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Dear Captain Awkward,

I was estranged from my father, who emotionally abused me as a child, for nearly a decade. I was told he was dying of a terminal illness last year and his last wish was to talk to me. I figured, hey he’s a dying man and I’ve processed this in therapy. I can give him some closure. 

He ended up receiving a life-saving operation and has been given several more years. His recovery from the operation is grueling but he is stable and out of the hospital.

My problem is that I only came back into his life to say goodbye. I don’t want a relationship with him. I don’t want anything to do with him. I am occasionally re-traumatized by his behavior and even if I weren’t, I don’t like him. He’s still recovering and has a long road ahead. He needs support. I don’t want to even text him, let alone keep him company. 

I’m at a complete loss. It seems needlessly cruel to tell him the truth (“I only reached out because I thought you were dying so hmu when you’re at that point again”), but I don’t see an alternative. Ghosting just makes him pester my mom, sister, and husband. Low contact, even very low contact, is low-key triggering. I’m dealing with too much other shit to come up with a good script. Can you help?”

Hello!

If you feel like you must say something to your dad before doing whatever you were doing before to gain peace and distance from him, maybe try this:

“Dad, I am so relieved that your recent health scare wasn’t the end, and I appreciated the chance to give you and Mom some peace of mind during a difficult time. But that doesn’t mean our relationship has fundamentally changed. I wish you well, but I plan to go on keeping my distance now that we’ve had a chance to say our goodbyes.”

This doesn’t have to be a conversation or negotiation where he gets to have his say. You’re not asking permission, you are communicating a decision that you’ve made, so if it helps, put it in a greeting card and drop it in the mail. Done.

If (when) he tries other tactics, you can adapt that same script to set boundaries with your mom, sister, and husband: “I was grateful that I could grant Dad/you some peace of mind in a terrible moment, but that doesn’t mean anything has changed about the reasons we are no longer in touch. I wish him well, but for my own well-being, I plan to go on keeping my distance now that I’ve said my goodbyes.”

With these other family members, you might add something like “I realize that Dad is putting you in an uncomfortable spot, and I’m sorry about that, but I’m not going to change my mind. There is nothing you can do to fix what’s broken between us, and I am asking you directly to stop passing on messages and pressuring me to be in touch with him. As far as I’m concerned, we’ve said our goodbyes.”

These scripts are for you, to help you say what you need to say so that you can close the book for yourself. They aren’t about convincing anybody of the rightness of your decision or persuading anybody out of their hurt. There is no version of this or any script that your dad wants to hear or will accept, and he will likely take it out on anybody else in your family who will still take his calls. So once you deliver them, you’ll need to adopt or adapt all the boundary-maintenance measures that you already know how to do: Not responding to communications from or about your dad, changing the subject whenever he comes up, and cutting conversations short when you need to for your own peace of mind.

If your mom and sister are acting as his caregivers, consider that there are lots of ways to show up in their lives and be supportive of them without having to engage with your dad or spend every moment rehashing the latest details of his condition. Depending on your capacity, that could mean material support with meals, housekeeping, babysitting any niblings to give your sister a break, making sure mom and sister are taking good care of their own health, or arranging treats and distractions now and again. It could also mean words of encouragement, such as “I’m glad Dad has you in his corner, and you’re doing such a good job” as you change the subject to literally anything but That Fucking Guy. The same will be true when he eventually dies, since nobody has to feel any certain way about the un-dearly departed in order to keep hot coffee and casseroles flowing to the grieved and bereaved.

Estrangement is painful and lonely. There is always the “But what if the person DIES?” pressure from people who haven’t lived through what you’ve lived through, and people who don’t realize that nobody cuts off contact with a close family member as a passing whim, without exhausting every possibility for repairing the relationship. So whenever I hear of someone cutting ties permanently, I ask myself how bad would things have to get for me to never want to speak to someone again, and I generally try to assume that whatever happened to them was at least that bad. Letter Writer, now that you’ve lived through the “But what if he DIES?” scenario, and the answer is “He’s still exactly the same crappy person who caused me no end of grief.” If the pain of not having a dad anymore is still less than the pain of having to keep dealing with that specific, nightmare dad, then I believe you, and encourage you to keep doing what you need to do to protect yourself from abuse. You did a very kind, generous thing when you didn’t have to, and I hope you are giving yourself a lot of love and credit for that.

I’m wishing you peace and comfort in the days ahead.

Hello, I’m not sure how to start this off but here goes.

My wife of 20 years was caught sending nudes to an older man and I found out she had been riding around with him while I was at work. When I confronted her about everything she said they were only talking and it wasn’t sexual at all. But everything in me tells me otherwise. Also she has cheated in the past. Should I believe her?

