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Hi Captain,
I need your help. I don’t know if I’m in a shitty relationship or if bad things just keep happening to us. I’ve been dating a guy for eight months. We fell in love very quickly and very intensely. The first period was very happy but I quickly felt very insecure and anxious about our relationship. I have generalised anxiety disorder and am often irrationally anxious. It has led to numerous situations where I was deeply worried about an aspect of our relationship, felt like we had tried as much as possible to fix it, and ended up trying to break up; however he would always convince me that we hadn’t really tried and that he wanted another chance to do better.
He is a rationalist who is deeply against living by social norms and just sees them as defaults, and is “non-default” about pretty much everything including work path, values etc., as well as lifestyle including cooking (lives off takeaway so as not to spend time grocery shopping and cooking), cleaning (does not have much of a regular cleaning habit – I broke glass in his kitchen a month ago and he said I shouldn’t have to clean it up and it’s still there), sleeping (he has no regular sleep schedule and sleeps when he wants to. The kind of work that he does is largely from home with long deadlines. He ships a prescription anti-narcolepsy from overseas which allows him to stay awake for long stretches on little sleep – although he plans on giving this up soon). He also takes party drugs and for a while, was taking quite high amounts of MDMA on a weekly basis, which pretty much wiped him out the day or two after. I have always been uncomfortable around drugs, although he did not really know the extent of my discomfort, and I can’t take them myself due to mental health. He dropped back to once a month after I expressed concerns about escalation and he acknowledges that he has some susceptibility to addiction, although he is not currently dependent.“
One serious issue we had was that he gave me an STI. He had rationalised that he had a very limited risk of having an STI so despite my repeated requests and despite being informed that a previous partner had been infected, did not get tested. I was furious at his intellectual arrogance and the danger he had put us both in. I lost a week of unpaid time off work and my mum had to nurse me through my allergic reaction to the treatment. I told him I wanted to break up, but we ended up supporting each other through the treatment and ultimately decided to get back together and work things out.
We have had some more rough patches lately. After agreeing that he would party on New Years, he ended up sleeping and feeling rotten through most of my birthday on New Years’ Day, which felt pretty lonely for me. He has been very stressed at work and had some issues with a very serious eye infection, which means that any positive changes around cooking/cleaning etc. have understandably stopped. I supported him through the eye infection by taking more time off work to wait at the eye hospital with him for many afternoons. We then went away camping with some of his friends, some friends-of-friends and a couple of my friends. Most of them did drugs, including one less experienced girl who wound up with drug-induced psychosis. It was a five-day process to get her help and it was extremely upsetting and worrying for everyone involved, and I once again could not work for the period. The experience reinforced my dislike of drugs and desire to not be around drugs, and as someone with mental health issues, I was angry and upset that the girl’s mental health was being blamed more than the illegal drugs she had taken. I told him that the drugs were too high a price of admission for me and packed my bags.
We have since traded emails in which he first said he did not understand why I left him and thought that I was being dishonest about drugs being the true reason. Through his logical arguments he has forced me to see that I was being irrational about my attitude to drugs and that it is merely a personal preference I have not to be around them, rather than any objective issue with the drugs themselves. I felt like the whole arguing process was unpleasant and cold and hated it. When he explained the break-up over drugs to his best friend, the friend replied by saying he should not to try and argue people out of their emotions and boundaries. My boyfriend doesn’t see the problem – he thinks if someone is objectively right, they’re right, and emotions that correspond with that are the issue of the emotional person. He is also extremely strong-willed and intellectually well-backed-up and is not used to being challenged emotionally, so I don’t think he realises how unpleasant it can be. I’ve explained this explicitly now and he found the concept very hard to relate to.
It’s really hard for me to check in with friends and family about this too. They all hear only have to hear me mention drugs to tell me I’ve made the right choice by leaving him. My family has had bad history with drugs and my sister, who used to take party drugs and was badly affected, told me “You’ve already been through a lifetime’s worth when it comes to drugs – you don’t need to go through any more”.
We’re now in a position where he thinks I’ve made a mistake with the breakup, and that I did not adequately justify my reasons for ending it. I ended up seeing it from his perspective and apologising for being irrational and hurtful. I love him and that we do have a lot of good things including a great amount of love, affection, good humour, and generally understanding. He says he loves me more than he loves anyone, that he needs me, that we are good for each other, that he wants to be the one for me, that he wants to make it all work. Our plans had included travelling and ultimately living together. I ended up feeling like maybe breaking up with him over the drugs had been an anxiety response rather than something I really wanted to do. But I’m worried about this narrative; as I type it I can see that it sounds really unhealthy (he would say that “sounds really unhealthy” is weak reasoning). I feel like I’ve paid a lot of costs over the STI, drugs etc., including lost work time, stress, and in particular with the STI pain and possibly ongoing health concerns. I can’t turn off the part of my brain that says that someone who loves me as much of as they say wouldn’t hurt me in these big and small ways. We’ve discussed this; he says he feels he treats me well; and I guess that I am now consigning a lot of my worries to pure anxiety, which makes me feel like I can’t trust my emotional reactions and that I should work on my anxiety and ultimately stay. I don’t know if that’s the right thing for me to do. I don’t know if we truly do have a problematic dynamic (despite having amazing things shared between us) or if it’s just anxiety at play. Have we just had bad luck at points? I can’t tell if this all feels so weird because his lifestyle and approach is so ‘non-default’ or because I am being manipulated. I don’t know if my anxiety is protecting me, or causing the problems. I so hope you and the Awkward Army can help with insight and advice.
