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I have a roommate I allowed to sublet with me. I have allowed their SO to move in with them. Currently I'm not receiving rent from the roommate, and that's an entirely different problem of my own creation, because I had them leave their previous job for an opportunity we ended up getting left hanging on. But I felt the lack of rent paying was important to bring up to explain the circumstances here.

I have been covering the rent, and I told them to not stress out over it. I did not tell them it was okay to not pay rent, but rather to not stress if they were short. We have been waiting on roommate to get work from the person we invested in. SO has gotten 3 jobs and quit every one of them in less than a week during this time. They never tell me when they quit a job, only when SO gets a new one.

SO gets envious of my employees, because I pay other people to do work that SO feels capable of doing, but never actually does. I've given SO chances to work for me in the past to earn cash, and jobs have been unfinished. This has lead to tension in the household, where I never see roommate unless its with his SO. I feel taken advantage of by the SO, and not the roommate.

How do I talk to the roommate about this? I have anxiety when I think about handling the situation. I'm unhappy that SO has left multiple jobs without making enough money to pay me back. SO has told me in the past when I asked for some rent money, that I told them not to worry about it. This is where I feel SO is being manipulative.

SO has admitted to me in the past that they will cause a scene to get what they want in situations. I feel that they are doing this to me. My anxiety is causing me to not know how to handle this discussion.

I have only about a month or two more of this before I have to ask you guys about kicking them out while retaining friendship. But for now, how do I discuss this problem with roommate without SO freaking out? When I have tried to handle things in the past, it has resulted in SO throwing a tantrum and not acting like an adult. This triggers my anxiety.

Edit from comments

TLDR:

  1. I have two tenants, we shall call them "roommate" and "SO"
  2. Roommate is unemployed due to a fault of both of ours, so I am covering rent until the job opportunity we pursued together pulls through for them
  3. Roommate is kind and respective, and I allowed their SO to move in
  4. SO started off respectful, but is now rude, demanding, and makes me uncomfortable in my own home
  5. SO is also unemployed, and when I gave SO opportunities to work for me in the past, SO never completed their work
  6. I would like to approach roommate and find a way to settle the issue (be it by reinstating rent, asking SO to move out, having SO fix their attitude issues, or another resolution) before I damage our friendship beyond repair
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    When you say "discuss this problem with roommate" - what problem is that? You've so interlaced the rent issue with the rest of the question that it's difficult to see where the two separate. Are you looking to address the issue of the SO's job failures? Their envy about your employees? Does the SO owe you money other than the rent you've already told them "don't stress out over it"?
    – Catija
    Apr 22 '18 at 18:54
  • The problem is that SO is treating me poorly, despite not making an effort to keep a job long enough to pay me. I feel that I shouldn't be treated like I am
    – Kristoff
    Apr 22 '18 at 19:22
  • But what, concretely, does "treating me poorly" mean to you? Where are your expectations differing from the SO's actions? Please don't take this to mean I'm arguing with you. I'm attempting to understand the situation more clearly. :)
    – Catija
    Apr 22 '18 at 19:24
  • An example from the other day. The AC was set to 80, which is really high and not normal. I asked them "Hey, are you guys changing the thermostat? it was set to 80" and the SO comes at me with "Why are you assuming it was us? Next time you should ask us instead of accusing us".
    – Kristoff
    Apr 22 '18 at 19:45
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    What do you want to change after the discussion ? That the SO stop acting like that ? Reading as I read, that sounds like quite a dream. The only thing I can see is clearly remember firmly that they're at your place and if they can't show proper respect, they can look somewhere else.
    – Walfrat
    Apr 23 '18 at 7:14
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Lazy people often take advantage of the good nature of hard-working people. From the details you give it sounds like you initially had some confidence in your original roommate working and contributing, and that their reason for having no income is not their fault. However the SO seems to be work-shy, and assuming you are right to retain confidence in your roommate, the SO is perhaps taking advantage not only of you but also of your roommate.

For this reason, even though they are a unit, try and view the situation with these two people separately before you try and tackle them together.

Your anxiety seems to be over your original agreement with the roommate. You did make vague promises to them about not having to pay rent. But the current situation is very different from when you said that. There are now two of them, and even if you didn't specify a time limit on this rent-free period, it cannot be expected to go on forever and must be "reasonable". You would be right to talk to your roommate and agree a reasonable time frame on all of this - a deadline on them gaining work from the "investment" you spoke of, or elsewhere, and beginning to pay rent.

