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Single Mom Tells Boss To Stop Sneaking Into Her Driveway, Was She Too Harsh?

by Annie Nguyen
November 15, 2025
in Social Issues

Workplace dynamics can sometimes blur the lines between professional and personal, especially when a boss starts acting in ways that feel off. For single parents, maintaining clear boundaries is even more crucial to protect their home as a safe space for their kids.

The original poster (OP), a single mom with a teenage daughter, has been at her marketing job for six months. Lately, her boss has been showing up at her house uninvited for “work chats,” a practice she’s learned he doesn’t do with other coworkers.

After an uncomfortable moment when she spotted his car in her driveway, she confronted him, but his response left her second-guessing herself. Scroll down to see how this unsettling situation unfolded and what advice the internet had for her!

One woman is rattled after spotting her boss’s car lurking in her driveway, stirring up unease as her motherly instincts kick in

Single Mom Tells Boss To Stop Sneaking Into Her Driveway, Was She Too Harsh?
Not the actual photo

AITAH for telling my boss I am not comfortable with him randomly visiting my house?

I am mid 30s, single mom of an 14 yo daughter. With our two dogs, we are the only ones that live here.

I work in marketing and at this exact place for 6 months. My boss is in his early 40s presumably but I don't know his exact age.

He might not be married because he doesn't wear a ring but I don't know for sure.

Recently my boss has been acting strange towards me.

He doesn't want to talk to me at work anymore and prefers to come over to my house during the evenings and chat.

I was fine with this the first couples of times but i'm starting to feel uncomfortable about it

because my other coworkers told me he doesn't do it this way for them.

Last night I saw his car parks at the front of my driveway and then he called me and asked if I wanted to talk tonight, I said no and...

I called him back this morning (I'm on vacation until Monday because july the 4th)

and asked him to stop doing meetings this way because it's creepy and i'm not comfortable with doing it this anymore.

He told me it's however he generally does it (remember what I said when my other coworkers don't have meetings with him at their houses). I felt uncomfortable.

I decided to text a coworker I am friends with and ask her if I did anything wrong by telling him to stop and she said I am acting like...

Now I think maybe I am over reacting at all of this and should just let him visit for meetings.

Most people know that home is the center of our emotional safety, a place meant to protect our peace rather than challenge it. When someone crosses into that space uninvited, especially a person with power over our livelihood, it creates a kind of emotional dissonance that’s hard to shake.

In this story, OP isn’t just reacting to a manager’s unconventional habit; she’s managing fear, uncertainty, and the instinct to protect her daughter and her own peace. That mix of confusion and discomfort is something most people can relate to, even if they’ve never experienced this exact situation.

From a psychological standpoint, OP’s unease is rooted in a very normal boundary response. The boss’s behavior violates the implicit social contract between employees and supervisors, professional distance, predictability, and respect for privacy.

OP didn’t feel hurt simply because he showed up; she felt threatened by the unpredictability, the singling-out, and the fact that his actions differed from what he did with other employees.

People rely heavily on social comparison to interpret whether a situation is safe or dangerous. The fact that no one else received home visits immediately signaled to OP that something was off, triggering discomfort and vigilance.

While most readers focused on the obvious creepiness, there’s another angle worth considering: some people, especially those conditioned to “be agreeable,” tend to downplay early red flags to avoid conflict.

Where others see danger, OP initially saw awkwardness. It’s a common psychological response, particularly among women, to prioritize harmony over confrontation, even at personal discomfort.

Dr. Deborah Tannen, a sociolinguist known for her work on workplace communication, explains that power dynamics can distort how people interpret boundaries.

When someone in authority behaves inappropriately, subordinates often hesitate to judge the situation clearly because they fear misinterpreting the intent or facing retaliation.

Similarly, researchers on boundary violations note that people often “freeze” rather than react when they sense a potential threat, especially when that threat comes from someone they rely on professionally.

Verywell Mind also highlights that feeling pressured to be polite can override our instincts to protect ourselves.

This insight reveals why OP’s discomfort isn’t paranoia; it’s a correctly calibrated response to an authority figure blurring lines.

The expert perspective reinforces that her boundary-setting wasn’t an overreaction but appropriate self-protection. It also underscores why documenting, reporting, and insisting on professional norms are critical steps in situations involving power imbalance.

Ultimately, this story invites a broader reflection: trust your instincts, especially when someone who should respect your boundaries begins to test them. Even small acts of discomfort often point to much larger truths.

Take a look at the comments from fellow users:

These Redditors backed her boundary-setting and urged HR action

MistressJacklynHyde − NTA. He is crossing boundaries. You are there to work for him.

He should ONLY be discussing work with you AT work. He is waving so many red flags!

