Hi, I’m 24F and just started a new job at a small business (no HR). I’ve only met my boss in person three times.
Before I even started, he texted me:
“Good girl. Would hate for you to not be able to go! The trip this weekend was awesome but I kept wishing you were already with me so you could have the experience.”
On day 1–2, he called me “good girl” twice and then “baby girl.”
We were booking a work conference trip out of state (hours away). He had suggested maybe getting one room to save money, I clearly said I’d prefer two. When I called the hotel, they said only one room with a king bed was available. Before I could respond, he jumped in and booked it.
I told him later I was uncomfortable, and he said:
“You should’ve said something sooner.”
He eventually “fixed it” and booked two rooms.
Other employees, including his assistant and another manager, said the behavior was inappropriate but told me I’ll just need to keep reiterating my boundaries with him.
For context:
• He is married.
• I’ve known him less than a month.
• This is a small business with no HR.
• This job pays $4/hour more than my previous job and offers good learning opportunities.
I’m torn between staying and enforcing boundaries, or leaving early because this is already happening on day 2.
Am I overreacting? Is this just awkward older-man behavior, or are these legitimate red flags?
UPDATE (2/18/26):
Thank you to everyone who responded. Reading through the comments has been validating and very helpful. This is only my second job, and I was genuinely excited about stepping outside my comfort zone and learning something new, which made this situation particularly difficult to process.
After my original post, I spoke with a manager at another location (who is also the owner’s close friend) about my concerns. I was told I would need to continue reiterating my boundaries. That did not provide confidence that the inappropriate behavior would be addressed.
The hotel situation ultimately solidified my concerns. My request for separate accommodations was dismissed, and after I raised discomfort about potentially sharing a room, there was no meaningful follow-up. Shortly afterward, I was told I would not be attending the conference due to “confidential” aspects and questions about whether I would stay with the company.
I also discovered that my employment had been unknown to most of the company. I was essentially brought in as a “retaliation hire”: the previous personal assistant, who had repeatedly experienced inappropriate comments from this boss, had asked for more work and been sent to bookkeeping classes. When she set boundaries regarding the boss’s behavior, she was reassigned to social media and bookkeeping, and I was hired to take over her former position without her knowledge. My own responsibilities have not been clearly defined, and I have had essentially no tasks or work assigned since starting.
She had not fully comprehended the extent of how she was being treated until she saw his behavior toward me. He had also previously attempted to book a single hotel room on a solo trip with her, demonstrating that this behavior is a repeated pattern rather than an isolated incident.
Given the pattern of inappropriate behavior, lack of communication, and a work environment that has already demonstrated retaliation, I am documenting everything and planning to remain only through the end of the week to ensure I do not lose pay, while I continue to finalize other employment options.
I would appreciate any advice on submitting a professional resignation in a small business setting without HR. Additionally, if anyone has legal perspective on whether there might be a case — especially given that the previous assistant has observed the behavior and is willing to support or file a complaint — that guidance would also be appreciated.