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Dear Captain,

I’ve have a friend (female late 20s) with whom I’ve known since college. We have lived together twice in our 20s once in college and now again in our late 20s. I’ve always known this friend to be somewhat worried about spending money and partly that’s why we became friends in the first place, since we both come from modest backgrounds and entered a prestigious college where everyone else seemed to be awash with money. At the time this wasn’t apparent to me why we were friends but now it makes sense, it felt comfortable and familiar and there was a shared understanding of our difference from everyone else.

Fast forward and now both of us are in our late 20s and I end up living with this friend during the pandemic. We both have good jobs now and earn decent money. The thing is friend hasn’t seemed to move past the fact that we can spend money now and enjoy life. Her life is controlled by saving and scrimping on the smallest of things despite that fact that she could very well afford not to. Every thing is brought back to money to the point where I feel it’s really impacting the atmosphere living here and I resent her for it.

While stinginess is probably only a symptom of a wider issue in general about our friendship and changing values, Im planning on moving out because of it. I’m not sure if I’m overreacting by moving out and possibly ditching a friend I’ve known for years because they’re tight with money? I feel she has no other friends. She also sees me as a close friend, while I have many other friends who I am much closer to.

Suffocated with Stinginess


Dear M,

Hello and thank you for your question!

For me, this question seems to be about the difference between identifying your own reasons for making a decision and informing the other person about (all of) those reasons. You worry that you might be “overreacting” by moving out, and you frame moving out as potentially “ditching a friend,” almost like you think that you’re not allowed to move out unless you can make an airtight case about why, and to do that there has to be a villain somewhere. You’re even willing to cast yourself in that role if that’s what needs to happen to make the break.

It  doesn’t have to be like that. Relationships can change shape and even end without anybody having to be the villain.

I think people sometimes do a lot of unintentional damage when they don’t think they are allowed to leave a situation or set boundaries just because they want to (“Am I overreacting?”) and as a result they try to pathologize or villainize the other person until they find – or manufacture – sufficient justification to actually react. The more afraid they are of conflict, the longer they tend to procrastinate until some outside event forces the issue, and the more likely it is that what comes out is a hurtful explosion of All The Reasons You Suck, All Of The Time, Forever, instead of stuff like “Hey, you probably didn’t know, but that’s actually my umbrella.” While the self-doubt-avoid-avoid-avoid-avoid-avoid-avoid-avoid-avoid-over-justify-EXPLODE cycle keeps advice columnists in business, it is otherwise no fun.

So, let me start with an important reminder: Letter Writer, you are allowed to leave a living situation that is no longer making you happy for one that you think might make you happier, just because you want to. This is true at any age, but your late 20s is an especially good time to recalculate and reimagine what happiness looks like for you and make changes accordingly. I absolutely believe you about how annoying and suffocating you find your roommate’s behaviors about money, and the fact that it probably feels 1,000 times worse inside her head to be like this doesn’t mean that it’s not affecting you. (Ever had a roommate decide to actively make their issues into your issues, by, say, scrutinizing every bite of food that goes into your mouth and delivering a real-time calculation of how many calories is in that, to the point that you start eating secretly, standing up, in your closet, only when she’s asleep? No? Lucky you! ) Letter Writer, even if your friend were the best roommate ever, “I would like to live alone/with different people next time around”  and “I would like to spend less time with someone who stresses me out”  – truly!!!!! –  are good enough reasons to seek other arrangements.  If you can accept that, then hopefully it will empower you to be gentle with everyone, including yourself, and realize that maybe you don’t have to kick so hard when you swim your way free.

As the person initiating the household split, you currently have a head start that temporarily grants you a little bit more knowledge and power than your roommate. I suggest using this advantage to clarify what you truly want out of the looming conversation about dissolving your little household, so that you can be strategic about what you say.

Here are some questions for you to think about before you speak up:

A) Is your main goal to end or dramatically scale back the friendship? Does that need to be an explicit break-up conversation, or will moving out and reducing your day-to-day proximity accomplish that on its own over time? Forced proximity is part of what’s killing this friendship now, but is proximity necessary for its survival in the first place?

B) Is your goal to unload your frustrations about your friend’s relationship with money and how that affects you?  Do you want to express a bunch of anger you’ve been holding onto for the sake of keeping the peace? Do you want your friend to understand what she’s doing to annoy you, “learn a lesson” about that, and/or change her attitudes and behaviors as a result? If so, are the tensions and conflicts about money part of an ongoing conversation you’ve been having all along? If you actually shared your reasons, would they be a surprise to her? If she promised to change how she interacts with you about money, would it change your mind about wanting to leave? (I’m guessing no, but it’s good to spell that out).

C) Or, is your main goal to let your roommate know that you intend to move out of the apartment and have that all go as smoothly as possible, with minimal immediate disruption to the friendship? Is the “right now” conversation about your plans to move, with figuring out how to stay friends more of a “later” project when you have your own space and hopefully her attitudes toward money and other daily little tensions will be less of an issue between you?

