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Woman Says No to Best Friend’s “Win-Win” Plan After Realizing She’d Carry All the Risk

by Charles Butler
December 22, 2025
in Social Issues

Friendships that last decades often come with an unspoken belief: trust is automatic, and boundaries don’t need to be spelled out. But sometimes, the longest friendships are tested not by malice but by entitlement disguised as a “helpful idea.”

In this case, a woman preparing for marriage and a major life transition suddenly finds herself defending her most valuable asset: her fully paid-off condo. What starts as a casual lunch proposal quickly turns into a lesson about consent, responsibility, and how “no” can become invisible when someone wants something badly enough.

As weddings, relocations, and blended families collide, one question hangs in the air: Was this really a win-win situation or was someone quietly volunteering another person’s home for their own convenience?

Woman Says No to Best Friend’s “Win-Win” Plan After Realizing She’d Carry All the Risk
Not the actual photo

Here’s The Original Post:

'AITA for not letting my best friend take advantage of me?'

This is a throwaway account. My best friend Diane and I have known each other since elementary school.

Diane is dating Roy, he has two teens who stay with him half of the time. I'll refer to them as Diane's step kids. Now on to the issue.

I'm getting married in six months. My fiance lives in another state and I’ll be moving to live with him.

I own a condo, fully paid off, and I’m keeping it so I have a place to stay when I come back for work meetings and visiting family.

My fiance also has family here, so I estimate we will be back here every other month, more or less.

Diane agreed to hold an emergency key, in case maintenance needs to access my condo. I thought I had everything settled until two weeks ago.

Diane and I met for lunch and she says she has a proposal for me. Her stepson goes to college near my condo.

She says it would be good if stepson condo-sat for me. That way I wouldn't have to worry about the place when I'm not there.

He would pay me a small stipend each month to cover any wear or tear. He will stay with his father whenever I'm in town.

She says it will be a win-win situation as I will be making a little bit of income on an apartment that would otherwise be empty.

In a split second, I imagined all the liabilities I’d be exposed to by having a very social college kid living unsupervised in my home.

Coming home and having to clean up behind him, complaints from neighbors, and my poor bed. Nope.

Honestly, just the idea of anyone living in my home when I'm not there is unappealing.

So I thanked my friend for the idea and told her I just didn't want anyone living in my condo.

I wanted to be able to come and go as I pleased without worrying about it.

She kept pushing the issue, telling me why it is a great idea, with me telling her no and reasons why.

Finally, she said that on the basis of our friendship would I at least think about it overnight.

I told her that she was basically asking me to take on a tenant and all the financial and legal responsibilities that come with it.

So if she truly believed this was a good idea, she and her boyfriend will have to sign a contract making them financially responsible for any and all liabilities.

She asked why did she have to be on the contract. I said I was only asking of her what she was asking of me.

She got quiet. I told her to think about it and get back to me. Roy later called me and said he would be willing to sign the contract.

I said Diane would have to sign it too, as she is the only reason why I am considering it.

I then explained to him why I wanted to keep the apartment empty. He told me Diane came to him with the idea and said she would talk to me...

he wouldn’t have bothered with it if he knew the full story.  It was a pleasant conversation.

The next day Diane called and said that I embarrassed her to her boyfriend.

I told her if she had just respected that I was not interested in her proposal, we would not have had this problem.  AITA in how I handled this?

EDIT: To be clear, I did not give her the key yet. I was going to give it to her closer to when I was going to move. I do...

The setup is straightforward. The original poster owns a condo outright – no mortgage, no financial stress tied to it – and plans to keep it as a home base when visiting family and attending work meetings.

That alone makes the condo more than just property; it’s security, flexibility, and peace of mind.

According to housing and financial planning experts, owning an unencumbered property is one of the strongest forms of financial stability, especially during major life changes like marriage and relocation.

That stability is exactly what her best friend Diane seems to see – not as something to protect, but as an opportunity.

Diane’s proposal sounds reasonable on the surface: her stepson goes to college nearby, so why not let him “condo-sit”?

He’d pay a small stipend, stay with his father when the owner visits, and keep the place occupied. Framed this way, it sounds efficient. Helpful, even. But efficiency for one person can mean risk for another.

The moment the idea is examined realistically, the cracks appear. Allowing someone to live in your home – even temporarily – creates a legal landlord-tenant relationship in many jurisdictions, regardless of how informal the agreement is.

Housing attorneys often warn that without a formal lease, property owners expose themselves to risks ranging from property damage and noise complaints to insurance complications and, in extreme cases, tenant rights claims.

The OP immediately recognizes this. She imagines coming home to mess, neighbor complaints, wear and tear, and the emotional discomfort of someone else occupying her personal space.

Most importantly, she simply doesn’t want anyone living there. And legally and ethically, that should be the end of the discussion.

But it isn’t.

Diane continues to push, reframing the refusal as something that just needs “more thought.” This is where the dynamic shifts.

Boundary experts often note that when someone keeps pressing after a clear no, the issue stops being about the proposal itself and starts being about control.

Diane invokes their friendship, subtly implying obligation. This tactic – appealing to emotional history rather than addressing practical concerns – is common in boundary disputes between close friends and family.