Sincerely,
Worried about my worry but also my maybe(?!)-dodgy relationship
Dear Worried:
I’m worried, too. I’m worried about you and I think you need to be away from this guy for your own peace of mind and safety.
This guy completely lost me as a cool enough partner for you at “stopped you from cleaning and subsequently did not clean broken glass off his kitchen floor” because he has to prove he’s more rational than stupid societal expectations by literally walking around literal broken glass on his actual floor. For how long must this experiment go on before it’s his own (completely rational, separate from the oppression of society’s cruel and boring expectations) decision to clean up the glass?
And then I kept reading.
Let’s talk about the part where he “reasoned” himself around basic biology. If you’ve had partnered sex, and that partner has turned up with an STI, there is a non-zero chance that you also have an STI. Getting your ass to the clinic before you have sex with a new partner (or as soon as you find out) is your basic, human duty to others, and you frankly shouldn’t need “repeated requests” or any requests. STIs happen plenty without it being anyone’s fault or a reason to judge someone, but I judge him plenty for being so cavalier about a partner’s health when basically his arguments come down to “But I’m too lazy to actually find out.” And if he pressured you into having unprotected sex during this time? I will reach through through the internet with my mind and set him on actual fire. Being too lazy and self-involved to to to the clinic (or clean up pointy glass shards on the floor where you walk) and giving it a fancy title like “I’m just an extreme rationalist!” is a sign that this guy very, very far below you in basic adulting skills.
This part of your letter:
“We have since traded emails in which he first said he did not understand why I left him and thought that I was being dishonest about drugs being the true reason. Through his logical arguments he has forced me to see that I was being irrational about my attitude to drugs and that it is merely a personal preference I have not to be around them, rather than any objective issue with the drugs themselves. I felt like the whole arguing process was unpleasant and cold and hated it. When he explained the break-up over drugs to his best friend, the friend replied by saying he should not to try and argue people out of their emotions and boundaries. “
…makes me glad that the best friend spoke as they did, because they are 100% correct. So what if your decision was “irrational?” That doesn’t make it wrong. Breaking up is not a joint decision where one must prove one’s case beyond all doubt to the dumped party. You are allowed to give face-saving reasons. You are allowed to give no reasons beyond “I am breaking up with you.” When pushed on the issue of the drugs, you are allowed to say “You know what, you’re right, I was using that as a fig leaf. The issue isn’t so much drugs as it is you, and how I don’t want to be with you anymore. Farewell.” He could be the world’s most caring, drug free, glass-cleaning-up boyfriend and you would still get to leave him because your “irrational” heart says so. Wanting to leave is enough.
See also: “Think whatever you want to about why I’m leaving, goodbye.”

This movie is a) beautifully shot and b) a lifesaving case study of a predator at work on a vulnerable person.
You’ve tried to break it off numerous times, but you remain together because he bullies you and gaslights you into staying.
“We’ve discussed this; he says he feels he treats me well; and I guess that I am now consigning a lot of my worries to pure anxiety, which makes me feel like I can’t trust my emotional reactions and that I should work on my anxiety and ultimately stay. “
The problem in your relationship is that he’s a raging asshole, but he’s convinced you that it’s all in your head. His feelings that he treats you well don’t actually trump your desire to leave, or to protect your health from an untrustworthy sex partner, or your completely reasonable desire to not have to walk around broken glass (!) or stay away from people who use drugs if you know for sure that it makes you uncomfortable. He’s casting his feelings as logical “reasons”, and your very justified anger, dislike, and fear for your health and mistrust of him as illogical “anxiety” as a way to bully you and make you second guess yourself, because that’s the only way someone as awesome and compassionate as you will stay with his sorry ass. It’s a trap, where your sense of fairness and your own desire to be logical is used against you, because if he can talk long enough he can “win” the argument when you get exhausted. Trust: You can have an anxiety disorder AND still have real, genuine anxiety about the continued unsafety and hassle of making a life with this dude. The job of sorting out “real” anxiety vs. brainweasels falls to you and a trained therapist, not your shitty boyfriend.
Your family might be making drugs THE issue in an unfortunate way that plays into his hands – “They are just being judgmental and narrow-minded, etc.” – but they have many, many reasons to root for you to leave this guy so far in your dust that even your dust wants to shake the dust of this relationship from its little dust-bunny feet. Please forgive them for just wanting you clear of this entire thing, and for seizing upon the most obvious reason.