D) While we’re asking questions, are there any safety concerns you have about moving or telling this friend you are moving? It doesn’t sound like it here, but I have personal experience moving out in secret while a roommate was out of town out of realistic fear that she would harm my stuff, my pet, and myself if I told her while she still had access to all of those. I sincerely hope this doesn’t apply for you, but I suggest doing at least a quick audit of how much this person could mess with your important papers, prized possessions, pets, mail, credit history, and digital security if she got Big Mad and taking steps to protect yourself. If everything turns out fine and you never needed these precautions, it’s okay, she’ll never know you made them. But if there’s even the slightest hint you might want them, a very good time to put them in place is right now, *before* you tell her.

All of these questions are part of your overall decision and the fabric of your relationship with this person, but not all of them are necessarily “right now” questions. In other words, all of your accumulated reservations and annoyances about your roommate’s tightfistedness can be true, but not all of them are equally useful, depending on what you want out of this negotiation.

As with other break-ups, assuming that this isn’t a violent, “get out NOW” situation, I’d like to make the case for Option C) above. Once you’ve decided for sure that you’re leaving,  communicating your decision and your plan for the future is both more useful and kinder than placing blame, excavating the conflicts of the past in an attempt to sell the other person on why it’s their fault that you gotta go, or pretending that there’s something they could do to convince you to stay. Once a relationship ends, however painful that process may be, everybody gets to be free from working on the relationship anymore, including talking through and attempting to resolve every problem, including making sure the other person “learns their lesson.” (Whether you quit a job or got fired, you don’t have to provide free employee retention consulting your way out. Other people’s epiphanies get to be their own business from now on!)

Meaning, practically, that once you’ve decided to move out, all you really have to say is: “Friend, when our lease is up, I am planning to get my own apartment. I wanted to give you plenty of notice so that you can make good plans for finding a new roommate or moving somewhere else when the time comes.” 

If you are in fact moving to a place by yourself, that can be your reason all by itself. “I’ve never lived alone as an adult and I want to give that a try.”  If you’re planning to move in with different roommates, that’s a slightly harder sell (roommate-feelings-wise), but not impossible. “Friend A & Friend B invited me to take the extra room in their place and I’ve decided to take them up on it. I wanted to tell you right away so that you can find a new roommate or situation that works for you.”  

Once you deliver the news, your roommate will likely have some Big Feelings, and her initial reaction might not be awesome. Or then again, it might be something like “Phew, I’ve been thinking of moving too, and I didn’t know how to bring it up!” You don’t know! So probably don’t add a lot of “You probably won’t want to hear this…” or “I know I’m officially your Only Friend…” baggage or assumptions when you deliver your news. You can’t control her reactions, and doing too much to try to manage what you assume her feelings will be in advance is going to backfire, badly, and make you come across as incredibly condescending. (Even if you’re right, nobody ever thanks you for making correct assumptions about their bad behavior in vulnerable moments, like, “It’s amazing how right you are about this thing that just hurt my feelings and destroyed my life, great job!”)

That said, since time is on your side, you can certainly anticipate likely reactions based on what you know about her and make plans for how to respond if that will make it easier for you to maintain your boundaries. If your roommate perceives you moving out as a rejection of her (not…untrue?), if it brings up a torrent of financial anxieties about how she’ll afford a new place (neither surprising nor irrelevant), if she didn’t see this coming at all and feels blindsided (reasonable!), what first comes out of her mouth might be pretty volatile and tailor-made to provoke you in return. This is where your strategic planning about what you’re actually trying to accomplish will come in the most handy. You don’t have to respond to everything she say or solve all of her problems before you’re allowed to move to a different apartment!

If she asks why you’re leaving, try to keep the answers focused on yourself. “I’ve been thinking about it, and I think I want to live alone for a while.”  “I’m ready for a change, and since we have to inform the landlord if we’re renewing or not, this seems like the right time.”  Reasons that are about her = more reasons for her to justify or argue about. If your mind is made up, this is a waste of everyone’s energy and way more likely to hurt than help.

By staying focused on what you want (moving out), communicating what you’ve decided to do about it (move out, effective [date]), and staying secure in the fact that you are ultimately going to get what you want and need no matter how she responds right now (to have moved out), and keeping that separate from making any value judgements about her, then you don’t have to use your history of annoyance with her attitudes about money to make your case. You don’t have to make that case, or ANY case. That’s good, because there’s really no way to say “I find your obsession with thrift suffocating and want to be done now” that won’t be received as an existential attack on What Kind Of Person She Is, consuming your entire friendship in an ever-burning fire of remembered insecurity, trauma, and resentment.

You’ve had a while to think about all of this, but she’s just learning of it now, meaning you can probably better afford to be a little bit generous. Her first, surprised reactions are not necessarily the most important ones, so if you can grant both of you a little time, a little grace, and a little of what friend-of-blog S. Bear Bergman calls “selective amnesia,” then you can let her have whatever feelings she has without escalating or trying to talk her out of them in that moment. You can tell her that you understand that she’s not happy about the news and suggest taking a break from the discussion to think and cool down before discussing timing and logistics.