So the OP does something smart. She translates Diane’s request into reality: if this is such a good idea, then Diane and her boyfriend should share the responsibility. A contract. Full financial and legal liability. Suddenly, the enthusiasm disappears.

Diane’s immediate question – “Why do I have to be on the contract?” – is telling. Because in her mind, the risk was never meant to be shared. It was meant to sit entirely on her friend’s shoulders.

When Roy, the boyfriend, later calls, the situation becomes even clearer. He admits Diane pitched the idea to him without full context. Once he understands the risks, he acknowledges he wouldn’t have pursued it otherwise.

This moment exposes the core issue: Diane wasn’t advocating for a fair arrangement – she was advocating for convenience, assuming her friend would absorb the consequences out of loyalty.

From a psychological standpoint, this is a classic case of entitlement creep. The longer a friendship lasts, the easier it becomes for one party to assume access – to time, money, resources – without explicit permission. Diane’s embarrassment doesn’t come from being mistreated; it comes from being exposed. Her proposal didn’t survive contact with accountability.

The OP’s final decision – to revoke key access entirely – isn’t petty. It’s protective. Trust, once strained, requires rebuilding, not blind continuation.

Here’s the comments of Reddit users:

Reddit commenters overwhelmingly side with the OP, and for good reason.

CaliGrlNVA − NTA. You may want to change your locks though. She already has a key and might give him access anyway,

like “I thought once you could see how great it is you wouldn’t mind or would change your mind” or something.

Tamstrong − NTA. And after all that mess, I'd no longer feel comfortable with her having the emergency key.

moondream6 − Nta, it all makes sense. You trust her of course, but she's not living there.

A young college boy is living there, one you don't know very well and don't trust very much.

If they won't agree to you protecting something you worked hard to acquire, then you won't rent your home to a college tenant on "faith, and trust". I wouldn't do...

Many point out that “no” is a complete sentence. Others highlight the legal risks of informal housing arrangements, including squatter protections in some regions.

Big-Lab9018 − NTA at all. You said no multiple times, she kept pushing, and the second you put actual responsibility on her suddenly it wasn’t such a “win win” anymore.

She’s only embarrassed because your contract suggestion made it clear she wanted you to take all the risk so her stepson could get cheap housing.

baka-tari − Without a contract, you could be in for all sorts of shenanigans like squatter’s rights, etc.

If Diane really wants to pursue this, she should want to pursue it in a legally sound manner.

Your initial response of “no tenants” was solid, and your alternative solution makes sense - you want to reduce your risk as much as possible.

You told Roy the same thing you told Diane, so if anyone was embarrassing Diane, it was her for not telling Roy all the details. NTA

ThatsItImOverThis − NTA No is a complete sentence. If she respected you, she would have respected your answer.

Instead she kept pushing, even after you told her you were uncomfortable and not okay with it.

PastButton5106 − NTA at all. You said no, she kept pushing, so you laid out exactly what her “great idea” actually meant for you and suddenly it wasn’t so great...

She embarrassed herself by volunteering you and your home for a situation she clearly wasn’t willing to be fully responsible for.

Several note a deeper breach of trust: once Diane pushed past a clear refusal, she forfeited the privilege of holding an emergency key.

Ruebee90 − NTA. Get your key back from her.

allonestring − NTA. I do hope that you've found someone else to keep the spare key...

Lopsided-Beach-1831 − Change your locks and make sure you have a camera system inside and external.

Also, there are automated leak detection monitors for hot water heaters, under sinks, dishwasher, laundry that can be set to notify via wifi or actually shut the water off depending...

Just in since your condo may be empty for stretches of time.

The auto shut-off models also get a discount on homeowners insurance.

Some homeowners insurance sell them at a discount also, check in with your agent. Congrats on the wedding! !

True friendship respects boundaries, especially when they involve money, property, and long-term consequences.

The OP didn’t embarrass her friend – she clarified reality. And when reality made the proposal uncomfortable, that discomfort belonged to the person who tried to offload risk, not the one who refused it.

Sometimes, protecting what you’ve worked hard to build isn’t selfish. It’s necessary.

 

WHAT DO YOU THINK OF THIS STORY?

WHAT DO YOU THINK OF THIS STORY?

OP Is Not The AH (NTA) 119/122 votes | 98%
OP Is Definitely The AH (YTA) 1/122 votes | 1%
No One Is The AH Here (NAH) 2/122 votes | 2%
Everybody Sucks Here (ESH) 0/122 votes | 0%
Need More INFO (INFO) 0/122 votes | 0%

Charles Butler

Charles Butler

Hey there, fellow spotlight seekers! As the PIC of our social issues beat—and a guy who's dived headfirst into journalism and media studies—I'm obsessed with unpacking how we chase thrills, swap stories, and tangle with the big, messy debates of inequality, justice, and resilience, whether on screens or over drinks in a dive bar. Life's an endless, twisty reel, so I love spotlighting its rawest edges in words. Growing up on early internet forums and endless news scrolls, I'm forever blending my inner fact-hoarder with the restless wanderer itching to uncover every hidden corner of the world.

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