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Dear Captain Awkward,

My male friend is engaged to a (female) Darth Vader. She (the Darth) literally sucks all of the fun out of everything. She is ALWAYS embroiled in drama, whether that be with my friend (he/him), at her workplace, with her family, with her neighbors … literally, with EVERYBODY. They have been together for four years, they just moved in together last month, and their wedding is scheduled for next year.

My predicament: my social group (co-ed) is very close. The women of the group (of which I am one of them) also do side-hangs that are female-only. The men do too, but that’s less about having a mens-only space vs choosing to do an activity that none of the women are interested in, vs our hangs (female-only) that are purely out of wanting a female-only space. These are usually camping weekends, pool/beach days, occasional happy hours. Maybe 3x a year.

Anyways, we (the women) all cannot stand Darth. (The men can’t either, but they tolerate her better since she usually wants to hang onto us at events) She drains our energy, she’s ALWAYS complaining about our friend (who has been in the group for 10+ years, vs her four), she doesn’t respect our boundaries about topics we’re willing to talk about (such as our friend – we’ve tried to make her stop), we catch her in constant lies/flip-flops that are baffling (who wanted to get married, how the proposal went, who wanted to move in first, whether they were moving into a new house or she was moving in with him, whether her mom likes him, whether her friends like him, etc), she has a terrible habit of getting very drunk and cornering one person to unload all her anguish onto (at a WEDDING she once cornered the GROOM to tell him how she couldn’t wait to be pregnant and that she and our friend would have to quit our friend group and find Parent Friends to hang out with) … it’s just a lot. So: we would like to exclude Darth from our female-only hangs. Is that okay? I think it would really hurt her feelings (but EVERYTHING hurts her feelings) and I think it would bother my friend, but we did do a group check-in a while ago to express our groups concerns about Darth to him and he said he was happy and thanked us for our concern but wants to keep dating her.

I hate that I feel icky about excluding her, but I frankly can’t stand her either.

Thanks for any advice you can give.

Hello! Thank you for this question about Geek Social Fallacies gone wild. 

As a start, I think you should go ahead and plan the next all-woman friend hang without this person you don’t like. You’re allowed to just do it! 

For best results:

• Pick something low-key that doesn’t need a long lead time. (Fewer moving parts, less planning back-and-forth, and much less time for someone to spill the beans. Keep it simple!)
• Don’t use the normal, All-Group channels that are visible to either Darth, your friend, and the menfolk. Call or text the women directly to invite them. 
• Actively take the lead in planning, and emphasize the “I” over the “We” in any written invitations and logistical stuff you send out. “I’d like to see some of my favorite ladies for [activity] on [date], can you join me?”  (This will be important later.) 
• Do not put Darth’s name or anything about her in writing. If necessary, use the phone or face-to-face conversations to tell invitees you’re experimenting with planning “more intimate” events, so you’d appreciate it if this specific event remained invite-only and off of social media. I predict most of your compatriots will pick up what you’re putting down fairly immediately, but if you need to be more specific, try “I want to try hanging out with just us, no Darth this time, but I don’t want it to be A Whole Thing, so use a little discretion, thanks.”  
• Organize/attend the actual thing and have a great time! 
• While you’re all together,  resist the temptation to bash Darth in absentia, even though I realize that you are only human and there is a lot of material/catharsis. You can’t control what people will do or say, but still, I beg you, try your best to redirect the conversation so this lady doesn’t ruin a party she isn’t even at. “”If we talk about Darth the whole time, it kind of ruins the part where she’s not here.”  “I don’t think she’s technically a Candyman, but shhhhhhhhh, let’s not risk summoning her by accident!” “Someday I’m probably going to have to look Friend and Darth in the eye and say that we didn’t plan this whole thing just to exclude and bash her, so help me out!” 

If everything goes smoothly, congratulations, you’ve enjoyed a Darth-free friend hang and established a new normal where including a person you loathe is not mandatory for seeing friends you like. By just going ahead and planning it, you will have pre-empted a massive group melt-down over whether this is even possible. In future, other women in the group can either piggy-back on your success and enjoy more Darth-free hangs, or they can default back to the old way out of guilt and obligation or the off-chance one of them actually likes her. Either way, you can keep planning Darth-free events when it’s your turn to organize stuff, because you don’t actually need permission or consensus! (Consider that it is actually way less mean to host a party for just the people you like without trying to convince a whole group to share your exact feelings or create social bylaws about who is allowed to exclude whom.)