Once you’re not living together anymore, you might find that you actually get along with this friend much better. When you’ve had a little time and space for your spending habits and financial priorities to be 100% your business, without commentary from her, and without feeling like you have to manage her feelings about any of it, you may remember all the things that you actually like about her. Then, if you want, you can invite her to inexpensive hangouts when that works for you and save fancier plans for friends who are more compatible with you around money. If money is still an ongoing issue between you, then you can talk about it without it being part of your inescapable, daily grind. If it doesn’t work? Then it doesn’t work.

The friendship may end when the living situation does, or the potential for greater peace and harmony in this longtime friendship *may* come with time and space, there’s no way to decide or really promise that right now until sufficient time and space have been applied and had a chance to work their healing magic. I think your best chance to buy everybody as much of that time and space as possible is to be very direct and stay very focused on moving out as the logical, happy, exciting  – and non-negotiable – next step for you.  None of this is about punishing her, fixing her, or fixing the friendship, it’s about where you want to go from here. You’d like to move out, and you want her to know so that she is free to make plans for what she wants to do next. The sooner she knows, the more time she has to save up. The sooner you decide, and decide to tell her, the sooner you’ll be free to see what else is possible.

I hope it goes as well as can be and that both of you find happier and more compatible living situations very soon.

Dear Captain,

My MIL has always been very nice and welcoming to me, although I don’t feel particularly close to her. Lately I have been driven to distraction by the way she seems convinced that she will live forever. She is turning 80 in June, and she is in only okay health. Every time we Zoom with her or see her in person (frequently, as we have a young and adorable grandchild), she makes some statement that presumes she’s going to be in great health for at least another decade. Just today, she was talking about volunteering at the hospital, and it was “some people find the palliative care department upsetting, but I’m fine with it–maybe in another 10 years it will hit closer to home!” She has literally said “I’m going to live to 97” multiple times in my hearing.

I’m sensitive about this because my own father died very suddenly seven years ago, when he was in his late 60s (my MIL knows this). It feels very clear to me that we all die and it could happen any time, and the way my MIL goes on seems both callous and jinx-y. I get really upset when she starts talking about how little she and my FIL have planned for old age (they’re vaguely thinking of downsizing, their wills are maaaybe updated, and there has been zero discussion with my husband about what they expect to happen to his younger special needs sibling, who currently lives with them). She literally laughs at attempts to discuss this stuff, like it’s a joke.

I don’t want to tell her that this bothers me, because right after my dad died, she did a lot of coming really close and staring into my eyes and saying “you must be so upset about your dad.” I REALLY don’t want to start that behavior up again. My husband had my back about that stuff (and any other times she’s been weird TO me), but for him, my getting annoyed that she thinks she’ll live forever is a me-problem, not a her-problem. Maybe he’s right? I would love for her to take end of life planning more seriously, but really I need a better way of handling my reaction to these constant comments of hers. I don’t just want to start croaking “Death comes for us all!” in the middle of brunch, so what do I tell myself to keep calm?


Harbinger Daughter-in-Law

Dear Harbinger,

I preserved your email subject line as the post heading as it is truly A+ work.

Short answer: No, there’s no way for you to “politely” discuss this with your mother-in-law (MIL) and your husband is probably right about the feelings she’s calling up in you being yours to manage.

Long answer: It’s not that the feelings aren’t valid; there’s so much here about grief for your dad, envy that he didn’t get all these years with his grandchild, envy that she “gets” to be so blithe about all of it, and legitimate worry about how her lack of planning will impact your little family down the road. (Even if the feelings weren’t valid, they are happening, so you might as well deal with them.)

But your husband is right in that your feelings – and whatever actions you take in response to them –  are the only piece any of this that you can actually control. Your MIL is 80 years old. Assume that she knows what it’s like to be elderly, she’s seen what her peers have gone through, she’s opened the paper and seen her childhood playmates in the obituaries section. This also may be her coping mechanism in the face of all the fear and the loss during a mass death and disabling event that is still ongoing. If she’s seeking reassurance? If she’s in denial? Either way, her life and eventual death belong to her, and you’re not going to be able to tell her a single thing about it.

Where I come in, is, if you can’t change the situation, can you make it a little easier on yourself?

With that in mind, I will suggest a few strategies.

1) “Ha, I hope you’re right about that!” 

If your MIL does in fact live to be 97 and maintain enough of her physical health and faculties to spend her time doing all the things she wants to do, wouldn’t that actually be pretty awesome? Can you find a way to wish her the future that she wants for herself, or, at least act as if you do when she brings it up? I don’t really believe in jinxes, but if I did, I’d want her to cheat Death, poke Fate in the eye, and get away with everything. To quote the philosopher Atticus: “I hope to arrive at my death late, in love, and a little drunk.” 

Since these topics and conversations upset you, it’s probably best if you disengage. Cut these conversations as short as you can and make them as boring as possible. Sometimes that might mean absenting yourself, putting your husband in charge of all Grandma Zoom Time while you take a break or get some chores done. Other times, it might mean finding some pleasant and anodyne response to repeat, something that efficiently completes the social circuit in the expected way, removing the need to dig into the topic more deeply. (And then absenting yourself). For this  purpose, I want you to try out something like “Ha, I hope you’re right!” 

