Meet the Other Phone. Protection built in.

Meet the Other Phone.
Protection built in.

Buy now

Please or to access all these features

Work

Chat with other users about all things related to working life on our Work forum.

My new older boss makes me extremely uncomfortable

8 replies

Jtfrtj · 13/12/2025 15:11

Part of my new role involves managing an account, the customer business is based in another city 3 hours away. On my second week into the job, CEO told me he visits the site weekly and wanted to take me with him, so I could meet everyone. He knew from my CV that I live in the same town as him, so offered to me up in the morning.

He picked me up the following morning as planned. My interactions with him in the office at that point had been limited (he’s very busy and elsewhere a lot of the time) but professional, however he spent the entire 2.5 hour car journey being what I felt was unprofessional, and sending me subliminal messages that he has a dating or sexual interest in me (this is where I’m unsure, and need advice on if I’m reading too much into things) Examples below:

  • As soon as I got into the car, we started talking about the upcoming Christmas period, if we’d finished our Christmas shopping, the usual… He then said he had two grown up daughters and was divorced from their mum. He then said “I am dating on the apps at the moment” then proceeded to tell me how his ex wife hit the menopause and decided she didn’t like him anymore (this happened to all her female friend too, apparently) she tried to rinse him financially for all his assets, that his kids preferred him to her, and she only applied for full custody so she gets more money out of him. He then told me as a man who is “successful financially” (he repeated this many times) he tells all the women he is meeting on dating apps that he will only marry again if there if there is a prenup involved
  • He asked me who I live with, I still live with my family. I am from an immigrant family who are very traditional and religious (he knows this because on my CV he noticed I went to a faith school, one of which he is aware of. I spoke about my education and mentioned in passing that it was importance to my parents to send me to a faith school) He asked me which country my family are from. I told him, to which he replied “Ah interesting, I dated a woman from X, also women from Y and Z” (all neighbouring countries of mine, same culture). Then he said “I actually prefer women from that part of the world, because while they have more expectations on gender roles, they also know what’s expected from them as women and they bring femininity to the table” I believe he was indirectly referencing to me there, as I always wear office dresses, blazer and heels to work. He mentioned my “lovely” outfit and nails when I had got into the car. He also asked me how old I was.
  • He then said that in the dating world, women are quick to label men as being only after “one thing” but what women need to realise is that sex is important to men and they have that urge by nature, just as women by nature have a huge urge to have children. And there needs to be understanding on both sides. At this point I feel extremely uncomfortable and grossed out by him. This is a man old enough to be my father, I am stuck in his car and just want to escape.
  • He relayed several stories of his bad dates which were very uncomplimentary to the women. On one, he pulled up to find her in the car park, she apparently looked heavier and older in person, and said “oh come on am I really suppose to deal with THAT”. (Despite the fact that he is middled aged, overweight and not attractive by any social norms)

When we left for the day and got back into the car he said “Yeah so as I was saying earlier, I’m not opposed to getting married again, so long as there’s a prenup involved” ?! Like it was relevant to the conversation we were having. It was so random. He then tells me that going forward he will assume I will accompany him on these weekly l site visits with him to maintain a good relationship with the customer. I honestly don’t think I can deal with this every week.

If my suspicions are true, that he is using this time in the car to “test the waters” with me so to speak, I will be both disgusted and insulted. He is old enough to be my father and extremely unattractive I felt sick when he referenced sex being important to men, as I could never look at him in that light (I’m not saying that if he was attractive, it would make it any less inappropriate)

More importantly, if that is the case I will be angry that he is using his power to put me in situations that I can’t escape. There’s no option for me to drive there, the company will only reimburse one vehicles mileage. I have no idea how to handle this, as he is the CEO he is the highest rank, and HR are ultimately there to protect the business not the employee.

OP posts:
cordeliavorkosigan · 13/12/2025 15:18

Gross. And for 3 hours.
I hope people with better advice will come along soon. But telling him you prefer not to discuss dating or personal lives might help.
Obviously try to get out of going every time? Do you have a line manager who could really really need you to do other work at those times, so he would feel some pressure not to bring you?
If that all fails maybe say you really must listen to x podcast and have headphones in.
I imagine if his advances don't land well he'll get bored of bringing you...
But that sounds awful! So sorry you're going through it.

KentishMama · 13/12/2025 15:18

The company can reimburse two vehicles' mileage, in particular as one of them is the CEO's.

