July 29, 2026 at 6:15 am

“He Said It Was a Compliment”: Employee Torn Over Supervisor’s Uncomfortable Behavior

by Jayne Elliott

older woman talking to younger woman at work

Shutterstock

Imagine traveling with your boss and coworkers for business. What would you do if you thought your boss’s comments and actions were a bit creepy? Would you brush them off and assume you’re overreacting, or would you tell HR and keep your distance?

In this story, one woman is in this situation, and she’s not sure if she’s overreacting or not. She provides several examples of things her boss has said and done that made her feel uncomfortable, and after reading these examples, I’m positive her boss is a creep!

Keep reading to see if you agree.

AIO to my boss/supervisor’s comments?

I (30sF) work in a creative field that requires time on the road.

As such, my colleagues and I are not always on the clock while ‘at work.’

We have dinner, grab a drink/coffee, go to parks etc.

I have been working in a support role with this group for about a year.

Her boss is making her feel uncomfortable.

Recently, my boss (50sF) has started pushing boundaries with me: asking to room together each night rather than rotating roommates when we change hotels, putting her hand on my leg when we talk, etc.

We have been friendly in the past, and she has been very supportive of me and my career.

We have talked about some difficult things we’ve each been through (medical issues, family politics, etc), and it felt like we were mentor/mentee.

I understand she has had a tough go of things lately (haven’t we all?) and may need some additional support, and I appreciate everything she has done for me, but I am reaching a point where I am uncomfortable.

Wow! This is a very inappropriate thing to ask!

Last time we worked together, she asked me if I was wearing underwear.

This was in a public place (I contained my reaction), and in front of other (male) colleagues.

I laughed it off in the moment so I could do my job, but now I’m feeling like that is just the tip of the iceberg. AIO?

No, she’s not overreacting. Her boss is being creepy, inappropriate and unprofessional. She needs to report her to HR immediately and keep her distance.

Let’s see if Reddit agrees.

This person doesn’t think she’s overreacting at all.

2026 07 28 at 10.07.21 AM He Said It Was a Compliment: Employee Torn Over Supervisors Uncomfortable Behavior

If you enjoyed this story, check out this post about an employee who totally rearranges her schedule, only to have her boss change plans last minute.

One person offers a suggestion of what to say about the roommate situation.

2026 07 28 at 10.07.47 AM He Said It Was a Compliment: Employee Torn Over Supervisors Uncomfortable Behavior

Another person offers advice on how to talk to her about the underwear comment.

2026 07 28 at 10.08.16 AM He Said It Was a Compliment: Employee Torn Over Supervisors Uncomfortable Behavior

Her boss is definitely creepy. If her company has HR, she should talk to them immediately. If not, it might be time to look for another job. I wouldn’t feel comfortable traveling with this woman let alone sharing a hotel room with her.

Enjoyed this story?

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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.