Now, there are times when actions like absenting yourself or changing the subject  are meant to actively communicate discomfort, return awkwardness to sender, teach the person a lesson, and/or enforce a boundary. Like, you’ve tried persuasion, it failed, so finally you tell the person, “If you bring up X topic again, I’ll leave.” They bring up X. You leave. They learn that you will follow through, they have a little think, and hopefully change their behavior as a result.

This is NOT that. This is hearing “Maybe in 10 years the palliative care thing will bother me, but you know I’m going to live to be 97!” and you saying, “Nice, I hope you’re right about that!” or “97? May we all be so lucky” or “Only 97? Don’t be a quitter, Grandkid expects you to make it to at least 100” in the breeziest tone you can manage, and then asking if anybody needs anything from the kitchen while you’re up, so you don’t have to stick around for the answer. You’re not trying to jolt her back to reality or correct her, you’re trying to make a socially acceptable dodge. Two entirely different things.

2) Unpack your feelings so they don’t unpack themselves. 

You’re still grieving for your dad. How could you not be? ❤ If you’ve never sought therapy or it’s been a long time since you have, “My MIL is in denial about aging, it’s bringing up all these feelings about my Dad’s sudden death, and I’m also worried about a future where nobody’s really planned for the possibility of getting sick or what’s going to happen to my SIL, by the way, the pandemic is still killing so many people even if everyone is bored with it” is definitely a “big enough” problem to take to a compassionate, neutral listener.

If therapy is not an option, write about it in a journal. Contact a trusted friend you know that you can lean on. Find a grief support group. However you can, get it all out of you in controlled, deliberate ways so that it’s not on the verge of exploding out of you whenever your MIL gets under your skin.

I predict that a lot of stuff is going to come out of therapy (or making a plan to write/talk about it in some fashion), and one thing you’ll be prompted to do is to sort out your own plans for what happens if something happens to you or your husband. Which leads me to  my next practical suggestion.

3) Put thine own paperwork in order.

Work with your husband to make sure that your own wills are up to date, that your plans for what happens to your child are in writing, that you have all the necessary and useful insurances in place in case something unexpected happens to either of you. Think of it as doing the boring, necessary part now, when everyone is able to make decisions, so that you don’t have to invent it from scratch later. You can’t control what your in-laws will do, but you can actually make sure that you’re doing all you can to take care of business.

Going through this process yourselves is the perfect vehicle to talk to your husband about some of your fears about what happens if his parents die or become incapacitated. Do they have plans for his sister? Do they have insurance and money set aside in case they need long-term care or assisted living? Do they have medical directives, funeral plans, cemetery plots, an assigned executor or attorney? Does he know what any of this looks like, or where to even find it? Does he have siblings, and do they know?

If his parents don’t have any of this in place, what’s are the potential costs or consequences to both of you if they die or become incapable of making their own decisions? “If MIL hasn’t budgeted or made arrangements for SIL’s housing and care in case something happens, should we be setting aside $X/month in our budget now? What resources would be available for her care from the state? Can we afford to set aside money for SIL and also build our kid’s college fund?”  Your in-laws plans are pretty much your in-laws business, but there are areas that their choices your husband, and by extension, you and your child.

I think these worries are all sprinkled throughout your “YOU KNOW YOU’RE NOT GOING TO LIVE FOREVER, RIGHT?” feelings when your MIL is breezy about the future, but spelling it out this way gives your husband a foundation for going to his parents and saying,

  • “Hey, Parents, Harbinger and I just did all of our estate planning, and boy did it suck, I get why you never want to talk about it. Still, can you and me sit down one Saturday morning very soon and go through it? I’ll show you our in-case-of-emergency folder, you show me yours, then we’ll put everything back in the drawer and eat something tasty.” 
  • “I know, it’s the worst, but I don’t want anyone to be blindsided the way we were when Harbinger’s dad went so sudden. We want to make sure that we won’t leave an expensive legal mess for anyone, and we want to make sure that we’re able to honor your wishes and make sure that SIL will be okay. If you can take a few hours to show & tell what you have in mind, then we can stop talking about it until you’re 97.” 

He can ask. They can joke, like they always do. He can ask again. “Please, the thought of losing you someday is so upsetting, I don’t want to think about it! But I want to make sure that you can always live the life that you want, right up until the end, and to do that, I need to know some things sooner rather than later.” 

4) Your husband’s family = Your husband’s job to wrangle. 

If you’ve handled your own Scary Unknowable Future paperwork and decision-making to the best of your ability, done your best to wrangle your feelings about your dad, and found a polite, mostly pleasant way to interact with your MIL most of the time, then you’ve done what you can do. The rest is up to your husband. Don’t let this default to being your job, it’s good for literally no one. He is both best equipped and best place to be the parental ambassador to his side of the family.

Oh, before I forget:  It would be okay to admit to yourself and those of us at CaptainAwkward.com that you don’t like your MIL all that much right now and would like to interact with her less, even if she weren’t unintentionally pushing your buttons about this one sensitive thing. It’s great that she’s a nice, welcoming person, but if she’s stressing you out, intentionally or unintentionally, then let her eat crackers for a while! Let your husband take the lead in maintaining that relationship, and tag in when you are actually both willing and able.


I’ve trawled the archives, but I haven’t found anything in the breakups tag addressing the overlap of

1) Nothing is glaringly wrong

2) I live with this person

Also, I’m definitely overthinking this.