Does your company have an HR department you can go to? What he is doing is completely unacceptable!

greenwitheverything − Why would he ever come to your house for a meeting? It was inappropriate every time,

not just now that you're uncomfortable.

I would make a formal record with HR.

He also needs to be told to not text or call after work hours as well.

[Reddit User] − NTA. Take this to HR. This is not normal or acceptable behavior.

BoopityGoopity − Make a record of all the times he's come by. A brief description of each occurrence if possible.

Plus note that you've spoken with other coworkers.

Go to HR with a printout of this record and your laptop so you can also email them the file

for a digital copy as you're in the office with them.

Make sure you CC/BCC an external email address as well so they can't wipe it completely

(in case your boss has an in with an unethical person in IT). This is the only way it stops.

BubblyBubbles1007 − You are not the a__hole. This is 100% unprofessional.

If he has to meet with you, it should be during work hours only.

I'm just getting creepy vibes from this guy

2dogslife − What he's doing is a gross overstep. I have had after-work meets (or even lunches) with bosses,

but they were always at some neutral location like a coffee shop, restaurant, or bar, and often times included other coworkers.

I have never had a boss at my house. I've had coworkers drop me off when previously arranged because of car problems,

but I have always held firm lines between work and my private life.

It's no longer midcentury when wives stayed home and husbands invited their boss and his wife to dinner.

His behavior is disturbing. I don't know if he wants to date you, but it doesn't sound mutual at all.

Contact HR, they can manage his behavior and expectations. It's s__ual harassment to my thinking.

New-Waltz-2854 − As a former manager I can tell you this is 100% inappropriate.

I never, ever would stop by an employee's home unless I was invited and other people would be there.

You need to tell him to tell him to stop and that if he persists, you will call the police.

You can also report him to HR. But you do need to make it very clear that he is not welcome at your home.

It is difficult for HR or law enforcement to do anything if you do not tell him no.

forgetregret1day − NO NO NO NO NO. This is not okay. Please report this to your HR department immediately.

Your coworker is an i__ot for not telling you that exact same thing and being genuinely concerned for your wellbeing.

Work discussions happen at work, not in the home of an employee, much less a male manager in the home

of a mom and her young daughter. This is 1000 kinds of wrong.

He is in a position of authority over you and acting like a creepy stalker in the name of the company-

an important point to make to HR. Please immediately report this and be careful.

Do not engage with him at your home except to tell him to leave. Keep your phone with you

and call 911 if he becomes aggressive in any way or says he'll just come in for a minute or whatever.

The answer is no. I'm so sorry this is happening to you. NTA.

Georgeyboy70 − Huge red flag, putting aside any ulterior motive he might have for coming to your house,

when you're at home you're off the clock so he should not be contacting you for work purposes.

You are well within your rights to say 'no' to speaking to him, tell him you will discuss whatever needs to be discussed when you're in work next.

Downtown_Area111 − NTA. Tell him that you will do your meetings at work.

Once you clock out, you do not discuss work.

Please do that via Email or text so you have a paper trail.

That way if he retaliates against you, take it up with HR!

kcvaliant − Umm no. Nta. Huge red. flag of him overstepping. Tell him no everytime.

Record that none of the other co workers have had this happen.

Ask a lawyer what you should do next if he dosent. stop.

Dublinclaudia − Creepy. Never had a boss want to come over. EVER. That is crossing a boundary. Creepy

booksdogstravel − NTA. Your coworker is a pill. Stop confiding in her.

If he requests another meeting with you at home, send him an email saying you would rather do it at the office.

If he doesn't respond appropriately, and stop doing this, escalate things to HR. But you need documentation. I find him creepy.

susannahstar2000 − It's borderline stalking. I would call the police the next time he is parked outside your house.

This user cheered her stance but pushed for legal advice and documentation

Creative_Carrot_7514 − You are misunderstanding your friend. You are acting like a c__ard by not setting clear boundaries

and explaining why you are not comfortable with this.

Are you Salary and are you in the US? Because if you are in the US and hourly this could be a clear violation

of certain laws and union agreements. I would speak directly with HR, explain why you are concerned

and don't feel safe, and that you are being put in a uncomfortable position and are documenting things as they come up.

Now, start documenting everything he has done so far, find the proof you can find on it, texts, etc,

and call a labor law attorney.

This mom’s standoff with her boss is a wild ride of courage and confusion. Did she nail it by shutting down those driveway drop-ins, or did she overstep with her firm “no”? The lifelong stakes of safety and respect hang in the balance, especially with a teen and pups in tow. How would you handle a boss who can’t read the room? Share your hot takes below, let’s spill the tea on balancing work weirdness with home sweet home!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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