I know this is riske but let's speak realistically and honestly.

I rented to a single mom and since Day 1 I feel she has been flirting with me.

Like she wants to hook up or something.

London, Ontario is basically a graveyard for older guys to meet women.

Has anyone ever dated their tenants?

Honest question folks. I'm sure I'm not alone in my passion.

This is a no brainier! You can NOT date a tenant unless you are willing to give up on collecting rent! With over 100 units over the years I had many opportunities to date my tenants....couldn't, wouldn't and shouldn't.

Collecting rent is overrated.

How attractive is she? How flirty?

You do have the advantage of having run a background check, credit report and criminal search on her. I'm sure that's more information than you would get from a typical date.

Well......

For times like these, you have to develop yourself a flow chart of sorts.

#1. Am I married or single?

A. married, STOP go home and take a cold shower.

B. Single, proceed to question 2.

#2. Am I in this business to be a professional landlord or investor or do I just own a duplex with an empty unit next door.

A. I am a professional, STOP go home and take a cold shower.

B. It's a duplex, I don't she's hot and I'm single!

You get the idea.

Just know if you get to the point where you answer B at question 2, she's no longer your tenant and it will probably end poorly.

I worked for an investor in Philly years ago when I was first learning about RE. He was an older guy who was single and had a ton of units.

I was working in a really nice 3br rental of his and this younger rough around the edges but attractive single

mom starts moving her stuff in. I asked the other helper there who had worked for the guy for quite some time how on eart is she able to afford that unit.

He laughed and said "Come on man, she isn't paying any rent!"

So it happens. The good old barter system. That's life. That's reality. Just prepare for the fallout.

Not for me though. I was in it for the RE long before I met my wife. I was never interested in Real Estate with Benefits.

It may be a new marketing angle!!!

Free Rent!

YOLO(you only live once)

Would you rather be right or rich?

If I were him, living in a graveyard, I will get the relationship going, once it’s ripe. Move her to your flat. She lives rent free, you got someone to warm your bed.

Win-win.

As a LL, it’s my passion to solve the in-solvable.

All moral considerations aside....if you're giving someone a tangible benefit (i.e. free / reduced rent) in exchange for sex...that could (mind the word "COULD") be viewed as any or all of the following:

1) Prostitution

2) Employment

3) Contact work

Etc.

It will all depend on what type of lawsuit she decides to file against you after the break up and when the last time your judge was jilted / how bad the last break up was / if he/she hates men at this particular moment in life (notice how gender inclusive I was there?).

Did I just assume that it would go poorly? ;-)

Can She Swing a Hammer, run a Saw

and carry 2 Bundles of Shingles

up the Ladder ? ( 1 on each shoulder )

Do what Ya gotta do.

Who knows ? One time out might decide Your Future !

Never stop looking for Love.

"Some like it Hot".

All joking aside, it boils down to what Sid said.

When I was single and renting an apartment, there was a single hottie who lived downstairs. I was telling a co-worker about her and said, "Even rats don't ______ where they sleep."

"Collecting rent is overrated."

"KINGPIN"

THANK YOU FOR KICK STARTING MY DAY OFF WITH A GOOD LAUGH!

...actually, a friend of mine was a young single professional woman. She rented an apartment from a young single guy landlord. The rest was history!

They got married and are still together 20 years later!

Haha Julie!

Geoff London [ON]), What is your net worth, IF you know, that's great. IF NOT then add it up everything you own real estate, stocks, bonds, retirement. NOW what's your bottomline. NOW do not disclose this amount on this board. Just keep it to yourself.

HOWEVER, once you start a relationship with this Lady, you will be asked by the judge in court after she sues you for every dime you are worth!!!

As NE of PA says take a cold shower THEN pack your self in ICE to chill out. Then go grocery shopping you may meet someone there. ANOTHER thought would be apply for The Bachelor, the TV reality show. A great show to make a fool out of yourself to entertain the viewing audience.

Have you not been reading about Weinstein and others in the media due to sexual harassment. Let's just add Geoff to the list now because I guarantee you, you are opening yourself up to a bad situation.

Another option. IF Canada has a 1031 exchange similar to the USA. Your tax burden on the property is deferred to another property. ANYWAY, IF you are in the back country of Canada and have not seen a female in years. A perfect 10 that is then move to the big city. Grocery shopping, church, singles group, friends, online dating. HOWEVER a landlord dating a tenant is the worst idea.