I’m a woman who is living with my boyfriend. On the whole, I enjoy dating him and living with him, but I’m starting to think this is not the person I want to be with for the rest of my life. No big flashing GET OUT NOW signs or anything like that, just an overwhelming sense of “this is fine for now, but not forever”.

So, if I know I want to break up with him eventually, is it unethical to stay with him for the next couple of years while he finishes school? He’s a student, and there’s a good chance he’d have to drop out (due to housing instability) if we broke up. I don’t want that to happen. And like, I love this man! I generally enjoy dating him! But it feels… icky to decide to leave and then not Go for another two years.

Agh! What’s the ethical thing to do here?

Thank you ❤

Hello there!

May I issue a the strongest possible recommendation against staying  in a relationship that you’re planning to end for years (!!!)l, without telling the other person how you feel or what you intend. Lying to people you love, purportedly for their own good, in a way that takes away their choices? This is not the way.

When you end an important relationship, there is no perfect way to deliver the news, there is no way to prevent the other person from getting hurt and upset, there is almost never a magic reason you can offer that will make it all right , and there is no way to plan for every possible eventuality. May I suggest the following order of operations, to be adapted as you see fit?

First, I see a lot of worry about how a break up will affect your partner, but almost none about what will happen to you. It’s time for you to daydream yourself into your new life, one where you are only responsible for you. If you knew for sure that you were breaking up, say,  a month from now, what would work best for your housing, education, and career options? What are your emergency funds like? Who could you call on for moral support, a place to crash, and other help? What would make all of this as easy and painless as possible for you? Thinking this all through doesn’t mean committing to any specific course of action, but I want you to remind yourself that you have options before you make any big decisions.

Next, when you’re ready, tell your boyfriend how you feel and give him a little time to react and make his own plans. One kindness you could do here is to take responsibility for the decision and make it as sure and as unambiguous as possible. “I’m so sorry to say this, but my feelings have changed, and I want to break up.When he asks why, do your best to make the “whys” about yourself, and don’t seek to justify it by listing his perceived shortcomings or convince him that this is for his own good. He didn’t do anything wrong, but your feelings have changed. You’ve realized that, while you love him, you don’t see yourself together in the long term. The fact that you want to break up is a good enough reason, you don’t need to manufacture an airtight case to convince him that it’s the right thing to do.

After that, maybe after everyone’s had a few days to process, it’s time to talk logistics: Who moves out, who stays, how and when does that happen? If you need to continue sharing the living space for a while, what are the ground rules and expectations for that? This is where I suggest getting extremely boring and specific, especially about money, space, and time. “For the next two months, howabout I’ll sleep in room A, you can sleep in room B, headphones and/or a closed door on either of our parts means ‘I’m not here’ unless there’s an emergency, we’ll split the bills this way, we’ll both agree not to bring any new partners or dates back here, and we’ll both do our best to give each other a lot of space and be considerate roommates while we find our footing.”  Keep in mind, he most likely hasn’t been doing the same planning you have, so it’s okay if he needs a little time to catch up. When in doubt, “Ideally, how would you like to handle ______?” is a good question to keep things constructive.

Once you’ve made & communicated the decisions, the sad, awkward grieving time starts for both of you. It’s not fun, nor is it avoidable, but also, it doesn’t last forever.

You mention that breaking up and living separately might jeopardize your boyfriend’s housing situation, and that’s not a silly fear. The question “But where will I live now?” will almost certainly come up in some form once he knows you want to leave the relationship. Here’s the thing: You don’t have to have the answer or solve the  problem. Breaking up means recusing yourself from planning the other person’s future. While it may not seem so, living with you is not the only choice he has. Roommates and shared housing options exist, on-campus housing exists, applying to become a Resident Assistant in exchange for free or less expensive on-campus housing exists, taking a semester off to work and save up exists, friends and family exist,* student loans exist (they SUCK, but they exist, and keeping students in school during a reversal in fortune is one of the things they’re actually for). Honestly, now, when he’s a student, might be the time he has the most outside resources and assistance available to him. I don’t know what his exact set of options looks like, and I won’t claim that they are all great compared to the life he planned with you, but I know that your partner had to figure out where and how to live long before he met you, and I trust that he will figure it out now. Of course, if you are in a position to put some “get back on your feet” funds aside for him without jeopardizing your own financial situation, that would be a very kind thing to do, but it’s not a requirement before you’re allowed to sever the romantic relationship.

[*Note: I don’t know if this applies to you, but over the years I’ve received many letters from people who are worried that if they break up, their partner will lose their “only person.” Even if that’s true, and the partner has managed to cultivate and maintain absolutely zero ties outside of the romantic relationship, it doesn’t fall to their soon-to-be-ex to make up for all other people on earth by staying in a situation that they don’t want to be in. In your case, if he’s a good, likable, pleasant guy that you’ve enjoyed dating, there’s absolutely no reason to think he wouldn’t be able to find someone equally great down the road. ]

It’s admirable that you are thinking about how a breakup will affect your partner, but withdrawing from a relationship means withdrawing from both responsibility for and control of the other person’s choices. Being honest with your boyfriend means giving him information that is essential to his ability to make good choices for himself. If he needs to plan for a future on his own, then it’s important that he knows that as soon as possible. Assumptions that he will be utterly helpless without you or that staying with him when you’re secretly planning to be gone is some kind of favor are kind to no one.

