings about getting engaged? What do you want?

As you think about these questions, I want you to pay particular attention to two things. The first is the issues you outline in your third paragraph. Your boyfriend isn’t perfect and you have a list of the things that you don’t like about him. But no one’s perfect, right? So that brings us to the second thing I want you to think about, especially in relationship to all the issues you have with your boyfriend: Is he worth it? It’s a question you ask about yourself in relation to him. You want to feel “worth it” to him. And I think of that term in two ways, and maybe you do, too. First is the idea that we all have value, and you would hope that in your partner’s eyes your positive attributes exceed your negative ones so that you are of high value to him, an asset in life and in love.

The second way I think of the term “worth it” is whether a relationship is worth the energy it takes to “make it work” and move it forward. I can’t tell from your letter how hard either of you is actually working at your relationship, and maybe that’s part of the problem. Maybe you’re both in a holding pattern, withholding the effort it takes to move a relationship forward, because neither of you has decided whether the relationship is “worth” the energy it would take to move it forward: the sacrifice; the self-reflection; the honest and open communication; the compromises; the giving up of certain fantasies to embrace the reality – fully embrace the reality – of the person you love, limitations and flaws and all.

The question is not whether you are “worth it.” The question is not whether your relationship is doomed. It’s not even whether you’re overthinking things simply because your siblings are recently engaged. The questions you want to ask yourself are whether you want to marry your boyfriend and whether the relationship is worth the effort it would take to move things forward to a place where a marriage could be successful and happy. You can answer “no, not yet” to the first question while still answering “yes” to the second, and you can spend a while actually putting effort into your relationship to see if the answer to the first question changes. But if it doesn’t, or if your answer to the second question is “no” already, I think it’s pretty safe to say that it’s probably time to MOA, move on already.

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


  1. It sounds like your bf is not someone you should marry, unless your goal is to marry someone who is to immature to take up the normal responsibilities of a modern human and would rely upon you to support him and insulate him from the world. Sounds like your world would slowly shrink to match his and you would end up respecting him less than you do today. You seem to be clinging to this relationship out of a sense of urgency to be married fast.

    Yes, he has definitely cooled on the idea of marrying you and probably on you. Your relationship growth over your time together is a cat?

    It seems a slam dunk decision to MOA. Re-read your letter. You point out a lot of quite bad things about him. I don’t recall you saying anything positive. If you make a plus column and a minus column out of what you wrote, the answer should be obvious. Inertia is not a life plan.

    1. Yep, you need a pro/con list. Instead of resenting other people’s engagements and marriages, think of them as a prompt, bringing clarity to issues in your relationship that you were previously content to overlook.
      Also, wtf is this?: “He even said he was glad they got engaged, because now that gives him ‘another year, at least.'” Another year to do WHAT?
      As my grandfather always said, “If you don’t know where you’re going, any road will take you there.” You need to decide if you’re going along for the ride.

  2. Wendy’s advice is spot on – you’ve been dating someone a long time and you’ve been patiently waiting for them to grow up and be your definition of adult (like being able to manage finances). And at the same time, you’re waiting for their approval. It sounds like there is a serious imbalance of affection and dedication in this relationship.

    If you moved on, would he miss you or would he simply miss the things you do for him?

    What do you want in a partner and are you getting it? Does he make you feel secure? Valued? Appreciated? Can you live with this person as he is with no changes? If yes, then stay – but if you think he’s going to change… then you may need to MOA. You can’t count on it and you can’t make him change.

  3. You seem to think because you’ve been with him a long time it makes sense to get married. But should you? You said you’re less attracted to him and you basically carry him because he’s lazy. You’re already over it, how is marrying him going to solve any of these problems? He’s draining you, financially & emotionally. I hate the “tradition” of only the man deciding when to get married. The woman just waits patiently till he feels like it. I do NOT think you should marry this guy, I’m just ranting about my engagement pet peave

  4. brise romande says:

    I think that you are wasting your time. Your relationship goes backward. When a couple lacks common projects, usually, their relationship ends. I can’t identify any common projects here. On the contrary, it is difficult to imagine a more unromantic declaration than his reaction to the everybody-is-getting-married-round-us situation. He is avoidant with you like with the rest of his life. The question is: why do you stay with him? I think that if you really wanted to marry him, you wouldn’t have given such an answer – a self-defeating answer to a man you say you love. If you wanted to get married with him, you would say so, especially when you are asked about it (however awkwardly). You could have said, hugging him: yes, when do we do it? … and discussed the idea with him. But you avoided it, as if he were the only person to get a vote in the situation, as if it were given that you only wait the HE proposes. No, the reality is: you are unsure and somehow unsatisfied and distrustful of his ability to function, be an active and reliable part of a couple, potentially a family if you want to have children. So you transfer the responsibility on him and wait and wait. You can wait ten years like this. And why does your family love him? One wonders, reading your post. Just own your own feelings and make a choice yourself already. Address the issues with him and if he is still reluctant or unable (he seems to have mental issues) to build realistic plans with you as partners, end it. By the way, you are doing with him exactly what you reproach to his mother. Why do you need to nurture an avoidant immature guy? That is an other real question you should ask yourself. My guess: you are avoidant yourself and can’t make a decision on your own. So do it. Make a decision.

  5. It sounds like you want to get married to your boyfriend because you’ve sunk a lot of time into the relationship and think it is the next logical step to take in a relationship. I don’t think this is uncommon. Somewhere around 30, a lot of my friends started getting engaged and I felt like I was falling behind the curve because I was single and, of course, the common commentary we hear from the people around us can make us feel under pressure that only really exists as much as we allow it to. I know it can be tough to tune out, though.

