Dear Captain,

I am in a tough place with a long time close friend. My partner and I are currently roommates with this friend. We have been all living together for a little over a year in a shared apartment (everyone’s name is on the lease).

Friend is a wonderful, kind, smart person, but he’s been in a bad spot for the past 4 years and seems to constantly be in a very slow decline. We are all in our early to mid 30’s college educated professionals, but roommate has not worked consistently in years and nearly at all in 3. He’s been fired from multiple positions in a row. He has not ever had a relationship though he claims to want one. He is not in school, volunteering, or otherwise doing anything to move forward in his life. He’s clearly struggling, but while he’s openly discussed that he’s had issues with anxiety and depression, and is on medication/sees someone about this, he otherwise attempts to act like everything is completely fine. He spends large amounts of money he doesn’t have on his hobbies, hangs around the house constantly in his pjs, sleeps very late/stays up all night, and really only goes out if its to do something “fun” or if it’s related to his hobby, and is often not conscientious to the household as a whole.

Other notes on our and roommates situation

– He does pay his portion of rent. See next point for more on that

– He is not in a position to not work. He is being given cash by family members to float expenses but there is also large amounts of debt on multiple credit cards. His family is not able to do this indefinitely and it’s clear that his finances are a house of cards that is going to collapse.

– Partner and I do not want to live with roommate after our lease is up. We have a few more months on the lease, and for us all to find housing we need to inform him now. We do not plan to kick him out. Current plan is to offer to either turn the apartment over to him and move out, or take over the lease if he’d like to move. However I doubt he will get it together enough to make a plan to move (see above stagnation), and there is a high likelihood landlord would not allow him to remain in the apartment without us (see lack of income), so us moving “kicks him out” by default

– His alternative free housing option would be with a family member. This is roommate’s last choice option and he would hate it. It is not unsafe or abusive, but it would not be what he wants

– He does not have a drug or alcohol problem ( I am 99.9% sure of this)

– We knew he was having issues when we got a place together. At the time we thought it was more situational and less due to his actions/ lack of action, and that living with people who cared about him and were also productive adults would be helpful to roommate. My partner and I both agree now moving in together was a bad call on our parts

– We live in an area where finding employment in things like retail/ serving jobs/ temping etc is not difficult. He seems to think this type of hourly work is beneath him.

– It’s clear he views himself as a part of me and my partner’s family unit and seems to think he will remain as part of our household indefinitely.

At this point myself, my partner and all our mutual friends are extremely concerned about him. It’s become clear that his situation is a slow moving disaster but that eventually he’s going to hit some type of wall and not be able to continue on pretending everything is fine. Conversations to try to help him or make him see reality have been unsuccessful. Having a frank conversation with him is like nailing jello to the wall.

My question is, how do I explain to him that we are not going to be living with him on the next lease cycle without destroying our friendship or setting in motion an emotional collapse from him, while also making it clear he needs to take this seriously and make plans on how he’s going to house himself going forward. I’m worried about having to spend the next several months with an angry and seriously depressed roommate or alternatively him in a panic come the end of the lease when he’s done nothing to prepare. I do feel like I have some responsibility to preserve his mental health and our friendship in all this.

Thanks,

Failure To Launch’s Roommate

Dear Failure To Launch’s Roommate:

The “As a friend I’m concerned about you for x reasons” and the “When the lease is up, we’re going to go our own way” conversation need to be two separate conversations. The less you cross these streams, the better for everyone involved.

I think that the best plan is for you and your partner to make a plan to move to a new “just the two of us!” place and to communicate it that way. “Hey [roommate], when the lease is up on [date], Partner & I have decided to move to a new place that’s just for the two of us.” That’s the cleanest break possible and takes “what happens to this apartment” or “Hey, we’re going to stay here, minus you!” off the table.

Sometimes we have to deliver news to people that they are not happy about. Undoubtedly, your roommate will have feelings about that. Rejection. Abandonment. Worry about finances and where he will live. Those are not your feelings or worries to manage right this second, if ever. Your job is to give him the information he needs to make a good decision about what to do next, without commentary on how he lives his life. It will work best if you are sure and you communicate it as a decision that you’ve already made. It will work best if you keep it simple and direct and focused on what you need (vs. digging into his issues or feelings). Trying to soft-pedal it and leave the door open to the idea that you might reconsider will not help him (unless your intention is to help him avoid things even longer).

Keep repeating this script. “We’re ready to live in a place where it’s just the two of us.” “It’s not about [him][whatever he’s shame-spiraling about], it’s just, we want to try living in a place where it’s just the two of us.”

Also, please keep this in perspective: You’ve lived together for less than a year. He lived somewhere before he lived with you, and he can live somewhere else again. Lots of people have roommate situations with friends that don’t quite work out. Lots of people find that they are better friends when they don’t live together. This guy could find another roommate situation. Moving in with a relative for a while wouldn’t be his first choice, but lots of people have to live with relatives for a while while they get back on their feet. He’s lucky that he has a safe place to go and it doesn’t have to be forever. He may catastrophize about this but please don’t let guilt drive you to reconsider a decision that you know is good for you.

So, tell him the news. Keep it simple and direct. Keep it focused on you and your future goals – “We’re going to find a place that’s just for the two of us!” (versus “We can tell that you don’t have your shit together and it’s stressing us out, so we’re leaving.“) Be crystal clear about timelines, money, dividing up stuff. The more direct, clean, simple, and candid you are, the kinder it will be.

After you tell him the news, be a friend to him.

Invite him to do fun things with you/seek his company in enjoyable ways. Keep the happy roommate rituals, like watching favorite shows together, going.

He’s a friend of both you and your partner, so, maybe take turns seeking him out one-on-one and break up the HAPPY COUPLE!!!! vs. THE ALONE GUY WE ARE ABANDONING dynamic a bit.

If he’s upset and needs a shoulder, listen to him without trying to solve him or fix him or “nail jello to the wall.” When you do comment on stressful stuff he tells you, do it in a way that affirms his agency in the situation. “Wow, that sounds like an awful feeling. What do you think you’ll do?”

Take him out of the “this is our sad friend who we help” role by asking his input or advice on things he is good at. “I need to redo my resume, will you take a look at it for me?” “I’ve never run a D&D game before, can you help me get started?” This is something the mutual friends can get in on, too.

Maintain boundaries. Don’t let him get away with mean or shitty roommate behavior just because he’s upset. Your communal agreement still stands as long as you live there, so “Hey, can you do your dishes by tonight, thanks!” is still a valid request even if he has sadfeels. Walking on eggshells helps nobody.

Maintain boundaries. It’s not your job to find him new roommates or a new place to live. It’s not your job to solve his career situation or his finances. It is okay to encourage him toward sounding boards who are not you when he’s upset about the pending move. “I know you’re upset about that, and I’m sorry, but I think this is maybe a conversation for your therapist or other friends, where you can safely vent!”

There’s no perfect way to handle this that won’t upset him or affect your friendship. You may indeed be for a rocky couple of months. If he’s unhappy in his life, you can’t fix that by…staying his roommate forever? By…delivering the news that you’re leaving in a way that’s dripping with concern for his emotional and financial health? It’s just not possible. Sometimes living situations don’t work out. You will be happier when he’s not your roommate anymore, and it’s okay to want that and to choose that. The best thing you can do for him is to own your decision. Be as clean and direct as you can and give him plenty of notice. From there, do your best to remind yourselves of the things you like about him and disengage from the rest.