Remember when I said that owning all of this as your decision would be important later? When you’re hosting an event, you get to make the guest list, and if someone tries to argue with you about that, you can say, my party, my rules, next time, when you organize something, invite whomever you like! This goes for the other women in the group AND the men. “You’re free to invite her on your hobby weekends if you care so much!” “She doesn’t like hobby!” “Okay then! Since it’s not your problem, then you’ll forgive me if I find my own solutions.” “It’s only a couple of times a year, why make a big deal about it?” “Exactly, it’s only a couple of times a year, so why is she making such a big deal about it? I don’t recall marrying anybody!” Keep using ‘I’ language and embrace being The Difficult One for a change. The second you try to invoke the Reasonable “We,”  you’re fucked, because then it IS actually a “We all got together and decided we don’t like you ” Group Grievance, also known as The Drama-Monger’s Banquet.

Now, let’s be honest, I don’t think that you are going to be able to avoid any and all awkward confrontations about this forever. Especially as their wedding approaches, everything will probably escalate as Seating Chart Theatre gets underway, so there’s that to look forward to. Eventually, Darth is going to find out that she’s been excluded from stuff she used to be grudgingly included in, and she’s going to be loud and weird about it. She might be loud and weird directly at you, but my prediction is that she’s going to cause enough stink that her betrothed and the other menfolk in the group are going to try to outsource all of that to you and the other women to handle like you’ve been handling it up until now… by ruining every single all-girl vacation for the last four years for the concept of group harmony. (Seems harmonious!)

Again, speaking for yourself and only yourself is going to come in handy. I didn’t say it would be easy, comfortable, or smooth, but it will be handy. 

If Darth comes direct? Be direct in return. “Darthname, I can see you are upset, but I’m not going to argue with you about this. I invited the exact people I felt like hanging out with that day, and I’m allowed to make plans without you and without consulting you.”

Say your thing and leave/mute the conversation as soon as you can. Don’t text back and forth (or at all), don’t invest time into indulging her grievance, and don’t fake-reassure her. I feel like it is a HUGE part of socialization of women and girls, especially white, neurotypical women and girls, that Everyone Must Pretend To Like Each Other All The Time, and that The World Will End if someone you actively dislike gets the accurate impression that you do not in fact adore them. I do not know who this is supposed to be FOR. It sucks to be pressured into acting like you like people you don’t. It super sucks to sense you are disliked but then have people fake-reassure you that they like you and then pull the rug out when the pressure to fake-like you gets to be so much and they explode, and now it’s not just that they don’t like you, it’s that they think they have to have an airtight list of reasons that you objectively suck because “eh, so-and-so kinda irks me” isn’t enough to justify all the faking. Whatever the fakers are worried will happen if they drop the act, the reality is almost always worse, for everyone. 

Which, this is where are are now. It doesn’t feel good to reject someone to their face, but you’ve tried faking this shit for FOUR YEARS. It sucks that your friend’s fiancée is under the impression that she inherited this close-knit knitting circle, but you have also told your actual friend straight up that you don’t like her and he’s been like “Okay, but I love her” and continued inflicting her on everyone. So it’s decision time. Are you going to fake-invite this lady you hate to everything you do forever, even though she does not even actually seem to want to be your friend (so much as to be the Bull in the China Shop Of Your Social Occasions) or are you going to risk some truthful bad feels and maybe set yourself free in the process?

She’s going to be shitty no matter what you do, so you might as well do at least some of what you want. And look, even if you liked her, dating your friend doesn’t automagically make someone your bestie or give her administrator privileges over who you hang out with and when. So if Darth keeps pushing you, or your friend gets manipulated into pushing you on her behalf, some things are going to come to a head, and one of those things might well be, “Friend, I know she’s very important to you, and I’ve bent over backwards to include her in stuff for your sake, but it’s time to accept that not everyone is destined to be close. There’s a difference between being pleasant and kind and looking for the best in her because she’s your partner, and inviting her on every girl’s trip I take for the rest of time, when you’re not even there to be a buffer. She and I are simply not compatible enough for that, so  I’m going to need you/everyone to drop this expectation and this subject.”

Will it harm your friendship to set a boundary? Hard to say. If you have this argument out loud, you may end up seeing this friend less, both because he wants to be loyal to Darth and because she insists on it. If she’s actually abusive vs. just unpleasant, she might use this as an excuse to isolate him from you and others, but you can’t prevent that by faking it or putting up with bad behavior forever. Abusers will find a way. Anticipating their every move at the expense of your own well-being is not your job! 