P.S. Surprise! Comments are open. I repeat: Comments are open on this post, at least for the next few days.. I want to hear from readers who have experienced Pretty Good Breakups, ones where even though there was crying and moving house and money stuff and difficult logistics, everybody was maximally considerate and kind under the circumstances. What specific thing did an ex do to make life easier for you, what did you do to make it easier for them, and how did it all turn out?

Hi Captain Awkward,

I (she/her) and my partner (he/him) have been planning our wedding for nearly the past 3 years at this point. Pandemic concerns forced us to push it off, but last summer we were finally able to settle on a date (late summer 2022) and booked a venue, multiple vendors, and laid all the groundwork. Partner and I have had much support—emotional and financial—from family and friends with planning this wedding. Ultimately, we can afford to pay for what we want to do, but it is a big financial commitment and our families want to gift us with help so we can save our money for our future married life.

But unfortunately, all throughout last year, my mom began suffering from mental health concerns that have been growing and spiraling out of control. This has been tough for me for many reasons, but primarily because while I love my mom, we have always had a strained relationship. My mom is the center of her own world, and despite wanting to good by others, she is truly unable to understand that other people have different wants and needs than her. She also struggles with low self esteem and projected this onto me as I was growing up. She spent much of my childhood and young adulthood confiding her feelings and struggles in me when I was too young to support her, and often based her happiness on my achievements and whether or not I was doing what she wanted. I learned that I could not be my true self around her because every time I expressed my feelings, she would invalidate me because ultimately, her feelings are more important to her. Additionally, she is often incredibly rude to others and takes her anger out onto others because it is difficult for her to balance how other people feel with her own feelings. It has taken a lot of therapy for me to be able to set better boundaries with her in order to maintain a relationship with her, and more importantly a relationship with my father, who is truly my hero.

Speaking of my father, he is currently taking care of my mother throughout this current crisis. He is a fixer and is always trying to do whatever will solve the problem right in front of him. And the current problem is that my mom now will not be well enough by the summer time to attend my wedding. In January, my mom asked partner and I to consider postponing until she was better. Partner and I were both incredibly upset that she would ask this because at the time, there was no timeline for when better would be. We had already committed to the date and paid for many things and while both my parents offered to recoup all debts incurred, it’s not just about the money. Every friend and confidant we have asked for advice has said a resounding chorus of, “this wedding is about the two of you!” along with variations of “People should be focusing on how they can be there to support you. You should not be focusing on how you can accommodate others.” Partner and I expressed many concerns with postponing to my parents (we already made commitments! My parents aren’t considering anyone but my mom in this situation!) and the past two months have been emotional hell.

I am frustrated that my mom views my wedding as an Event In Her Life and not an opportunity to support her daughter, but also, this is the kind of person she is. I am frustrated that my parents didn’t consider my partner in all of this. I was also heartbroken about the possibility of having neither of my parents at my wedding (not that my dad would refuse to be there, but my mom would be unbearably upset if he went and she could not be there). My father, the fixer, hates seeing both his daughter and his wife heartbroken, and finally asked me again: if we agree to a date, and this date is the absolute line in the sand, and all the booked vendors have this date available, will you please consider it?

Partner and I asked our vendors about the new date and at first, we didn’t think availability would work. Plus, we really wanted to stand our ground because honestly, this is a pattern of us having to plan our lives around accommodating my mom. I told my dad no due to vendor availability and while he was sad, he understood. My mom, however, did not understand and expressed this to me through a barrage of “you don’t know how miserable I am” and “why can’t you do this for me.” The next day we heard back from more vendors and realized that logistically, we could make this work, so we gave in and officially postponed the date.

Partner was actually the one who convinced me in the end that maybe we really should postpone, and while we are sad, we are ultimately relieved. If we didn’t postpone and moved forward as normal, I likely would have had to sever all ties with my family and risk losing their financial support to avoid the emotional fallout. We made this choice to protect our peace. But I can’t help but feel like we were backed into a corner and pushed into accommodating my mom. It feels like a step back on the work I’ve done to set boundaries. I’m honestly worried my therapist is going to disapprove of us giving in to my parents like this (she has been a strong proponent of “don’t move your date to please your parents”).

At the end of the day, partner and I are happy with the choice we made, but how can we make sure that in the future, we’re not forced to make a sacrifice like this again?

Dutiful Daughter

Dear Dutiful Daughter,

Congratulations on your upcoming (eventual!) wedding and condolences on being in a situation where you both absolutely hate it and feel obligated to justify the sucky parts to others, including your therapist. Rock? Meet Hard Place.

You’ll notice that I kept your email subject line as the post title, with its question: Was it right?

