Obligatory 'not today but several years ago' (2001).

So I was 26, living alone, trying to establish my career and get my life moving in the right direction. I was renting a basement studio apartment that was technically shorter than my physical body (my head brushed the ceiling in half the space, and on more than one occasion I banged my head against a duct bulwark). Whatever, it was cheap.

So I'm doing my thing, living, going to work, etc. At the time, my mom worked for a condo developer in their customer service department. New condos came with a warranty in Ontario and if homeowners complained my mom was there to organize bringing the problem up to snuff (or gently explaining to people how their best course of action might be to engage in autoerotic misadventures and cessation of respiratory activities).

In the course of her work, my mom met a lot of real estate agents. People who bought these condos would very often flip them for considerably more than they paid, because they put up large deposits during construction that we plebes couldn't afford. So once the buildings got built, they'd sell their new place to some schlub who didn't have a 20% downpayment, but could mortgage himself into the next lifetime for a chance to be a homeowner (ah, the beautiful run-up to the crash of '08).

By their nature, real estate agents tend to be pushy. When your paycheque depends on convincing other people to spend ungodly amounts of money they don't have on a home that isn't necessarily 100% perfect, you have to have a thick skin and an inability to hear or understand the word 'no'. And of course, these people are ALWAYS looking for their next meal ticket client in every seemingly casual conversation. So my mom, who is actually desperately insecure and needs people to like her and think she's cool, mentions to this one particular real-estate lady that her son (i.e. me) is living in this much-too-small basement apartment because he can't find a decent condo in the city. Offhanded. Casual. Not really serious, more just making conversation.

Well.

This woman decided that her new mission in life was to find the Perfect Condo^TM for me. And she brought a list of places to my mom for me to look over.

Now, bear in mind, I have no idea this is happening. All I know is, I get a phone call from my mother that I'm seeing a condo on such-and-such Friday. Uh, what?

Now, like my mom, I also have a deep and abiding need to have people think I'm a decent human being, so rather than embarrass my mother in the eyes of this pushy near-stranger (to her, I've never met this woman in my life), I decide I can sacrifice one evening of my oh-so-busy social schedule to put in an appearance and save face.

So we go see this place, which is actually not horrible. It's tiny, a junior one-bedroom of maybe 200-300 square feet (essentially a living room with a shelf where the "kitchen" sink is, a bathroom and a little bedroom through a set of folding doors). Smaller in square feet than the apartment I'm renting now, but at least my head is un-banged. However, my mother, in her haste to prove her worth to this property predator, has completely overlooked the fact that I do not have a downpayment, or enough cash flow to service both a mortgage AND the condo fees associated with living in this hole-in -the-wall.

Undeterred, my mother, in her infinite wisdom, suggests to me that I can somehow escape this situation by pretending to be a serious homebuyer and putting an offer in. Now of course, this can't be a reasonable offer - they might accept it. Just lowball them, offer something insultingly low, they'll say no, but hey, at least we tried, no hard feelings, yadda yadda yadda.

What she had failed to take into consideration was that this property had been on the market for an EXTREMELY long time, due to its "unique character" and the seller was motivated. So motivated, in fact, that when they received my offer of 25% below the asking price, they accepted it anyway.

This all took place in less than an hour. I have spent more time weighing what to have for dinner than I did this binding real estate purchase. But I'm Canadian! Gotta be polite!

So I took a loan for the downpayment, moved in with my mother, and rented out the condo so I would be able to make the whole thing work financially. It was to be a temporary arrangement to tide me over until I paid off the downpayment loan, then move into my cozy bachelor pad. But trying to rent the place was a nightmare (which involved at one point me arguing with a prospective tenant that no, a one-bedroom apartment does not necessarily include a kitchen, a one-bedroom apartment must only feature one bedroom in order to meet its trurh-in-advertising requirements) and when I finally DID manage to find a tenant, he paid a grand total of two months' rent before stiffing me, which forced me to evict him and put the property up for sale again six months later.

I did manage to sell it, at a tidy profit (poor schmuck) and moved in with my new girlfriend shortly thereafter. Believe it or not, I still speak to my mother.

TL:DR Put a lowball offer on a condo I didn't want, to be polite - it wound up being accepted.