Again, I think the key throughout is to own it as your personal decision/need/quirk, and not try to invoke or convince anybody else to feel the same way as you. If your 95 Theses About Why The Love Of His Life Actually Sucks didn’t get through to your friend, you can freely embrace euphemisms from now on. “Oh, X and I  just rub each other the wrong way.” “Oh, X and I just didn’t gel like everyone hoped we would, it happens.” “Oh, you know what, after four years I think it’s clear that X and I will just enjoy each other more if we stop trying so hard to make fetch happen.” “Yeah, sometimes it just doesn’t work out, not everyone is meant to be close friends.”  “What matters is that *you* love her! I’m just along for the ‘I want my friend to be happy’ ride.” 

Gonna leave everyone with four wishes:

1. May this lady make or seek out her own friends who actually like her.
2. May your friend reckon with his beloved’s bad behavior instead of outsourcing it to all of you to keep the peace and pretend things are fine, and may he figure some things out before the wedding. 
3. May you release yourself from the pretense that this lady’s behavior and feelings are your fault or your problem.
4. May your future vacations include only people you like.  

Hi Captain,

I’m just looking for advice on a situation that is starting to drive me crazy – my mum won’t accept anything I (she/her) tell her as being true or correct unless it has been “fact checked” by my brother or dad.

Over the last year or so I’ve noticed it becoming a lot more frequent that whenever I say things to her I get some variation of ‘that doesn’t sound right/ that can’t be right/ are you sure? You should go and check with/ ask dad or brother about that.’ Whatever the issue is we are discussing, my dad or brother will invariably go through the same checking process I have already done and come to the same conclusion as me, but because the answer now comes from them she will accept it.

For example – I am currently in the process of moving into a different apartment that will mean finances are tighter for me. My mum insisted I should check to see if I am eligible for state benefits as I am in a low income job. I told her that I had already checked and wasn’t eligible but she didn’t believe me. So last week when I visited them I filled out the eligibility check again to physically show her so she would stop nagging me about it, but even doing it in front of her she still didn’t believe me. She kept insisting I was wrong as my brother gets benefits even though he earns more than me (he has kids, i do not) and that I must have filled out the checking form incorrectly. She then got my dad to fill it out for me and it was only when he did it and still got the same answer that she very reluctantly accepted that I had been right. I tried to talk to her and tell her that I felt annoyed and hurt that she hadn’t believed me the first time but she became extremely defensive and doubled down on the ‘but you might have put the wrong answers on the checking form’ and then said “but don’t you think it’s always better to get everything checked by one of the boys anyway? I do.”
I don’t. I’m an adult in my 30s, I have been living independently for several years and I resent constantly being second guessed on everything I say and treated like I can’t be trusted to know how to do things or fix things on my own without the help of a male family member.

This is also causing issues with my brother who is currently living with them. He is 3 years older than me and he has made it clear he thinks I’m stupid and incompetent because I am a female. He uses misogynistic language and talks down to me all the time, and whenever I go home to visit he spends the whole day constantly interrupting me to mansplain whatever I am talking about. Its got to the point where on my last few visits it made me so annoyed I had to threaten to leave and go home if he didn’t stop interrupting and talking over me. Instead of apologising he just laughed in my face, and my mum told me off for being angry instead of acknowledging why I was getting angry and standing up for me.

All this to say, I feel that my mum is subconsciously enabling his behaviour by constantly referring to him or my dad to check whatever I have said, and this is reinforcing the idea in his head that I can’t be trusted to know things or do things without his input. It’s got to the point where I don’t enjoy visiting them anymore because each visit invariably erupts into constant arguments when she refuses to take me at my word and brother piles in to talk over me, talk down to me and mansplain everything I say.

For some background I feel really sorry for my mum. When she was younger she wanted to pursue a career in science but she wasn’t allowed to study science subjects at school. She was forced into taking domestic subjects like cooking, cleaning and sewing because she is female. She has told me she is resentful that my gran didn’t stand up for her and push for the school to let her do the subjects she wanted. I feel like part of this whole issue is caused by her projecting her own insecurities and lack of confidence on me because she has never been empowered to stand up for herself and back her own abilities.

How do I communicate to my mum that I need her to knock off the ‘fact checking,’ take things I say to her at face value and trust my autonomy to know and do things by myself?

Many Thanks,

Annoyed Daughter

Dear Annoyed Daughter,

When you tell your mother something about your life, and she insists on having one of the men in your family ‘fact-check’ you, including the one who is sexist and actively mean to you, and said men participate in that fact-checking, and it proves you right, I’m curious.

What happens next? She “accepts” it. So, does she say, “Oh, okay, sorry to interrupt, please continue telling me about that” or “Wow, what a tough situation” or “Is there any way we can help?” [Is there something in particular you wish she would do or say?]