The "don't worry about it" arrangement did not really apply to the SO as they were not around when you first sublet. So you are completely in your right to have a conversation about their contribution to rent.

I would suggest going to the roommate individually to speak about this all, but try to keep the two issues separate. First look to consolidate and update the original agreement between the two of you. Perhaps say:

We need to talk about the rent situation. Obviously in the beginning I was okay for you to hold off contributing until work came in, but that hasn't worked out the way we intended so we need to have a revised agreement. It isn't reasonable for me to pay your rent for you, so we need to set an end date for the current arrangement. [state whatever you think is reasonable] I think that is a reasonable time for you to find employment and begin contributing.

If roommate tries to turn the subject to the SO getting work, just say:

We'll discuss them in a moment - this is regarding my original agreement with you before they came here.

Make sure you reach an agreement that is clear, not vague like it was before. Set amounts for rent, and a definite date that this must begin.

Then move onto the SO:

Regarding [SO] - there is no reason they shouldn't already be paying rent. I expect them to start paying immediately [or whatever nearer deadline you think is reasonable]

If she tries to invoke the "don't worry about it" agreement, just state:

That was an agreement I had with you alone, and in very different circumstances. Your situation has changed, there are two of you and it is unreasonable for neither of you to contribute.

Regarding your goal of retaining friendship with your roommate - I often mention the Karpman Drama Triangle in my answers as I find it fascinating and helps us get a grip on why situations like this happen. If you get any three people in a drama, two people often form a unit against the third. It does not mean you are the "bad guy", even if they project the blame onto you. Love is blind, and your roommate may initially see you as the "persecutor" in this drama. But someone who quits jobs for fun is definitely no "rescuer" - they would be completely incapable of looking after the roommate in any real-world situation. It is only your good nature that has allowed them to survive with the SO being so feckless. Once you force reality upon them, I think the roommate will see the SO for what they really are and it likely will not last.

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The long and the short of this is that your friend, though your own statement, is having difficulty paying rent but this is through your joint "investment"- irrespective of what this is, the important thing is them earning money.

Tackle this one point at a time:-

Though you've stated that it's not really a problem, there needs to be an agreed on timescale going on here, so have you got an idea on when exactly this investment is going to lead to something? Is the housemate actively working at all? Do they have any income whatsoever? If this is something you can agree on, it will make things smoother.

The SO is the real problem here- she wasn't present when you and your housemate spoke about rent, employment and the "no big issue" rent being mentioned. You agreed for her to move in, but was anything ever said about her and the rent?

Important bearing here is where you stand in terms of legality and the place itself- is it yours? Co-rented with the housemate? Is there any documentation at all? Has anyone signed anything? If it's just you and the housemate, then she'll need something in writing if she wants to take this situation further than "hissy fit".

Firstly, I would speak to the housemate, clear up the employment and rent issues- agree on something solid and work off that foundation.

Next, get the SO involved- state that although you were happy for the housemate to be here, it was with an understanding and agreement between the two of you regarding employment and rent; she was allowed to be here as well- but this is under the understanding that she contributes towards the rent and that there's to be no interference regarding your housemate and work.

A clear divide is awkward to work through the realities of but needs to be made- this SO seems to be manipulative and not afraid to make it clear she'll throw her toys out of the pram if she's not getting her way. It would be best to speak to the housemate first and build off them as a start before moving onto her- assuming that you get on well enough it may be worth approaching the topic of her before speaking with her, just make him aware of why you feel it's necessary and explain your reasons behind it- this way if she tries to spark off the situation, you'll have a safety net of sorts as he'll already know what this was about.

If it helps at all, going back to the legal standing and documentation- depending on what your footing is like and if she makes it clear that things aren't going to work out- you'll have to use this card. Unless she's an approved tenant on paperwork- she has no right to be there. Even if she is, depending on if this place is yours or not, give her notice to leave.

I understand this isn't ideal but as much as you might want everyone to get along nicely, if she isn't going to meet you halfway and uses the housemate as a weapon against you, it may not be possible to go any other way.

Ultimately, the arrangement was working well enough between you and the housemate, but the SO has complicated matters. It's not necessary to be hostile with her, but depending on how she's wanting to let this play out, after all is said, you may want to be sure you've explored some options.

Hitting the title question, though:

Speak to him. He's not going to know or understand any of this without you putting your point over, so do so. Unless you're going as far as recording her saying things to you, one would hope that your word of mouth is sufficient enough to get the point to him that things need to change. She wasn't part of your understanding regarding rent, her mentioning or being involved in work matters between you isn't appreciated and go from there.

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