I moved into my new Canadian apt in April and my landlord asked me for post-dated cheques for 12 months. I negotiated and gave him 7 instead and he said he would need the remaining 4 at the beginning of the 8th month. I know it's not mandatory and it's against the law to DEMAND pdc's but I still obliged.

Now, I've been grinding live poker regularly alongside my job and want to pay him rent for the pending months (June-Oct) I've given him cheques for by CASH instead as I'm doing pretty well in live poker recently but don't feel comfortable depositing >2k/mo in cash at the bank although I know those poker winnings are non-taxable.

My landlord is very jovial and does know that I play poker at the casino regularly. I've also offered him my comps sometimes. But I'm wondering how I should approach him to ask if I can pay, say June's rent, by cash and ask him to return the cheque?

I don't want to just say -- "can I pay June's rent by cash?" and make him wonder why. Can I be upfront and tell him I have some poker winnings with me so want to pay cash if that's okay? Or would it bother him/make him suspicious?

Why the hell would you agree to give him 7 months worth of post dated checks?
Not sure about lolCanadian banking regulations, but my bank here in USA#1 will process a check immediately regardless of the date printed on it. They don't care if its post dated or present dated.

Is it normal in Canada to pay your rent for a full year in advance?

No, but I gave it anyway in good faith and understanding as it didn't seem like a big deal to me as he promised me he would never deposit them in advance or anything, and it was just more convenient as he wouldn't need to approach me in case I didn't pay on time. I guess it was a way of him feeling more secure as I didn't have a job at that time.

Regardless, that's not my concern though. I'm just wondering if asking him if I can pay by cash for June (and later, July-Oct) would look weird now.

Everything seems fine and you seem to have a good relationship with him, and then you just collapse at the thought of telling him you have spare cash and would like to give it to him for rent?

Of anyone, a dude who illegally asks for checks up front should be a-ok ripping then up and taking cash.

Well, I'm just not sure how to put it across as I've not come across such a situation before. But yes, I like your reasoning.

I need to give him some reason instead of just saying "spare cash" though, as I want to do it for the upcoming months too, right?

"Hey man, poker has been going pretty well. Could I pay you in cash for the final 4 months instead of the checks you have?"

"That's good to hear. Why not just deposit in the bank though and have me withdraw via the checks?"

OR

"No, I prefer checks."

Possible?

Tell him you are closing your bank account and the checks are no good.

You're way overthinking this. You ask him if you can pay cash. Use Larry's line if you want or if he asks why. He's either okay with it or not. There's no magic way to ask that's going to make a difference in how he responds. Maybe if you're the only tenant he'll take cash, but no place I've ever lived would let you pay cash for rent as landlords don't want to have to deposit thousands in cash every month any more than you do.

I mean, he'd have a pretty good point.

"My life as a Canadian poker pro, or How I failed to convince my landlord to help me launder some loonies."

Yea if he decided to be a stickler on you there isn't much he can do.

If you think based on his personality that he might say no when presented it as an option, you could say, "Hey I'm gonna pay you in cash for these next few months I stead of the checks, let me know when you want to swing by."

I didn't get it. What does that mean?

Well, in Canada, it's illegal for him to demand checks. I have liberty by law to pay cash.

I thought you needed to be conniving to make money in da pokerz these days? OP has 0 connivings.

I live in Canada and my leases have always said payment by cheque or money order only, but you seem to be correct.

Instead of phrasing it as a question: "can I give you cash instead"

Present it as a fact, "Hey I'm giving you cash instead"

Some % of the time this will avoid someone saying no because it's a choice offered in the 1st case.

Yeah-- but it just looks a little rude to assert it, the first one is a better option right?

nah. it's stronger communication to let him know exactly where you stand.. if you pose it as a question, he might think you are indifferent and not wish to change his schedule.

on the bright side handing him an envelope with $$ should work almost always. you can even get creative and say something like, "Cousin Sal got an early release and I got him a place upstate, not an easy thing with the banks. Oh here's a fistfull of cash for rent this month, will this be okay?"

I don't see the upside of paying in cash if you trust this guy (which you seem to). Why not just deposit rent into your account and pay it?

You seem to realize this already so

Laws regarding tenancy are based on the province you reside in. In BC it is totally legal
for a landlord to require 12 months of post dated checks if it is in the tenancy agreement.

In Ontario it is not allowed.

So a text like "Hey XYZ, I'll be paying the June rent by cash if that's okay and you haven't deposited the check yet as I have spare cash lying at home. Can you come collect it tonight please? Or I could drop it at your door if you like." seems fine?

I'm in Toronto, ON.

grunching,

Why are you offering your comps to a dickwad that makes you give him post-dated checks?

easiest way is in person and use this script:

XYZ, Can I talk to you about June rent?

(yes)

I have it in this envelope. Pulls out envelope stuffed with money. Is it okay if I pay you this instead of the cheque? I've been moving bank money around and this would be easier for me.

--

If it must be text it doesn't matter what you say, though I'd remove the part about asking him to come to you and do whatever means necessary to make his job easier.