Or is the matter somehow “closed” once everyone does their little dance because it’s “not worth” “the hassle”/”the drama” of continuing to discuss whatever it is especially now that you’re so “angry”? (This is my guess.)

I ask because I’ve seen this pattern many times before:

1. Child sets a boundary or simply relates a true experience, fact, decision, or aspect of their own life. “I go by [Name} and my pronouns are _____.” “I am planning a small, intimate wedding, so I will not be inviting this list of 200 people you handed me.” “Please don’t stop by my place unannounced, call first.” “”I don’t eat mushrooms.” “I’m moving apartments, so money is tight right now.” “No, I checked, and unfortunately I don’t qualify for benefits.”
2. Parent compares the child’s statements against the imagined child who lives in their heads and the parent’s fantasy about what “should” be happening in the world. 
3. Parent attempts a power play, making it clear they prefer their imagined version of their child and how the world works over reality, and set the child up to have to prove whatever it is before they can receive [Acknowledgement][Care][Accommodation][Respect][Support][Basic human decency][Not being poisoned by mushrooms]. Letter Writer, your problems literally do not exist until they are validated by one of the men in your family, and the only possible help* or care your mom can offer are her own incorrect, outdated, and unhelpful fantasies. (*Not that you were even necessarily asking for help!)
4. The child dutifully attempts to prove whatever it is, which is easy, both because the child is the expert on their own experiences, because the facts are on the child’s side. But instead of clearing up the problem, things get even worse when the parent doubles down.
5.  The parent blames the child for not matching the parent’s fantasy expectations and punishes the child for reacting with (reasonable) hurt or anger. The parent punishes the child for not submitting to the parent’s perceived authority. “I’m your mother, I only want what’s best for you!” “We’re a family, so you should ______.”  The parent scapegoats the child, and calls in other family members for backup to help pressure the child into accepting the unacceptable behavior. For instance, when your shitty brother spends your visits criticizing you,  “…my mum told me off for being angry instead of acknowledging why I was getting angry and standing up for me.” 

So far you’ve tried identifying why this is happening (maybe your mom’s experiences of sexism when she was young?)  and you’ve also tried telling her outright that this bothers you and asking her to stop.

It didn’t stop. And I don’t really have magic persuasive script where you and your mom talk this through like adults and she sees how she’s hurting you and changes her ways. Your mom is interacting with a fantasy version of you in a fantasy world (the one where she is a caring and supportive mom and where her son isn’t a sexist dipshit), and then treating the real, actual you like dirt. I don’t think that can be fixed with persuasion that doesn’t have some action behind it.

So here are my suggestions:

Take steps to conserve your energy and peace. For instance, you don’t enjoy visits to your family right now. Do you have people in your life who you actually enjoy visiting? Prioritize visiting them, and strongly consider that staying home where nobody treats you like crap is superior to having to show up to a command performance of filial piety where everybody treats you like crap.

When you do visit your folks, plan shorter ones, try to plan things where you and one parent alternate doing stuff outside the house (away from brother), and have an exit strategy for extracting yourself early (your own transport, a reliable friend who will come get you) when it all goes pear-shaped. When you can’t politely persuade someone to stop being a jerk to you, there is power in being able to say, “Welp, nice seeing everyone” and putting on your shoes.

Your family treats everything in your life like it needs fact-checking and second-guessing. Do you have people in your life who respond appropriately and supportively to your life news? (“I’m moving apartments, so money’s a bit tight lately.” “Oh, bummer! Moving is the worst!” “Oh no! Once you’re settled, want to plan some free or inexpensive hangouts while things catch up?”) Prioritize spending time with supportive people who don’t try to force you to justify your very existence, and when you need acknowledgement and support, skip your family and go straight to people you can actually count on.

I’m not saying “cut off your family forever” or “never speak to them again.” Nor am I suggesting delivering some ultimatum in the hopes that it will teach a lesson. (It won’t.) I am saying, give yourself permission to stop making effort within these relationships for at least a few months. Save the money you’d spend traveling, concentrate on moving into your new place and getting settled, and give yourself a break from the effort, expense, and mental load of keeping in close touch with a parent who routinely blows off everything you tell her about your life, a passive parent who enables it, and your terrible brother.

When you do see or otherwise interact with your family, I suggest you skip the fact-checking performance and apply a time-saving translator to your mom’s deflections. When you tell your mom about your life, and she reflexively calls in the mansplainers, try ***internally*** translating her reaction as: “I don’t have to care”:

• “I don’t have to care, until a man says that your situation is actually real.”
• “Oh, wait, it’s real? Huh. Well, I’m mad that I’m being forced to care, and it’s your fault, because you didn’t take all the (unsolicited)(wrong) advice that I tried to give you instead of caring.” (Can’t lie, your mom has big “Unemployed? That’s easy, just show up in person at companies you want to work for and knock on the door until someone lets you in, that’s what we all did back when university cost $10!” energy.
• “I don’t have to care, and frankly I find your poor attitude about how much I don’t care and how much I deputize your brother to abuse you incessantly quite appalling.”

