my (soon to be ex) roommate is driving me crazy!! (apartments, lease)

[groar]

ok this is long and i forgive anyone who doesn't feel like reading it.

my husband and i own a house, and a friend of his needed a place to stay in july of 2009. we have a third floor we don't really use, so we agreed to let him move in. the general impression we got was that he was going to live with us for a while until he bought a house or found an apartment of his own.

we didn't put anything in writing when he moved in, we just did the default month to month lease. he didn't pay any deposits, he just started paying the rent.

so, a little over a year into this, we decided we were really sick of having a roommate. he's an annoying dude on a lot of levels but what it comes down to is we wanted our privacy, and were sick of the dog barking at the door when he came home at all hours, things like that. so, in mid august we asked him if he could move out by the end of november. seems like a pretty generous amount of notice, right?

so, in the ensuing months it became increasingly clear that he was not going to find a place. he kept vacillating between renting in our city, buying a house (but with massively unrealistic expectations), moving to another city, even moving back to his home country. he looked at 2 apartments in the month of november (none before that) and both of them were in ridiculously far out places that weren't the kinds of neighborhoods where he wants to live and were super inconvenient for getting to his work. he could live in pretty much any neighborhood in the city even with his low price range if he had a roommate, but instead he's looking at roommate situations out in the suburbs on the opposite end of town from his work. i do think he was intentionally sabotaging his apartment search, at least subconsciously. he never even approached us to ask if he could stay beyond december 1, he just kind of stayed and didn't say anything.

so, on december 1 we served him with an official 30 day notice. he was all like "why do you have to make this official, aren't we friends" and i said "we asked you nicely and gave you a huge amount of notice and you clearly didn't take it seriously, so maybe you will take a written notice seriously".

so, yesterday he e-mails me and says "i'm going to sign a lease on an apartment today, please use my first month's rent fee to pay for december". i write him back and tell him he didn't pay a deposit so he had to pay for his last month's rent. he keeps arguing back with me. the basis of his argument is this:

1. when you pay rent, you are paying for the previous month's tenancy.
2. he paid at the beginning of the month when he moved in, therefore he has an extra month's rent to put toward the last month.
3. therefore, the rent he paid in november covers him til the end of december.

we went through a huge argument trying to make him understand that he was trying to give us 17 months' rent for 18 months' tenancy. that even if he looks at rent as covering the previous month (which is insane in itself), that he then owes us for november, since by his reckoning november's rent covered october. we took little pieces of paper to represent months and covered them with dollar bills to represent rent, condensing it to 4 months, and he still couldn't comprehend how 3 rents didn't cover 4 months. he kept saying "it's possible i might be wrong, if i'm wrong i'll pay you" and insisting he had to ask a professional landlord if he was right or not.

he finally gave in and gave us the damn rent and i THINK he realized he was wrong. he also cried, while basically making us look like jerks because we finally confronted him about all this crap and wouldn't acknowledge that his blatantly incorrect ideas might be correct. but i'm still kinda worried he's going to call some rental agency and confuse the hell out of them until they say something that makes him think he's right.

i don't know that we'll ever rent out our third floor again, but if we do we are DEFINITELY going to lay things out in writing at the beginning. i don't know if that would have helped though - i mean i don't think we would have thought to put "rent pays for the upcoming month and you can't use one month's rent to pay for two months of tenancy".

so now we hopefully just have to deal with him getting his stuff out. he's going on a trip from late december until mid january and wanted to leave his stuff here, and my husband felt bad and wanted to let him do it, but i really don't want to do that. it just seems like asking for more hassles. plus we'll be gone when he would be moving out, and while i don't think he'd do anything shady, he will almost definitely accidentally let one or more of our cats out and there won't be anyone there to let them back in.

oh and also, he wasn't going to sign a lease. he was going to fill out an application. he has no other options on the table. but i really don't care - he can live in a motel if he can't find a place before january.

[ShaneSA]

Considering your goal is to get him out, I would insist he leave and take his things with him. Do not allow him to move while you are gone. If you are away, all you will do is worry that on your return he will NOT be gone and he will have done damage or theft.
Tell him to get a storage unit and get his things out. And be sure to change all the locks. He may give you a key, but who says he hasn't made copies.
It sounds paranoid on my part, but I've been there and you need to make things proper for yourself and comfortable for you. Someday he may figure out how to live and make right choices. It is not your responsiblily to teach him.

[SCDQ]

What Shane said!!!!! What Shane said!!!!!!!

People will take advantage of you as long as you allow them to do so. Do not be moved by tears, etc. He's trying to play you. Hang tough, follow the law, do NOT give him any special considerations because you *think* he will be leaving you soon!

[STT Resident]

Ditto. He and his stuff have to be out by December 31st, period. As soon as December 31 comes you have the locks rekeyed (it's not expensive) and if anything of his has been left behind then you give him written notice that he has x amount of days to pick it up at a mutually convenient time. Google "(your state) landlord tenant laws" to see what you can legally do if he leaves things behind, i.e. how long you have to to hang onto it before disposing of it. In future, familiarize yourselves with landlord tenant laws and don't rent out that space again until you know what you're doing. Good luck!