Oof, hello, I’m sorry that we’re meeting under these circumstances and I hope you are doing okay.

I can’t confirm whether your wife’s ride-alongs with Pop-Pop involve the *full* Early Bird Special, and there is no universal “What counts as cheating?” standard that I could apply from this distance. But I’ll tell you what I observe and see where it takes us.

Your wife seems to be making the case that *nothing* counts as cheating or as being “sexual at all” until or unless the parties mash their genitals together and make them kiss. I tend to think of this as the N Minus 1 Gambit within the larger Cheater’s Defense, where as long as there is one forbidden thing that the relationship partner and potential affair partner are not doing (yet), then nothing they are doing could possibly be sketchy, and actually you’re the one who is out of line for even suggesting it. As the relationship progresses, and more and more formerly off-limits things happen between them, the value of N (for that final, off-limits act that would objectively constitute Actual Cheating) keeps growing progressively absurd, until you’re firmly in  “Well, it’s not like we fucked in front of everyone at the family reunion and sent the video to all of your LinkedIn connections, come on, be reasonable! We just did all the things I promised I wouldn’t do, one by one, until we ran out of Things. Quit overreacting just because I made you feel paranoid and crazy this whole time!”- territory.

You’ve found out that your wife is sending nudes to someone and hanging out with him behind your back in a way that feels “off” and reminds you of other times she has cheated on you. You could decide to believe her and ignore the whole thing unless it crosses a certain line, but you don’t have to solve for N (or accept the framing that it’s not cheating until she says it is) before you’re allowed to question your relationship and your happiness and security within it.

Please allow me to pose a series of questions that might help you think through what you want to happen next.

Are you happy with your wife, in general, or were you before you found out what’s happening? Can you be happy, knowing what you know now? When she denies cheating, but “everything in (you) tells (you) otherwise,” what is the cost of ignoring your own instincts? What happens to your peace of mind, to your sense of integrity?

In a perfect world, where all of this gets resolved to your satisfaction, what does that look like? When you ask her that question, what does she say? What happens if you let yourself be hurt and angry about this? “We’ve already had to work so hard to rebuild trust in our marriage, it’s both astounding and alarming that you’d push boundaries like this and put everything at risk, again.”

If it’s not cheating, then what is it? “Please help me understand. Why are you sending photos like that to another man? If it’s “not sexual at all” then what is it? Is it only him, or do you trade explicit photos with other friends? What do you enjoy about it? Do I need to be worried that you’ll cheat on me or leave me for someone else? Is there something you’re not getting from our relationship in terms of attention, or wanting to be seen, or even playing around with exhibitionism that we could work on together?” If there’s a reasonable explanation here, or something you’re missing, here’s her chance to offer it.

Do you trust that your wife is looking out for your well-being? Around this situation? In general? [Bonus Question: When’s the last time you got screened for sexually transmitted infections? STIs don’t discriminate and can happen to anyone without it necessarily being someone’s fault, but also, in my experience, people who aren’t careful with solemn vows and other people’s hearts aren’t always super careful about other stuff, either. It’s better to know than not know.]

When you talk to her about how this makes you feel, is she accountable and direct? Especially given the history of past cheating, does she acknowledge why finding out about the photos & secret hangouts might make you anxious and uncomfortable, and does she do her best to reassure you and make you feel safe?

If it turns out she is cheating, or it turns into cheating down the road, what do you want to do about it? If you both agree that whatever she’s doing doesn’t meet the threshold of cheating, are you allowed to say that you’re still not cool with what is happening and would like it to stop? Just because other people would be okay with what she’s doing doesn’t mean that you have to be okay with it.

If your wife won’t agree to curtail the photos and hangouts (or if she agrees but keeps going in secret)(or if she straight up tells you that she’d prefer to open up the relationship), what does that mean for you? Would you stay, regardless? Do you need to at least locate the nearest exit in case of emergency? What kind of support system do you have, including people who you can really talk to about what’s going on?

Even if your wife is telling you the truth (technically)(like, really, really technically)(hair-splittingly, rules-lawyeringly technically), it still might not be enough to build a happy future on, especially when she’s already broken your trust at least once. As boundaries go, “I only stick around in relationships where I don’t have to worry about being cheated on” isn’t a ridiculous one.