***Internally = quietly, inside your head. Do not ever have an out loud argument with your mom about whether she cares about you, under any circumstances, there is no good outcome there. Whether your mom cares about you and how much is not the point. I’m sure she does care about you. The point is, she is not responding to the things you tell her with care, so, once you acknowledge that to yourself, how much work do you feel like doing to “prove” the basic circumstances of your life?

Your next step is to skip the fact-checking performance altogether. Stop playing the game. You don’t actually need anything from her (or your dad, or your brother) for your life to be what it is, so why waste the effort fighting about stuff that’s totally irrelevant because you’re going to do what’s best for you anyway? Meet her derailment with the same amount of deflection, and make it very boring for her to keep trying this with you. Scripts:

• “Oh, hahaha, I’m all set with research. Anyway, what’s for dinner?”
• “Oh, I wasn’t asking you for advice, I was just telling you my plans. Did you move the jade tree? It looks so nice over there.”
• “Interesting advice, I’ll consider it. Is that a new scarf?” (You will consider it, and discard it. This is not a lie and it does sometimes get people to STFU imagining they’ve won the point.)
• “Yep, I’m sure. Anyway…” 
• “Okay.”
• “Huh.”
• “Wow.”
• “Hahaha, no.”
• “Not relevant.” 
• “Why are you being so weird about this?” 
• “You’re being weird about this again.”
• :Stony, awkward silence followed by a subject change: Let her talk herself out! Then change the subject, or return to the actual topic as if she didn’t do this.

Honestly, you don’t have to be deferential here. The goal is to make it powerfully, consistently, amazingly unfulfilling for your mom to keep doing this. “Ha, Mom, did you know they make calculator apps for phones and you can just use your finger to press the buttons? No penis necessary!”  “Mom, I know you love the thing where Dad and Brother re-run all my numbers, come up with the exact same thing I did, and we pretend that’s relevant to anything, but I’d prefer not to.”  She’s going to blame you for being uncooperative and angry before the visit is over anyway, no matter how patient and deferential you are, so why not earn it for once? If your mom has never seen how truly angry this deflection and minimization game makes you, if you’ve never raised your voice and been like “MOM, STOP. I DON’T NEED FACT-CHECKING, I NEED YOU TO MAKE SOME VAGUE SYMPATHETIC NOISE THAT INDICATES THAT YOU HEARD WHAT I ACTUALLY SAID. DAD, PUT THE ABACUS AWAY. I’M NOT DOING THIS,” and then left the conversation, maybe it’s time. “Your brother is just being himself, no need for you to be so angry!” “ACTUALLY I AM EXTREMELY ANGRY, THANK YOU FOR NOTICING.”

Your mom is the chief architect of this dynamic, but your dad and your brother both suck in their unique ways. You’re allowed to say, “Yo! Dad! The last 500 times Mom made you ‘double-check’ something I told her, what happened?” “What’s that again? I was right? Well, I’m going to be right this time, too, and on the off chance I’m not right I’m still going to go with my original plan, so, howabout we just skip it!”  “Hey, Dad, you’re free to fill out pointless government forms I’ve already filled out, but it’s not going to change my decisions, so, why are you doing this?” 

Your mom doesn’t have to “accept” the things in your life for them to be real. So skip the part where you try to spin the straw into gold. Shrug with your whole body and stop playing your part in these little skits about how the daughter who handles her own life is secretly the family loser.

Next, I mentioned this before, but stop threatening to leave when your brother is a jerk to you and when you’ve tried to shut down Fact Checking Theater and your mom refuses. Don’t threaten, just actually go away to somewhere they can’t be mean to you.

You could say, before the next visit, “I’m excited to see you, Mom and Dad, but just so you know, if brother does [x specific behavior] again, I’m leaving,” but you could also decide at any time when you’re there that this visit sucks and you’re not having fun and it’s time to go. Polite advance warning won’t actually do anything about the behavior, it will probably make your brother behave even worse the next time you see each other to try to get you to leave (or prove that you’re afraid to), and you’ll still be The Rude/Unreasonable one when the story is told later no matter how it goes down. The worst part is you are probably going to feel like the rude and unreasonable one because you’ve been conditioned to feel that way and because it doesn’t feel good to be pushed to the point that “Fuck this. Bye!” is the least worst option.