Take another COLD SHOWER, the unit the lady is living in consider a property management company to manage the unit while she is renting the unit.

Another option if you are living in the back country of Canada and you have a lake nearby and the water temp is lower due to the winter. Consider taking a swim in the lake to CHILL OUT. HOWEVER be Careful of FROST BITE so MAYBE a cold shower is your only choice at this point to CHILL OUT!!!

NOW if you are still considering dating your hot tenant, take a cold shower. SPRING BREAK is fast approaching take a much needed vacation to the best Spring Break locations, while you are there look at properties for rental potential; then the trip could be considered a tax write off for you. You may want to consider remodeling your bathroom with a walk thru shower, similar to a car wash...

Happily married for 39 years, so my advice may be biased...

Never no never no never mix personal and business. You could lose everything.

If she's that attractive to you, help her move elsewhere (to a nicer place of course) and THEN date her.

A local LL accepted the advances of his young attractive tenant. She told him the following month "no more rent money, only sex from now on".

After six months his wife was demanding to know why they were missing the rent money every month...

He almost gave away this property (sold it really, really cheap) just to break the ll/tenant relationship.

It could have cost him much, much more.

Ew. I bet she's a petri dish of std's, if that's her normal default mode for financial transactions...

You realize, if you accept "rent" once, you can never accept real rent again? So when you decide your bank account would prefer a tenant who actually pays money, you'll probably have to evict your tenant who's not paying money... and she's not going to want to give up infinite free rent... and then you get to take her to court... and then everyone gets to laugh at you when she tells the world about your arrangement... and then you get busted for solicitation, or whatever it's called.

So, how much is rent per month? $1,000? $2,000?

I presume nothing she can give you in the course of a year is worth $12k. Or $18k. Or whatever the number is.

Geoff,

In the words of the noble Canadian philosopher Red Green

“If the ladies don’t find ya handsome they better find ya handy”.

So are you handsome or handy?

BRAD

PS No way. Too many legal issues when mixing a business relationship with another tyoe of relationship.

And with all the me-too accusations destroying men’s careers...

She may not be flirting with you. She may just be friendly. Not every single mom is looking for a daddy for her kid or a sex partner for her bed.

And if YOU act on what you think are her signals, and you misconstrued them, you are now the creepy old landlord pressuring the tenant to have sex. Bad in every way you can think of.

Well I have had cause to go through London, ON a time or two and I would disagree with it being described as a graveyard. Its a thriving university town. There are lots of social groups, churches and other organizations. Dating flirty tenants would appear nowhere on my list of conceivable options however. This is a road to endless trouble and regret.

If you pursue it, you will never be able to evict her.

If you want a paid mistress, pay her rent to another LL. then, when you break up, you stop paying the rent, and she is that other landlord's problem.

If you sleep with your own tenant, it could mean free rent forever! Especially in this day of #MeToo!!!!

Reminded me of the Seinfield episode where Jerry starts sleeping with his housekeeper. Pretty quickly she stops cleaning but still wants to get paid.

My first thought was what the hey, maybe is not a terrible idea. If all you are looking for is sex, then find a professional. Charlie Sheen said he didn’t pay hookers for sex, the payment was for them to leave after sex. But if you are looking for a Long Term Relationship go ahead. Take it slow. Keep sex OFF the table for a while while you see how it goes.

After thinking about it a little more, Don’t Do It. Use the energy and excitement that you feel when you think about her to get out of the house and go do something where you can meet other single people. This would be much more productive with a lot less risk.

It's a mistake, as they all tell you. Men with the hots for a woman tend to mislead themselves about the woman flirting. You see what you want to see when you let Richard rule.

I have a different view. Alsothough it's is a good policy to eliminate all tenants from dating, it can work out well on an individual basis.

I believe it depends on the maturity of the tenant. In my 20's I once rented FROM a nice young lady and we did get romantic, but once never thought once thought about not paying rent. So since I was mature about it, there was no problem at all.

My wife and I keep our money separate and she is mature enough to offer me money when I work on her rentals, etc.

You have to be careful with some of these middle aged unattractive guys who are renting to students. My daughter was harassed while renting a small house by her landlord.

She was a Grad student. He saw her as an easy mark because she was living alone and so busy with her studies.