June 14, 2026 at 7:55 pm

Woman’s Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

by Jayne Elliott

two businesswomen talking

Shutterstock

Imagine having a relationship with your boss where you don’t just work together but you’re kind of friends and talk about personal issues, such as relationships. Would you be upset if your boss gave you unsolicited dating advice after overhearing you talk on the phone with your boyfriend, or would you be happy to listen to her perspective?

In this story, one woman was in this exact situation, and she’s really annoyed with her boss. Not only did she give unwelcome advice, but she also brought up a traumatic situation that occurred in the past.

Eventually, she stood up for herself and shut down her boss’s comments, but she feels bad about it. Did she go too far? I don’t think so, but keep reading to see if you agree.

AITA for setting a firm boundary, ticking off my supervisor?

I work at a very chill business, and my direct boss and I are friendly.

I’ve been with my current bf about 5 months but we were best friends for over a year before we decided to be together.

We met on Facebook dating went on a date and decided to be friends and became best friends.

We’re talking about the serious topics like marriage and kids as in we want them in a few years not next week. I’m 23f he’s 25m.

The boss overheard her talking on the phone.

My boss overheard a phone call on my break when I was in the other room where we were talking about the people I live with not being the best and threatening to kick me out for working so much and not being home more than nights really.

So he offered to let me stay with him if that happens, and I said “if they do end up doing that I’ll stay with you but i also have rooms with grandparents and a best friend I can stay with. Plus I want to wait to live together.”

They say 20 minutes later “you should never have those conversations until you’ve been dating at least 4 years.” And then asks if we’ve talked about marriage and kids.

I said yes because it’s a deal breaker with differences in choices on those topics and we had those talks when we were best friends in a friendly way and we sat down and intentionally made sure we were on the same page 3 weeks ago to make sure we were compatible. And left it at that.

The boss brought it up again.

2 days later they pull me over and say that “so and so didn’t even do this until 6 years in” or “so and so didn’t even do this until 3 years in”.

I just look at them like “what..?”

I told her not everyone shares their ideals and I respect that they care enough to say something and appreciate it very much however me and my boyfriend F are on a path that is intentional and will go at the pace that suits us.

They said “well the last one you moved way too fast. I don’t believe the last guy was as bad as you made him out to be so what’s to say it won’t happen again”

Here’s some context about her ex.

This hurt, last year I had a severe DV relationship with my ex fiancé and it ended in him cheating for 2 months with someone twice his age while I was pregnant and led to a miscarriage.

I do not like people comparing my current relationship with T to this one.

I currently have charges being pressed on my ex fiancé but he jumped the state to avoid them.

I do not stand for them comparing the amazing man I’m with now to that horrible person.

She finally had enough.

I told them to stop firmly and I will not entertain condescending words or bringing up past trauma.

Now they are acting extremely cold and saying “I just wanted to help” in a condescending way.

I’m a people pleaser and know I should have shut that conversation down right away.

AITA for setting that boundary firmly? I feel horrible that I may have upset them by being firm about it but I’m genuinely just not sure.

Five months isn’t very long to be dating someone, but what is the boss talking about with four years and six years? A lot of people get married in much less time than that. And the boss was completely out of line bringing up her past trauma.

If you enjoyed this story, check out this post about a professor who missed a major funding deadline after they told their graduate student to leave them alone.

Let’s see how Reddit responded to this story.

This person is on her side.

2026 06 13 at 3.35.42 PM Womans Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

Another person thinks the boss should’ve minded her own business.

2026 06 13 at 3.35.53 PM Womans Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

Here’s a suggestion of what to learn from this experience.

2026 06 13 at 3.36.15 PM Womans Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

Another person suggests not having personal conversations at work.

2026 06 13 at 3.36.56 PM Womans Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

One person shares an experience with her own boss.

2026 06 13 at 3.36.45 PM Womans Boss Listened In on Her Phone Call With Her Boyfriend — Then Gave Her Unsolicited Relationship Advice

Her boss should’ve stayed out of it. However, she also should’ve waited and had that conversation with her boyfriend some other time, like when she wasn’t at work, possibly in person. I get that she felt the need to vent, but it wasn’t the time or the place.

Her boss was only trying to help, but nobody likes unsolicited advice. Also, I’m weirded out by the boss’s suggestions. How long does she think you need to date someone before knowing this relationship is solid? Throwing numbers like four years and six years around means you’d probably never date long enough in her opinion to actually ever get married.

If you enjoyed this story, check out this post about an employee who wasn’t keen on contributing more to a coworker’s gift than originally planned.

Jayne Elliott | Contributing Writer, Life & Drama

Jayne Elliott is a contributing writer and editor for TwistedSifter specializing in human interest stories, internet culture, and family dynamics. With over 12 years of editorial experience in digital publishing, Jayne excels at analyzing complex online communities and transforming viral social debates into thoughtful, highly engaging narratives.

Rather than simply aggregating internet drama, Jayne brings a sharp, empathetic editorial eye to everyday dilemmas. She has a unique talent for unpacking the nuances of pop culture and online conflicts, providing readers with relatable, well-researched commentary.

Based in California, Jayne spends her free time outside the newsroom exploring theme parks with her family or beach-combing along the coast.

Follow Jayne's adventures and connect with her on Instagram, Facebook, and YouTube.