Important: It only works if you actually leave. Threatening, mentioning, hinting, etc. will NOT work. You have to actually get up and go, and probably actually silence your phone and have a cooling-off period to wait out the pressure and verbal abuse where they try to make you the problem, and wait a little while longer before you make any new plans to visit. So if you go this route, make a plan before the trip about what circumstances would make you leave, how you’d leave, line up a supportive friend to call if you need  help leaving or support once you’ve left. The first time you get up and walk out of a visit to your parents’ place will be the hardest time. It will suck, but you have to know: It is survivable, and with time and consistency it can get easier, partly because you get more experienced and partly because sometimes people learn that they have to treat you a certain way if they want to see you, and they do adapt somewhat. (Eventually.)(Somewhat.) If they don’t adapt, it doesn’t make leaving a worse option than showing up to be picked on again and again by people who assume they know more about your life than you do.

Once again, my inbox has been filling up with variations of the following story:

Dear Captain Awkward, my relationship hit a MAJOR rough patch, and even though [I][[We]My Partner] have tried very hard to fix what was wrong, it’s still not fixed, and I am still not happy. How do I know when it’s time to pull the plug? Is it even fair to leave now, after everyone has worked so hard to fix it by [working on themselves][going to therapy/rehab]? Am I allowed to leave even if I suspect/fear the other person doesn’t really have anyone else they could count on? What if I never feel this way about anybody again? What if I never feel “in love with” my person ever again? Is it too late?

If this describes where you’re at, I want to give you a small project, a variation of the assignment for the person who fears they married the wrong person or the one for when both halves of a couple wrote in.

1. See if you can buy yourself some time away from your partner & other obligations to be alone with your thoughts. Can you visit a supportive, warm, encouraging friend or family member or do a little solo getaway for a few days?
2. Grab a notebook and an incognito browser window and start working through the logistics of dividing up households, money, and co-parenting, stuff. Convert “Should I stay or should I go” to “If I go, how should I do that?” For example:
   1. Are there safety concerns? I’m going to write the rest of this list as if there are not, but if there are, now is the time to get some expert advice and make a safety plan.
   2. Where would you want to live and work? Imagine your ideal living space, where you’ve picked out everything and it’s all set up just for you.
   3. If you have kids, what kind of co-parenting & custody arrangement would you want?
   4. If you don’t have children, and you are a person who can get pregnant, do you a way to control your pregnancy risks? If you have the ability to get your partner pregnant,  can you take extra precautions against accidental pregnancy?
   5. What should happen to the money and stuff? Consider: What’s best for you? What’s truly fair? What would set up everybody in the best possible financial shape for the future? What could everybody live with, short-term?
   6. What resources do you have – family, friends, work, financial, educational, health – that you could call upon for help if you really needed them?
   7. Are there people you haven’t talked to in a while who would be happy to hear from you, just because? Or that you’d be happy to talk to, just because? Make that list, too.
   8. Are there hobbies, interests, and social spaces that you really miss? What would it take to reconnect with them again, even in small ways?
   9. If you’ve been in more of a caretaker role in relation to your partner, what care of yourself have you been postponing or neglecting? Do you need to go to the dentist, get a haircut, replace that worn or broken item?
   10. If you’re legally married or partnered, what are your legal options like where you live? Remember, consulting a divorce lawyer does not necessarily mean hiring a lawyer or following through with legal separation. Right now, it just means gaining a better understanding of your options so that you can make informed choices.
   11. Overall, what does the best possible breakup look like, where everybody is left in the best possible position to thrive?
   12. What are some possible worst case scenarios? How likely are those? If one of them happens, what would you do about it?
   13. Apply the Sheelzebub Principle: If things stayed exactly as they are now and were unlikely to change, how much longer would you want to stay? Another year? 5 years? Ten?
   14. Imagine that you’ve already broken up and have started doing the hard stuff. What does your life look like in a year? Five years? 10?
   15. Now shrink back to the next 3-6 months. Are there any big decisions or purchases that would be very different if there was a pretty good chance you won’t stay together? Do you need to redirect some money/energy/effort now while you’re still working things out in your own mind?
   16. Free space for jotting down feelings and ideas that come to you while you’re working through the questions. Especially watch for attempts to prioritize your partner and make your future housing/finance/care decisions subject to theirs. You don’t have to pre-solve all of someone’s problems before you’re allowed to leave them! Make a note of them when they arise and keep going with your own planning.