    By your account your boyfriend is:
    – Unmotivated/unambitious
    – Gives up easily
    – Socially unpleasant
    – Bad with money (of all things listed, this would be my biggest concern)
    – A big baby/momma’s boy

    You’re right that we all have flaws and there will always be some kind of catch, or however you want to put it, with any partner we could possibly have. But assuming nothing about your boyfriend or relationship ever changed, would you be okay with that forever? Better to be honest with these things now than after tying the knot.

    1. I think the mismatched ambition is a huge red flag. In my anecdotal experience, when partners have very different levels of ambition it invariably breeds resentment because one person is shouldering more responsibility. It’s not just about job/career ambitions. A stay at home parent can be just as ambitious but focused on parenting, community, social life, home care.

  6. Avatar photo MaterialsGirl says:

    LW: it doesn’t need to be this hard to be with someone and make progress in your relationship. Getting engaged or married isn’t the end goal, it’s just a step toward combining your lives and your future..
    I too thought i had to marry the person I had sunk years, tears and beers into. It was the wrong move.
    I ended up marrying someone MUCH more quickly after starting to date them because we talked about where we wanted it to go, we weren’t on the same page/timeline at first, but I told him what I needed to make a decision and we went from there. But the progression felt natural, rather than pulling someone to get there.

  7. To those calling the boyfriend immature:

    Marriage takes two. It’s a partnership, not a gift bestowed by the man once the relationship passes some arbitrary marker in time. He was enough of an adult to approach her about her feelings. She played coy, letting him believe she was happy with their current status, instead of facing the issue or discussing it further.

    1. He’s not immature because he doesn’t want to get married now. He’s immature because LW says “his lack of career (he hates work and has no ambition to do more with his professional life), his willingness to quit things early when things get tough (he left college when he was one semester away from graduating), his social anxiety (he can’t be anywhere crowded or he becomes beyond unpleasant), his frequent money management issues (I bail him out all the time), and even his relationship with his mom (I actually love his mom, but I do feel like she coddles him too much). ”

      LW asks if she should just go back to loving him blindly. No, not possible. You can’t unsee these negative traits nor forget your judgment of them. He’s a manchild.

    2. LisforLeslie says:

      I’ll give him props for having the conversation while the LW sits and waits to see if she’s “good enough” for him. That is her immaturity/insecurity talking. But he didn’t bring it up because he was thinking “I would like to discuss future plans” he brought it up because he moved the goal post. He’s deferring any decision for another year out of some pretend politeness when in reality, he probably can’t/won’t make a decision that’s too “skeery” .

  8. You didn’t write one nice thing about your boyfriend at all. I went back and checked.

  9. When I started reading this letter, my first thought was, “Wow, you need to actually have a serious conversation with him about marriage.” But as I read further, I realized that’s premature. You first need to have a serious conversation with yourself about whether you really want to marry this guy or whether you just want to be married and he’s currently the only option. Or whether you feel like you’ve already sunk so much time and energy into this guy that you have to stick it out now. Both of these are terrible reasons for getting married that will only lead to a lot of misery for you both.

    Yes, everyone has flaws, but this guy’s particular flaws put an enormous burden on YOU. His lack of motivation, willingness to quit when things get tough, and financial ineptitude mean that you can’t count on him to be there for you in times of need, and that he may in fact end up creating crises that you have to bail him out of. That’s not a nice way to treat your partner and it’s not even remotely surprising that it’s damaging your attraction to him. Loss of attraction isn’t something you do intentionally and it doesn’t make you a jerk. It usually means there are deep problems with the relationship. And the attraction will not return if the problems aren’t fixed.

    So here’s my question to you. If none of those things about him changed, ever, would you be excited — not willing, but genuinely excited — to marry him and commit the rest of your life to him? Because you can’t make him change, and it doesn’t sound like he has any desire to change on his own. You can have a conversation about these things, and what you need and want out of a relationship. You can ask him to do those things. But honestly, if you have to ask over and over, or if he says he’ll do things differently and then repeatedly doesn’t, there’s no magic way to make things change. You can leave and find someone more compatible with you, or you can stay and resign yourself to being unhappy.

    And maybe stop looking at his mother’s coddling as being about her behavior and recognize that he’s allowing it. As a fully fledged adult, I’d be mortified to have my parents taking care of me. I take pride in paying my own bills, doing my own chores, buying my own toys, and that I was able to help my parents out when THEY needed it rather than the other way around. I want to be with a partner who does that as well. And I suspect you do, too. Sadly, this guy ain’t it.

  10. I wish someone had told me this before I got married: if he’s bad with money now, that’s not likely to change, even if he gets a large increase in salary. And if you’re married, his debts are your debts. That may not be scary now but think about it in, say, 20 years. I found out my ex had racked up credit cards with huge unpaid balances, the house was in foreclosure (we were 9 years in on a 15 year mortgage), he’d taken out a loan on his car, and the IRS garnished the entire contents of our joint bank account. He had all the bills routed to our (cash) business so he could hide all this from me. Like your bf, his mother coddled him, he was immature and rarely finished what he started. None of this happened overnight and it was definitely incremental but it started out with him needing $200 for a car payment after a few months of dating…

    Believe me when I say: MOA! Run now before you’re married with kids and stuck! And don’t look back!

  11. It seems the LW is stuck in a sunk cost fallacy. Otherwise why would she still be with him? Why would she sign up for a lifetime of bailing him out financially and dealing with the mismatched ambition?

    Inertia can be a powerful, terrible thing.

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