P.S. Pledge Drive Update: THANK YOU. Thank you to everyone who donated and thank you for all the kind messages. I have read them all.The last few weeks have been even more chaotic than I was anticipating when I put out the tip jar, due to Mr. Awkward having a sudden health scare that required a stay in the ICU. (Gory “Lithium toxicity? What the….?” details here, good “he’s out of the hospital and expected to fully recover” news here). Thanks to all of you, it was such a relief to be able to get back and forth from the hospital to be with him and summon food at weird hours without added stress. I’m especially relieved that I’m still on track for uterus-eviction next month as scheduled. If you can and want to chip in to the recovery fund/eventual comic staged reading of our itemized medical bills, you can sign up to be a monthly patron or use PayPal, Cash.me, and (new!) Ko-Fi. Thank you.

It is time for the recurring feature where I treat search terms that led people to the site as actual questions. No context, no backstory, all snap judgments.

First, a song:

All right, let’s do this.

1. What to tell your girlfriend when she ask you “the kind of relationship you want?”

What’s the worst thing that happens if you take this as an opportunity to dream about what kind of relationship you want and then tell the truth about those dreams?

What do you want? From your life? From this relationship?

In the best possible world, where you get everything you want, what does it look like?

If you ask her the same question, what does she have to say?

2. ” Intelligent way to answer what u looking for in dating site so that you fuck her?”

Uh, there is no sentence string known to humankind that guarantees someone will want to have sex with you, but you’ll probably have the best luck if you keep it simple: “I’m looking for fun, friendly casual sex partners.”

3. “How to ask a friend if i can use her summer home without her in it.”

A BOLD MOVE! Maybe try “Do you ever rent the place out? I’m looking for a getaway spot for [A family gathering][A romantic weekend away][Some alone-time to recharge] around [dates]. My budget is roughly $_____.”

If you sense any hesitation from this friend, back off and find somewhere else to stay.

If the friend says yes, you will obviously leave the place in immaculate condition.

4. “What does it mean when your boyfriend introduces you as a friend.”

My first instinct is, he’s introducing you to people who don’t know him well or don’t know he’s in a romantic relationship. There can be lots of reasons for that, ranging from “He’s not out yet, or out to these people” to “Surprise! He’s married with an entire family” so a good follow-up question when you’re alone is, “Is there a reason you introduced me to so-and-so as your friend and not your partner?” How he answers this will give you lots of information.

Speaking of…

5. “My divorced boyfriend want to keep me a secret.”

Got you something.

Questions that immediately pop to mind:

Are you sure he is actually divorced? (In your shoes, I would literally check court records.)

Are you sure that he’s actually your boyfriend? Is this an “I’d like to keep my options open” kinda deal?

Is there some obvious reason, as in, is he your boss or coworker just trying to keep things profesh at the office? Are you dating someone who isn’t out about their sexuality or identity?

He may have his reasons, but you don’t have to help him prop up a lie. “Let’s break up. Come find me whenever you work things out so this doesn’t have to be a secret.”

6. “My husband lets his family walk all over him.”

You cannot fix your husband’s family, and you cannot fix your husband, so let’s talk about what you can actually do about it:

1) You can encourage your husband to seek therapy and tools for learning to set boundaries and unlearning some things about the way he was raised.

2) You can become the Emperor of Boundaries where your own well-being (and the well-being of any children you have) is concerned. He might not be able to say no to his family, but you can say no to them and to him about things that adversely affect your life. “No, your parents /your deadbeat sibling cannot live with us.” “No, they cannot ruin every single vacation and holiday celebration.” “No, your mom cannot be in the delivery room when I give birth.” “No, I’m not eating at their house anymore since every time I do they put mushrooms in the food.” “No, they can’t verbally abuse me or our kids and expect us to put up with it.” “No vaccines, no masks? Then no visiting the baby, period.”

See also: “I realize that your family can be very overbearing, but the way you’re pressuring me to go along with my own mistreatment right now is a you-and-me problem and I need you to stop.” “Difficult Family Member is going to get upset no matter what you do. If you keep [ditching our plans][giving them money we can’t afford][giving into their demands][Not standing up for yourself/me/our kids] every time they demand it, kindly remember that I am also your family and I will also be upset with you.”

The saying no isn’t about getting him to change or getting them to change. It’s about protecting your peace by refusing to get caught up in their antics. For better or worse, your husband is in charge of how he handles his relationship with his family, but you have all the say in how he handles his relationship with you.

This question is incredibly, incredibly common here and in other advice forums around the internet, and it is a brutal dynamic to live with, to the point where “Hrmmm, I love this person a lot but they can’t seem to say no to anybody but me” is probably something to screen for *early* in the relationship.

7. “How to quit on being a godparent.” and 8. “How to quit bridesmaid.”

Ideally, before agreeing to be a godparent to a child or stand up in someone’s wedding (or accept a freelance assignment, or agree to some complicated favor), try this:

“I’m so honored, thank you! But, before I commit, can you tell me what that entails?”