I know that digging into these details before you’ve even decided to end things seems like skipping a lot of steps, but that’s entirely on purpose. You may use this information to proceed with breaking up, or you may never use any of it. That is also on purpose! I’m not always good with identifying and applying feelings myself, which is why I’m suggesting an end run around them, on purpose. Don’t try to solve what you feel. Try to imagine what you would do if the thing you fear happens, and then check in with feelings. Do any of these action items and daydreams of the future make you feel good things? Excitement? Relief? Flickers here and there inside all of the fear, grief, and anger?

When you’ve been in a relationship for a long time, and when the relationship or a partner has been in some sort of crisis for a long time, framing “how you are doing” in terms of “How The Relationship is doing” becomes an ingrained habit. “If we can just hold out until [graduation][rehab][The Holidays][That big trip we already bought tickets for], then things will be okay.”  “If partner would just _______, then things would be okay.” “If I could just make myself _____, then things would be okay.”  “It’s not a good time, I’ll worry about that once [Partner][The Relationship] is okay.”

After a while, it can start to seem like everything good in your life is out there somewhere past “Fix The Relationship,” and you can’t have any of it until you beat that level. And you can’t beat that level. So you can’t have the other good things. Unless, this time you beat that level. Except, you can’t. But maybe this time you will? If left unchecked, the inertia just spreads and spreads to almost every aspect of life.

But just for this weekend away, for this one little moment, I want to break you out of that loop. If the relationship doesn’t ever get fixed, if it’s not fixable, how will you get what you need and want from your life? Can you, even briefly, imagine a world where you are safe, loved, fed, taking care of yourself and those dear to you and being taken care of by your community, working on your dreams and aspirations, and enjoying your life again, that does not depend on solving the equation of this one person? What else could you do with all the time you spend trying to fix everything?

Ultimately, only you can decide when and whether it’s time to leave a relationship. If you decide to go, I want you to leave with a plan for how you’ll take care of yourself. If you decide to stay and keep working on things, I want you to relax a little bit because you already know that if the thing you fear happens, you will ultimately be okay. Either way, maybe you can start reconnecting with some of the people and things you love now, and start taking better care of yourself now, and maybe it will be easier to be generous and hopeful inside your relationship knowing that you don’t *have to* stay together forever if it’s truly not working. I’m sending you all and hope for safe landings.

Dear Captain Awkward,

I (27, she/her) have a sister (28, she/her) who is in a very different financial situation than me. She has more savings, thanks to our parents having a history of giving her financial help and leaving me to fend for myself (quick example, they put her through college for 8 years and refused to contribute anything to my studies). She also has a higher income than I do, and she has a husband who also has a significant income. I am aro-ace and without any sort of life partner.

Now she bought her dream house and because she didn’t want to use her savings and commit to a longterm loan, my parents gave her a large sum of money so she could buy the property. And, because my parents have always preached about wanting to keep things even between the two of us, they have now promised to give me the same amount of money once I find a house to buy. Sounds nice, right?

Except…my parents don’t actually keep things even between us, ever, and they have a long history of going back on (small and big) promises. A couple of years ago, they bought a small flat, which they first promised to gift to my sister. She wasn’t interested in the flat, because her husband’s parents were letting them live rent-free in a bigger flat of theirs. So then they promised the flat to me. Except when I asked to follow through on that promise, they backed out, saying they didn’t want to give anything big to me as long as they couldn’t give the same to my sister. They wanted to give something to both of us at the same time. Then they promised to let me rent the flat at a lower rate ‘for as long as I wanted to’. Even though I urged them to put it in writing (even inviting them to put an end-date on this, so all of us would have a set date to keep in mind), they declined to. A couple of months later they started kicking up a fuss about this deal and started ‘hinting’ I should move out of the flat.

So now they’ve given my sister a big amount of money and — in spite of all of their earlier ideals about giving us a big financial gift at the same time, so as to be sure no one would be left out — they are back to the vague promises to me of giving me my due someday. I am currently not in a situation where I can afford to buy property, even with the sum they would be giving me, so I can’t take them up on this promise right away. So I want them to put it in writing so that I can rest assured that this money will still be on the table once I can/need to use it. Which they are refusing to do.

Obviously, I am afraid that if I want to buy something in a couple of years’ time, they will have gone back on their promise by then. On top of that, there is always a risk that one or both of them will die soon, in which case I would be dependent on my sister to first let me have the share that is due to me before splitting the rest of the inheritance equally amongst the both of us. To be clear: I also do not trust my sister to be fair about this.

Therefore, I have tried to convince my parents to put this promised money in writing, and they are refusing to do so. My sister has emphasized how much she trusts me and how much we trust each other, and I don’t know how to come out and say that I don’t trust her, or them for that matter, without burning important bridges.

