Evening! So I got a little dilemma. About a month ago, a friend of mine from my hometown came up to Chicago to move. Like I did a couple of years ago, he came up here to find more opportunity, and so I let him stay on my couch. Now, I kind of want my entire apartment back, but I can't exactly kick him out as of now, he doesn't have a job and won't have anywhere to go (going back to his parent's house isn't an option for him). 

For the most part, he's been a good houseguest.  He offered to pay half my rent.  I took the money for February and March shares because I had been unemployed and that money helped me out big time.  I just started a new job and will regain the ability pay the rent wholly without any help onwards.  But since he's moved in, the toilet paper usage has multiplied that's it's stopped up the toilet, he's broken two glasses, and brought Tinder dates home to spend the night (I affirmed that the couch I paid for has to be cleaned).  All minor stuff I know, but I kind of want my one-bedroom space back, but here's the thing: I do want to retain the friendship.

We were originally thinking of renting a house with another friend in June, when my lease expires, but due to some developments with my life, I don't have the means to get one in time for that.  Right now, he's sleeping on my fold-out sofa, which really isn't a practical long-term sleeping solution.  So that's off the table for at least another year.

Here's what I think is best to do: wait for him to get a job, and he's been applying and interviewing like crazy, then subtly encourage him to find housing or a roommate situation that is closer to work.  He doesn't own a car, and though Chicago has great public transportation, it's a huge city and in some cases, it makes sense to live in a neighborhood closer.  As I mentioned earlier, I took his offer to pay the rent for February and March because of my unemployment, and now that I have a job, I'll stop accepting rent money starting in April.

Does that work? Any other suggestions? Also, when shall it get to a point where I have to be more of a "landlord" than a friend?

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Maybe you should have set some kind of limit from the outset, like "You can stay for a month, and after that we'll talk about staying longer."

I can't speak for your friend, but I always appreciate directness and honesty, even when it hurts. Or you could try this:

Fair enough, but I'll wait unit he actually gets the job until I get that honest. I know he's frustrated with the employment search process.

You've already been a really good friend to him, in my opinion. I think it's fair to say, "look - It's been cool having you here, but this is a small place, and I don't want this to become an issue in our friendship, so we need to start to think about where we go from here" - start talking through plans for when he gets a job, and worst case scenario, if he doesn't. But keep it a conversation, you want his input, not to make ultimatums. 

Ah man, I do not miss my bachelor days much at all, and roommates are the main reason.  I had seven roommates in 10 years, and only two of them were guys I enjoyed living and hanging out with.  As for your situation, I think Liam gave you some excellent advice.  The fact he has offered to cover half your rent is a good sign of the kind of character he has, and IMO, you should continue to accept it from him, regardless of who's employed and who isn't.  And he should continue to offer.  The things you mentioned, like the TP and broken glasses are just living pains that come with living with someone.  But definitely discuss the near-future for both of you and draw up some kind of plan that either encourages him moving into his own place or the two of you getting a bigger place.

I had a friend who said you get 3 days as a guest then you are a housemate.  When I stated with them on the weekends I would help out around the house and pay my share (more really).  It actually helped to have the understanding clear.

The things broken need to be replaced.  Letting them know it's not cool to have a date randomly stay overnight is beyond fair.
Still if they are interviewing and not lazing about they are trying.

It sounds like a few beers and a frank discussion should correct the issues. 

Yeah, he's trying. I'm at work, he's actively looking for work, I give him lots of credit for that.

I had a similar situation many few years back and after a couple of months I told my friend it was time to find another place to live (giving him 3-4 weeks).  He just had a couple of suitcases so finding a place and moving was straight forward.  In his case, finances weren't an issue, but if someone is close to homelessness, chances are they need more resources than you can offer.  I also focused on helping him find some furniture and stuff at resale shops to get him started and there wasn't any hard feelings.  

As time has passed, he hasn't made efforts to stay in touch. I think we both consider each other more a friend of convenience over a close friend, so I'm glad I could help him out when he needed it and set my boundaries when I needed it.  

The only thing I'd feel stronger about is the Tindr dates.  I personally would feel vulnerable and angry if someone invited complete strangers invited to my home without my consent--it's not their right to do so.  

That sounds very similar to what I got. I'll wait for him to get a job first before I have that conversation.

You know, we could merge this with the "Shirtless around women" thread and end up with some disturbingly outside-the-box ideas!  (Except that this houseguest is a dude.  Ah, well.)

Easy squeasy.

Have a bunch of beers with him one night. Get all juiced up.

Look him in the eye and tell him that you need to shag him, right here, right now, and make sure your look conveys you have every intention of doing so any minute.

You'll either gain a nice roommate with benefits (if you are into that sort of thing, I can never assume anything these days), or the next morning you'll find the note from him saying it's been a blast but he had an aunt suddenly take ill that he has to leave to take care of. In the future you would of course deny the whole affair, saying how drunk he was.

LOLOL

Carl wins the thread.

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