You Need Help: How Can I Plan for a Bad Breakup?


I’m in my most volatile long term relationship to date. Things are frequently and currently great, but she is a troubled creature who isn’t willing to look inwards. This has led to some horrible situations, and surely will again. For my own sake, I always keep one eye on the door, but I’m in uncharted territory here. My inquiry in case it becomes necessary to break up: I would like advice/stories about how to disentangle oneself logistically from a long term relationship that ends badly (which it absolutely would, if it goes there). We don’t live together, but I keep a lot of my stuff at her house and we have a ton of plans months in advance. How have other people navigated bad breakups with logistical hurdles?


This is one of those instances where I think there’s a lot of blanket advice out there and it’s important to understand that your situation is uniquely yours and there are a lot of nuances to consider. Sometimes people respond to questions about fractured or toxic relationships with the blanket advice: BREAK UP. Even though you’re couching some of the language by saying things like “if it goes there,” it does sound to me like you’ve already reached the conclusion that you should break up but just naturally have some doubts and reservations. If you’re indeed having doubts, I would definitely nudge you in that direction based on the minimal but telling details you’ve provided. If you’re thinking this hard about breaking up and mentally planning for the fallout, I think you should break up.

But the question isn’t really should I break up? but rather how can I break up? And that’s where things get tricky!

“Planned breakups” aren’t always a good thing. Sometimes they’re a result of someone just being too scared to break up even when they know it’s what they want to do. It’s unfair to the other person to be harboring these feelings instead of just communicating and ending the relationship and can often lead to resentment, cheating, etc. To me though, that’s not what’s happening here. Some breakups do have to have some advanced planning because they involve tricky logistics or toxic or abusive situations where leaving isn’t as easy as just having a conversation and walking out the door. Again, there aren’t a ton of details in your letter, but I’ll take you at your word when you say the relationship is volatile and there have been “horrible situations” with this other person (though I do want to push back on the words “troubled creature” a bit just because it sort of takes away her humanity a bit, and I think moving through this breakup with empathy will be important for your overall sense of well being! I promise I have YOU in mind with this gentle pushback). Since I don’t have all the details as to your relationship and any harm that has been done, I am going to give advice that kind of assumes near-worst case scenarios, so feel free to take or leave aspects of this!

Don’t worry too much about the plans you have months from now. If they’re things like trips or vacations, it’s possible after the breakup that you’ll be able to get refunds or travel credits, take the trips with someone else, or possibly lose some money that has already been spent. It sounds like your financial and living situations are not tied together, so that’s at least two major things you don’t have to worry about as much. Have you spoken at all with a therapist? Therapists can be really helpful in constructing a plan to breakup and helping you figure out what to say and do. If therapy is not accessible to you, have you opened up to any friends about this? I would of course stick to friends who primarily or exclusively have a relationship with you and not your girlfriend, which I know can be hard in a long term relationship, but hopefully you have folks who are squarely in your corner.

In fact, I would make a plan to stay with one of those friends in the immediate aftermath of the breakup, if you can. Again, it helps that you don’t live together, but if situations tend to get volatile, it might be best if you have somewhere to stay for a bit that she doesn’t have access to. Protect yourself digitally too; if you have each other’s locations, make sure to turn that off and change any passwords she might have access to. Gradually move some of the items that are at her house that are most important to you back to your place, but you might also have to accept that you will have to lose some things in the breakup. Try to get the things you value most out of there.

Maybe this is just because I’m a writer, but I find it helpful to journal through the process of a breakup. It’ll keep you grounded, remind you you’re doing the right thing, and be like a record of what you actually feel in case your ex attempts to gaslight or emotionally manipulate you down the road.

I know you said you’d also like to hear stories, so I’ll leave you with some personal anecdotes about how my last breakup unfolded on a logistics level as well as things I wish I’d done differently. We lived together for about four years, and toward the end of that, we were no longer together, so the first mistake I made was not immediately moving out after the breakup. I ended up losing some money to the breakup, too, as there were pieces of my furniture I couldn’t logistically move on the timeframe my ex wanted me to, so I had to pay to have them disposed of. I also lost a cat in this breakup because I foolishly made assumptions instead of getting any arrangements in writing pertaining to who would get the cat, and the cat was then used against me for emotional manipulation (at least from my perspective) and I ended up having to just make the choice to let her take the cat instead of trying to fight. To be honest, by then, I was tired of fighting. I was ready to move on, even if she wasn’t. At a certain point, you do have to realize that the breakup is a huge loss, and sometimes that doesn’t even just mean losing a person but other parts of your life, too. There isn’t really an easy or clean-cut way to disentangle two lives after a long term relationship, especially when it ends badly (as mine did as well). I’ve almost never heard of a breakup that didn’t come with some sort of literal financial cost in addition to all the emotional costs. Do everything you can to protect yourself and keep the things you care about but also know you might have to give some things up.

Ask! For! Help! Breakups can be so isolating, but it is important to surround yourself with people who are going to support you in this decision and be there for you. Ending a long term relationship often means losing the person you relied on the most (even in bad relationships), so make sure you’re leaning on other people instead of falling back into old patterns.

You can chime in with your advice in the comments and submit your own questions any time.

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 837 articles for us.


  1. This is all good advice. I would add:

    1) Make the break as quick and clean as possible. So very often breakups get worse when they happen in stages, or with repeated meetings afterwards, and this is exponentially true of bad breakups. Much better to have it be a shock—which it often feels like, even when you plan and initiate it—and then let the two of you work through your feelings with people who are not each other.

    Cancel or change all plans you have together afterward—in my experience, any friends involved will understand. In your case, I sense some real concern about the things you have at her place, which often wind up being the source of drama even when the breakup is amicable and adult. Kayla is right that you should get the stuff important to you out yourself beforehand or accept that it will be destroyed/you’ll never see it again. You might consider asking a friend to pick up any remaining stuff from your ex and deliver it to back to you in order to avoid repeated contact if you think that strategy might dial down the drama. But I would avoid meeting up again for a pickup—that can go very wrong.

    2) If possible, have the actual breakup conversation as a one-on-one conversation in neutral and public place, like a park or a restaurant. Some place where you’ll have reasonable privacy but there are people around. Avoid your homes/locations with loaded associations/family holiday gatherings/Pride celebrations/other people’s weddings etc. If you can’t, and the breakup winds up happening at a less-than-ideal time and place, just know that you are not alone in having that miserable experience.

    Good luck! You sound like you have good instincts and know your heart and mind.

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