How can I convince them to put any of this on paper?

Kind regards,
Anxious about Future Finances

Dear Anxious:

Your sister is clearly the favorite child, your parents are obviously jerks about this, and I do not think you can ever count on money from them. Ever. Every time they want to give your sister money, they will. Every time they don’t want to give you money, they won’t. They’ll use “fairness” as a made-up excuse (classifying monetary gifts to your sister as “help” and the bare minimum of rent control for you as “freeloading”), and they have flat out said they won’t sign anything about their intentions. I mean, they are making your entire point for you: If they sign something, it will be harder to break their promises next time, and they’d prefer to keep their promise-breaking options open!

So here is what I think you can do: 

Stay in the low-rent flat for as long as it is financially convenient for you, moving is expensive and hard so don’t do it if you don’t absolutely have to. Do not respond to hints about leaving. If they want you to go? Make them come out and ask you to go.

In the meantime, use the savings on rent to sock as much money as you can into a down-payment on future housing, and moving costs, as well as an emergency fund in case they do ask you to leave or sell the place out from under you. Pay your bills on time and pay attention to your credit history and score. Plus, if you can afford and have access to therapy, “my parents keep making and breaking promises to me but then go all out for my sister” is a good topic to take there. They probably don’t see their behavior as rewarding your sister for following the kind of conventional life they approve of and as punishing you for not doing the same thing, but it’s incredibly obvious that she is the golden child and you’re the afterthought here. 

For now, drop the subject of money with them. As long as you’re not imminently buying a house, they can keep brushing it off with “when the time comes,” so why not let them for now? When you are ready to buy property of your own in the future, don’t loop your parents in to the process. Select properties and apply for a mortgage based on what you want and can afford for yourself without their help. [Depending on where you live there are many programs to help first-time home buyers with down payments and closing costs, so do your research]. 

When you’ve found a home you like and can afford on your own, THEN let your parents know that you’re getting ready to buy and ask: Are they able to offer you the support they promised in the past? If they say yes, great! You can ease some of the stress and financial burden with whatever they give you. If they start in with “But what about your sister?” you can say, “Er, not sure what she has to do with me buying my first house, but, are you still able to supply the $X you’ve mentioned in the past? It will really help me calculate how much house I can afford if I know the exact number.” 

Start out cordially, treat them as if you expect them to follow through with what they promised, and make them do the actual work of letting you down. [Which they most likely will.] Even if they agree, in principle, be prepared for them to find fault with every listing you show them, and watch out when they try to attach a lot of strings. I anticipate lectures about how “entitled” you are and that’s why it’s actually your fault they won’t give you money that they outright promised to give you someday. Your sister needs money for literally anything? They’re delighted to help, they’ll even buy a whole apartment that she doesn’t want! You mention the subject of money? FAUX PAS. Do your best to laugh at the obvious hypocrisy and brush it off, and remember that money from them isn’t real until it is in your bank account. Do not enter into any agreements that depend on money from them coming through, don’t give them the power to eff you over.

If you think that your sister will advocate for you, send her on a mission with a script like “Parents, you gave me [MANY MONIES, LARGE NUMBER] to help me pursue my studies, buy a home ,and stay out of debt, and you’ve always promised the same to LW when it was her turn. I know how important fairness is to you, so I’m sure you’ll do the right thing here!” They don’t care about you, but they actually seem to give a shit what she thinks of them, so use that without shame or apology if she’ll agree to actually help. 

If nothing works, when things inevitably deteriorate, you can say, “Okay, thanks for telling me so I can make a good decision for myself,” and buy your home without a single penny from them. It’s completely up to you whether they are ever allowed to set foot in it. 

I don’t think it was silly of you to ask for promises in writing, since your parents kept falling all over themselves about how they value “fairness.” By asking outright, either you get the promise and the cash, or you get concrete information that the money was always a lie or a tool of manipulation. But now you know, and probably the healthiest thing you can do for yourself is to let go of expectations about it. They should just do what they promised, true! But that “should” is a trap as long as you invest your time and effort in people who (literally!) are not investing in you.

I wish I had some secret script for you that would get a different result, but you have a ton of evidence that this is how your parents are. They will make any excuse to provide for your sister and don’t feel bound by promises they make to you. It is ultimately their money to do with as they wish, and this is the kind of relationship they are choosing to have with you. You can’t change them or their minds, but you can choose not to base important decisions on winning their approval or waiting for them to deliver on empty promises. From where I see it, the whole situation is neither fair nor fixable. Maybe that information can at least be freeing, in some way?

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