If I were to say that your therapist and your friends made some excellent points, would it matter? You and your partner felt that it was the best option given the circumstances, you’re the ones who have to live with the decision, and you’ve already done the necessary scheduling adjustments. Here’s where I can maybe help:

First, you don’t need my permission, but you have it anyway: It’s okay to be angry and upset and not actually “happy with the decision.” You feel like you were backed into a corner because you were backed into a corner. You can make the compassionate, diplomatic choice to not make these feelings the center of how you communicate with your mom or how you and your partner communicate about your decision to postpone the wedding yet again. But I fail to see any upsides for you in pretending the feelings don’t exist or being mad at yourself for having them, and I fail to see how it’s your therapist’s place to approve or disapprove of you.

It’s okay to wish things were different. It’s okay to have compassion for your mom while she’s in crisis and hope for the best and also place her demands within the context of a lifetime of boundary-stomping behavior from her. It’s okay to grieve the experience you hoped you’d have. You’re not a bad person for wondering*, welp, what happens when the new wedding date is coming up and your mom insists on pushing it again or tries something else to wrest control of the event and make it about how you’re a bad daughter?

[*Is anyone reading this…not …wondering …that? My MIL almost didn’t make it to our wedding due to an untimely flare-up of a chronic illness, and it would have been so sad if she’d been absent, but one thing she did NOT do is demand that we move the whole shebang. My godfather had the same thing happen and unfortunately had to cancel his trip. I missed him, but nobody was mad at anybody about it. So I’m gonna remain forever skeptical of anybody who claims that your compliance with demands that make you worse off are the *only* way to make them better.]

Which leads me to the second way I might be able to help: You made a bargain in exchange for peace. It may have been a bad bargain. But you can’t get the cow back, so it’s time to plant these magic beans and grow as much peace as you possibly can under the circumstances. And I have two very concrete suggestions for where to start. They are:

  1. Ask for the promised money now.
  2. Stop planning your wedding, at least as far as your parents are concerned.

I’ll explain.

1. Ask your family for the promised wedding money *now.*

Goal: To remove concerns about money as a source of pressure on decisions about your wedding, and to regain a sense of agency and control over your financial future as a married couple.

If your parents are offering financial support for your wedding, they’ve promised to absolutely make it up to you for having to move the date, and one of your recurring fears is still that they’ll withdraw it at some point if they think you aren’t doing enough to accommodate your mom, what’s the worst that happens if you ask for that money now?

“Dad, we were able to rebook everything, the new total is $X. Are you still planning to contribute $Y, as we discussed? If so, are you able to advance us the funds now, so that it’s all settled and out of the way?” 

You and your partner have made a great effort to honor your parents’ wishes and set their minds at ease. Could they do something concrete to set your minds at ease by following through on what they’ve already promised?

This *shouldn’t* be a huge ask, right? As you point out, your families have made it clear that they want you to have a great party and be equipped to start your married life on the best possible footing. If postponing the wedding was in fact the right move, and things go according to plan, these contributions are a normal, expected, agreed-upon part of the plan. Your parents have both promised that this is so. But money is still a source of anxiety in your letter.

Because, of course it’s a source of anxiety! “When should the party be?” “It should happen when we’re reasonably sure Mom will be well enough to be there” is a far, far different calculus than “Should we buy a house, if yes, where/when/how much?” “Idk, it all depends on whether Mom feels up to attending this one party that we’ve already had to postpone multiple times and how Dad feels about that at the time, we can’t spend any money on anything just in case.”

Neither COVID-19 safety concerns nor your mom’s illness are anybody’s fault, but neither are they “just” about this one day on a calendar. If you and your fiancé know for sure that the wedding costs are completely squared away, it frees you to move ahead with the financial planning for all of those other parts of your married life, without it being contingent on how your mom is doing at any given time.

I feel strongly that removing pressure from a difficult situation rarely makes anything worse, which is why I think you should ask for the money and ask for it sooner rather than later. A “yes” will add greatly to your overall peace of mind and ability to plan your future on your terms, and a “no” will give you essential information for the next batch of decisions you’ll need to make.

First, even if your gut reaction is “nope nope nope, I can’t possibly ask for that right now,” that is information about whether you believe that your dad will keep his promise to cover the costs no matter what happens with your mom.

Second, if you ask, and your parents balk, that is potentially information about:

  • Whether they believe that the wedding will really happen as re-scheduled.
  • Whether they envision the money as a gift or as a bargaining chip in case they want you to move the date again.
  • If your mom is in the kind of crisis where “show up for one day in a nice outfit with six months to prepare” is out of reach for her, are they are still in a financial position to give you any money?

No judgment, especially about that last possibility! Just, if any of these things are true, I think that it’s essential that you find out now and adjust accordingly.

The goal is for you to reclaim financial security and a sense of agency with regard to your wedding.

The hope is that you’ll be able to have your wedding on the new date, at the budget and fanciness level you’ve decided upon, with the financial support your families have offered, with your mom back up to full “yeah” strength and able to attend.

The reality is that your best bet might be making the decision right now to pay 100% of the costs of your wedding yourselves, even if that means scaling back to a cheaper/smaller event and then treating any and all family money that comes your way as a nice surprise.

