My sister’s unemployed boyfriend is lazy, creepy and rude – plus, he lives in her house for free

The Question

About three years ago, my boomer parents helped my millennial sister purchase her first home. Shortly after, her unemployed boyfriend moved in. She has confessed to us that while he is allegedly working on developing a video game, he does not help out financially with housing or food costs. In the past, he has told my family he refuses to work for someone else. Recently, my sister's employer laid her off.

Instead of looking for work, she started a business, which has yet to break even. My mother's name is on the mortgage, so she routinely helps my sister with home repairs, credit-card bills and other costs.

My mother refuses to remove herself from the mortgage should they become common-law and the boyfriend takes half of everything.

My parents and I agree that it is not reasonable to support her and, by default, her boyfriend. He's lazy, creepy and rude.

My sister no longer lets me inside her house, as she says he does not approve.

When my father last visited, a year ago, he was concerned by the number of Scotch bottles lying around, by the fact that her boyfriend was watching sports in the middle of a workday and by the extreme mess the house was in. How can my family help her?

The Answer

Yikes. These types of situations are all too common. I read somewhere that around 40 per cent of Canadians between the ages of 20 and 30 still live with their parents.

Let me say, before I go any further, that one's twenties are a difficult time, no matter what millennium one is from.

I knew what I wanted to do (write), but many of my peers didn't, casting about, trying this and that, until they found their métier.

But, yeah, loafing around a messy house watching sports while dropping empty bottles of Scotch on the floor in the middle of the afternoon on a workday? That is not a good look in a son-in-law.

It's tough, though, to know what to do when you have a character such as this in your midst, whether in-law or direct offspring. My boys are teenagers now (well, the oldest is 20) and, of course, I don't want to picture them homeless, curled up like a shrimp on some steam grate.

Traditionally, you kick kids out of the nest at a certain point and they make their way. They rent a place with, say, three friends – that's what I did. That's what you did. That's what you do.

And there's no denying, or point in pretending: It was horrible! What's terrible about living with other dudes is the other dudes' other dudes – you enter your kitchen and some guy you've never met before, standing there in his underwear, is making a peanut-butter-and-jelly sandwich and you're like, "Hello? May I help you?"

And he's like, "Nah, I'm good." Flexing his buttocks in his tighty-whities as he walks off munching his PB and J. So you stare at the man in the mirror and think, "God. I have to get my own place."

And so you do. Gradually, independence is achieved.

Bottom line: I get why you might be worried about your sister. I say this as a parent: It's tough and it's easier said than done, but you have to let your offspring make their own mistakes.

I'm wondering why you're so worried about your sister and her relationship with your parents. Could there be an element of envy?

In any case, I would file the whole thing under H for "Her problems." You have to let her make her own mistakes.

Having said that, it may be time to have a chat with your sister, if she would allow such a thing to happen.

I said what I had to say about being in one's twenties, but it's also a period where you're figuring out what you want to do in life.

Were I in your shoes, I'd say, "Listen, sis, this is obviously not an ideal situation for you vis-à-vis this weekday-afternoon-sports-watching, empty-Scotch-bottle-dropping boyfriend of yours. Is there any way to get him to step up his game, or explain why he can't?"

Of course, you could get some push-back. Your sister might be all, "How dare you?" But this is what we do, as family members and friends. We dare to care. We annoy the people we love because we care.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.