I’m sure this guy has good qualities and that you connected well in some ways; some kind of chemistry or desire would have to be present for you to put up with even a second of the rest. I don’t judge you for wanting really good sex or cool, unique conversations or that feeling of being deeply and intensely loved. I’m sure he sincerely wants to “do better” and believes that with another chance he will be able to do better, but you don’t have to give him infinite chances. If he’s such an amazing, deep, original person, he’ll find someone else after he’s had a chance to work on himself some. And you’ll find out that other dudes will be good in bed and smart and interesting and really dig your fine self. They will not carry this giant swamp of issues along with them. They will clean their apartments, and they will not bully you and make you feel crazy in order to keep you near them. Please believe me! Breakups, even of intense relationships are survivable by everyone. This is not your last, only chance at love or a serious relationship.
You say:
I can’t turn off the part of my brain that says that someone who loves me as much of as they say wouldn’t hurt me in these big and small ways.
Don’t turn it off! That part of your brain isn’t your illness talking, it’s your sanity. It’s your logic. You asked for my opinion. My opinion is RUN AWAY, RUN AWAY from this tedious motherfucker. Before you step on broken glass or get 9 more STIs or have to spend one more precious minute of your precious life arguing for the validity of your own opinions.
Unfortunately, there is no nice, easy, gentle way to get away from someone like this. You’ve tried normal breaking up like a normal person, and you always end up “logicked” back right where he wants you. So here are the steps for extracting yourself from someone who doesn’t want to let you go:
- Make a list of people you actually trust to love you and be nice to you. Friends who have no connection with boyfriend. Family. Team You. Get their emails & phone numbers handy. Maybe call one of them to come over and hang out with you while you do the next step or two.
- Find every item of his that could conceivably be in your house. Put it in a box and mail that shit to him. (Steps 2 and 3 can happen in any order, but should follow each other swiftly).
- Compose a message in your email program and save it as a draft. “(Boyfriend), I am ending our relationship. I need this to be a clean break, so I must ask you not to contact me again through any medium.” You can add something like “I wish you well” if you’re feeling it, but keep whatever you say short and make sure the request for no contact is explicit.
- Before you hit “send,” block him on every social media outlet and means of communication you share. After you hit “send,” block him on that email address, too. Congratulations, you are officially broken up now!
- No matter what he says or does, do not answer. You can’t have a tedious argument where he proves you are wrong to break up if you don’t talk to him or spend any time listening to him. You have plenty of evidence that he will not go quietly and may escalate attempts to contact you. If he comes to your house, don’t let him in, and if he won’t go away, call law enforcement. If he sends you letters or gifts, refuse delivery or put the stuff immediately in the dumpster. It isn’t your job to reassure him, help him “understand” or otherwise process your breakup, or deal with any of his feelings. You are broken up. He is responsible for his own emotional care. If Party Spock needs to cavort around with his broken glass collection feeling sad, let him do it on his own sweet time.
- Tell your friends & close people what’s going on. Tell them that you’ve tried to break off the relationship before, and that you might need some help now. Ask them for reassurances, compliments, hugs, breakfasts, lots of time together – whatever you need to feel loved and comforted, ask. They’ll give what they can.
- If you share mutual friends, and you start hearing troubling stuff from them, tell them, bluntly, “I ended my relationship with (Boyfriend) and need to cut off communications for a while so that we can have a truly clean break. Please don’t give him any contact info or news of me or pass on any messages from him.“
- If you’re not already doing this, seek treatment for your anxiety from a trained counseling pro and not your shithead ex boyfriend who was trying to use it as a chain to tether you to himself.
If you ignore him long enough, he will go away. And if you give it enough time, you will heal from this and move on.

The more anxious you are, the more likely you are to stay and “work through things.” This is not how good people get you to stay.
Worried Letter Writer, your instincts about what you deserve from a partner, about preserving your own safety, about whether being around drugs makes you happy, about whether you hate long bullying conversations where you are forced to justify every emotion, at being grossed out by someone’s living space are all perfectly on point. I’m not saying there is nothing wrong with how your brain works, but you can work on the anxiety disorder issue after you’ve dealt with the A Selfish Asshole Crawled Into My Life And Won’t Crawl Out Again problem. Do whatever you can to honor and thank that little voice that told you that something is not right here.
You’ve got some healing and recovery to do, and you may find books like The Wizard of Oz and Other Narcissists to be useful reading right now. “Narcissism” as a diagnosable disorder that your boyfriend has? Can’t tell you, wouldn’t wanna. This book as a primer on recognizing and abusive behaviors from people who are able to warp the reality around them and leave you constantly second-guessing yourself? Let’s say that someone who claims to honor rationality above all things but also thinks that the laws of science don’t apply to him, like, personally, is ticking off some ticky boxes for me and you may find some helpful stuff in here.
tl:dr Flee from this shitty dude as if your life depended on it. Your brain may be naturally anxious, but at least some of that is the good kind of anxiety that saved our ancestors from being eaten by bears.