Listen, I despise wedding budget-shaming in both directions, I don’t think the performative cheapskates who brag about how they found a friendly spider to weave their wedding dress and fed their guests by foraging in restaurant dumpsters are morally superior to the caviar-and-champagne crowd. But sometimes the cheapest way to pay for things is with money. If postponing means buying you and your partner many more months of money stress, even if the promised cash eventually appears, that still might be Too Expensive. Your parents theoretically have the power to remove that specific stress from you right now, so will they or won’t they? You asked for advice about ensuring you aren’t “forced” to make sacrifices like this again, and I think getting very straightforward about the money piece is one of your best bets for being able to say, “I’m so sorry, but we’re not moving it again” if things don’t go according to plan.

“But it’s a gift, you’re not entitled to anything from them!”  Quite right! But your parents offered money for your wedding in the first place and offered subsequent reassurances that they would absolutely honor this commitment. You’re not some kind of brat for wanting to know that those offers are real before you write big checks.

2. Stop planning your wedding, as far as your parents are concerned. 

Goals: A) To free yourself as much as possible of having to weigh every single thing about your wedding against how your mom is doing or feeling at any given time. B) To find ways of maintaining boundaries with your mom with maximum care and gentleness for your mom, who didn’t ask for this crisis to be happening to her. C) To give yourself a break. You’ve been planning this wedding for three years. You planned the ever-loving shit out of it. It’s okay to be done for a good while.

In past wedding planning posts on the site, managing the expectations of all the people who are not members of the couple has been a recurring theme. Who decides what? Who needs to know, and when do they need to know it? What’s the difference between asking for input and communicating decisions that have already been made?

With the best of intentions, people want to head off future discomfort by talking everything through like adults, spelling out expectations from the start, and giving people plenty of reasons for why they are doing things this way and not that. Alas, some people are unwilling and/or incapable of engaging in good faith, and perceive “more discussion and more time to come to terms with decisions” as “more time to argue.” You mentioned in your letter that you don’t have an easy time being “real” with your mom, and that is unlikely to change now, so my suggestion is that you give yourself permission to not try so hard to include her. Why discuss a thing that you’re already pretty angry and sensitive about with a person who you already know tends to make things all about herself and who stresses you the entire fuck out, even when she is not in the midst of a crisis? Why buy yourself X more months of the same arguments you already had, and hated?

It is time to be as brief, boring, and breezy as possible. Think:

  • “Oh, Mom, thank you, but it’s all handled!”
  • “Mom, I’ve had all the wedding chat I can handle for two lifetimes. What else is new with you?” 
  • “Oh, we’ve already done the hard part,, we’re just excited to actually show up on the day at this point.” 
  • Think of it as a formula: “It’s going well” + “Thanks for asking” + “Howabout that subject change where you get to talk about you?”

If (when) this appears to backfire and you get accused of “shutting her out,” don’t take the bait! This is an area where it is okay to be honest and a little bit blunt.

  • “Ha, mom, we’ve been planning this wedding for three years. I know you are excited and want to help, but  I beg you, can we talk about books or current events? Watching anything good lately?” 
  • In case of a shame/apology spiral, interrupt it! “Mom, at this point we’re just relieved that we could move the date. Please, let’s not!” 
  • “Mom, you have one job right now, and that’s getting well. Don’t you dare stress yourself out over decisions that we made two years ago.” 

If she won’t take the subject change life-preserver you’re throwing, cut the conversation short and try again some other time.

If/when she makes specific suggestions you don’t like, don’t argue! (That’s also filed under “The Bait”)

  • “Interesting suggestion, we’ll think about it!” 
  • “Oh, Partner/Partner’s family is handling all of that, but I’ll mention it to them, thanks!” 

Promise nothing. Whatever fantasy either of you had about what a Mother-Daughter bonding experience this was supposed to be is long gone. Disengage.

When all else fails, time travel to a safe place that is all about her: The Past.

  • “Mom, I can’t believe I’ve never asked you this, but what was your favorite part of your own wedding?”
  • “Other brides all all say that it ends up being a blur. What are the best things you and Dad actually remember about your wedding?” 
  • “Did you and Dad, or you and Grandma & Grampa ever argue about wedding planning? What was the biggest disagreement about? What happened?”

Ultimately, you cannot hope to manage your mom’s emotions and reactions to anything involving your wedding. Mom is going to Mom! But what you can do is get very clear with yourself about the difference between “sharing a decision you and your partner have made about the wedding” and “asking others for their input” before you engage. If you know that your mom is likely to mistake the first thing for the second, maybe she doesn’t need real-time updates. Or any updates.

From there, I think it’s pretty much about contingency planning and reminding yourself & your partner that you are allowed to carry on, as planned, with or without your mom’s presence. You have done everything you possibly can to ensure that your mom can celebrate with you when the time comes, but you don’t actually need her in order to be married to each other. You are forming your own family unit where you prioritize each other, and this is where it starts. If moving ahead would really mean potentially cutting ties with that whole side of your family, that would suck so much, but that would also be a choice that they are forcing on you, not one that you invited by being inconsiderate or uncaring. Time to find a way to give yourselves credit for handling a hard thing in the best way you could at the time and figure out how to be a team during whatever comes next.

I don’t think it’s all going to be smooth sailing from here, but I hope your wedding happens according to plan and that it is a fun, joyful occasion. with everyone you most want to see.



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