ASSUME NOTHING. Ask the person to spell out what they envision your role to be. “Come to the baptism, say some words, give good presents on gifting occasions, be a trusted adult who also loves my kid” is different from “Be at every single event my child ever does and promise to raise them if something happens to me.” “Wear a nice dress on the day and be my friend during wedding planning” (s/o to Commander Logic) and “Plan, pay for, and attend nine separate events on three continents where you will both set up and tear down the decorations and also change your body so you ‘match’ the other attendants” are not even in the same universe.

Based on their reply, if you have a strong, immediate “Yes, I’d love to!” or “Oh, that all sounds amazing, but I know I don’t have the funds/bandwidth/time/resources/planning ability to do it right, so can I RSVP now as an enthusiastic guest?”

If you’re on the fence at all (and/or if you’re a recovering over-scheduler), try: “Thanks for spelling it out, that all sounds exciting! When do you need an answer? I need some alone time with my calendar and bank account before I commit.” Then take a day or so and actually do the math. If the answer is no, try “I am so happy for you and excited to celebrate with you, but I can’t commit to the ______ role. I wanted to let you know ASAP so you can make another plan.” The person might get upset or try to negotiate, and that’s understandable. Ride it out. You know your own limits.

Unfortunately for these querents, it’s too late. I’m going to pull from past advice about breakups, quitting jobs, and moving away, and suggest that you think of it not as a negotiation, request, or exploration of reasons and past events. Rather, you are communicating a decision you have already made so the other person can make a new plan for the future. Give as much lead time as you can, and then be clear, direct, and firm.

Scriptwise: “Friendname, I am so happy for you and so honored that you asked me to be a [role], but I’ve realized I cannot follow through with what you need. I’m so sorry to upset all of your plans at this stage, but I’m going to withdraw as [role] now, before I get even more over my head, and while there is still time for you to make a Plan B.”

I’m assuming here that there is no glaring conflict where “Uh, you know why” would suffice. (I think there is an inbox question where “The groom hit on me, repeatedly. Fuck no I’m not being in your wedding anymore, are you even serious right now?” would be entirely appropriate.)

Brace yourself for some “But why?” and gnashing of feelings. If the person is reasonable, and you think there is a “why” they will accept? Tell them. “I just really and truly cannot afford either the money or the time commitment.” “I’m pregnant and your wedding is the baby’s due date.” “I can tell that ‘godparent’ means something totally different to you than it does to me, and I’m so sorry I didn’t ask you to clarify it from the start.” “I got into graduate school. In France. So I’m not going to be around to actually help you with any of this.”

Sometimes there is no “why” they will accept, and that’s when “I’m truly sorry, but I know this is the right decision for me” is all you can do. “I know you are disappointed, and again, I’m truly sorry, but my answer isn’t going to change.”

It sucks to feel like you’re letting a loved one down when they you to be a part of a very important occasion, but I promise, it sucks WAY LESS to say no up front than it does to agree because you’re afraid of disappointing them and have to drop out later.

9. Many, many variations on “how do I have sex as a fat person/with a fat person” that range from the earnest to pornographic

Start with Hanne Blank’s book, Big, Big Love.

If images and sexy videos are your thing, seek out media made by and starring fat performers. It’s out there, and you clearly have working search engine, so godspeed!

10. “Can I block clingy ex even though I promised to be friends.”

Yes. It’s not mandatory to stay friends with former partners. Even if they want it. Even if you promised. You get to change your mind!

If you want, right before you block, send one message along the lines of “I know I promised we’d stay friends, but I’ve realized that I need a clean break and I would like you to stop contacting me. I wish you well.”

Then comes the hard part. Do not reply to any further communications from them. If they ping you 37 times and you answer the 38th ping, you’ve shown them that it takes 38 pings to get your attention, so next time they’ll play it safe and go for 39. Every time you interact with them after you asked them to stop, you’re prolonging the detachment process. Once you block, let yourself be done! You don’t need to explain why, you don’t need to “work on” a relationship that you’ve ended or help someone get over you. If your ex deputizes mutual friends or people in your life to guilt you into resuming contact (a common tactic to get around blocks), tell those people “Ex and I aren’t in touch anymore, at my request, so I need you to stop passing messages and info back and forth.”

11. Captain Awkward Firthing

Originally mentioned in A Shy Guy Caught My Eye. Refers to the practice of staring balefully at someone you have a crush on instead of actually talking to them, and letting the feelings build up until they erupt out of you in a terrifying volcano of thwarted desire a là Colin Firth as Mr. Darcy in the 1995 Pride & Prejudice adaptation.

Mr. Firth has since gone on record that he’d prefer we call this “Darcying.”

As you were.

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.