Option 1: You address it with him directly. "I'm so sorry, but I have to say I felt quite weird about all the dating stories you told me. We will be driving together more often, so can we perhaps agree that we keep to more professional topics?"

Option 2: Is there an HR function? Can you tell them some sort of story that your family has major objections to you being alone in the car with an older man every week, for religious or cultural reasons, or something?

This is tricky, and I feel for you.

Jtfrtj · 13/12/2025 15:20

cordeliavorkosigan · 13/12/2025 15:18

Gross. And for 3 hours.
I hope people with better advice will come along soon. But telling him you prefer not to discuss dating or personal lives might help.
Obviously try to get out of going every time? Do you have a line manager who could really really need you to do other work at those times, so he would feel some pressure not to bring you?
If that all fails maybe say you really must listen to x podcast and have headphones in.
I imagine if his advances don't land well he'll get bored of bringing you...
But that sounds awful! So sorry you're going through it.

Thank you.

Unfortunately I don’t have a line manager to speak to, I report directly to him. This is why I don’t know how to handle it.

OP posts:
Jtfrtj · 13/12/2025 15:27

KentishMama · 13/12/2025 15:18

The company can reimburse two vehicles' mileage, in particular as one of them is the CEO's.

Option 1: You address it with him directly. "I'm so sorry, but I have to say I felt quite weird about all the dating stories you told me. We will be driving together more often, so can we perhaps agree that we keep to more professional topics?"

Option 2: Is there an HR function? Can you tell them some sort of story that your family has major objections to you being alone in the car with an older man every week, for religious or cultural reasons, or something?

This is tricky, and I feel for you.

Option 1: You address it with him directly. "I'm so sorry, but I have to say I felt quite weird about all the dating stories you told me. We will be driving together more often, so can we perhaps agree that we keep to more professional topics?"

This is probably the most logical solution however I think he’ll wonder why I didn’t say this the first time. I didn’t throughly engage with the conversation, he spoke 90% of the time. My main responses were “mmm”, “I see”, “sounds tough”. A couple of times I didn’t respond, to which he just laughed awkwardly and said “Anyway..” let continued to talk on the topic.

The truth is I was so taken aback, and two weeks into a new job I was excited about, I wanted to make a good. I thought the conversations would end soon enough but he didn’t discuss work once the entire journeys. It wasn’t until the next day I felt so uneasy. I really can’t stand the thought of it every week.

OP posts:
PurpleDisco · 13/12/2025 18:39

@Jtfrtj he sounds like a creep. Being as he’s the CEO there is no other option here but to start looking for another job now. You sound astute so you’ll more than likely be offered another position soon.

It’s not appropriate for you to be trapped for 5 hours in a car with a dirty creep every week. I don’t recommend confronting him / asking for conversations to be professional either as that could make the situation worse. Even if he seemed ok at first you simply don’t know how he could react once you’re in the car with him. Do not put yourself in danger.

He’s a bully and is using his power to think he can get what he wants with you.

Be strong, no job is worth risking your safety for.

Trabbling · 13/12/2025 18:51

That sounds truly awful. Maybe email him saying you didn't know what to say at the time, but having thought about it and discussed it with a few people (ie. us!) you need to say that the conversations about dating, sex, his previous relationships, etc. made you really uncomfortable and you would rather stay away from such personal conversations in future. I'm suggesting emailing so that you have his topics of conversation, and your request, there in b&w.

Apparentlyitschristmas · 13/12/2025 18:53

I also think you need to start looking for a new job - something similar happened to me when I was young and ultimately I was made redundant . I was so repulsed and naive I think my disgust was all over my face .

In the mean time tell your family , and consider creating a fictitious serious relationship whilst you plot another option .

Im sorry OP - it shouldn’t be like this , but he’s clearly a creep

Jtfrtj · 21/01/2026 16:10

Hi all.

Just to update; I handed my notice in. I felt far too uncomfortable around CEO after the car encounter. As mentioned in my previous post, he told me “Going forward, every week when I travel to the other office I will just assume that you will come with me. I’ve got a meeting next Tuesday so I’ll pick you up again”. There is no business need for me to be there, I am entry level and nobody is reporting to me. I am more than capable of doing my role in our usual office.
The following Monday at 4pm I made up an excuse as to why I could not go with him the following morning (his meeting in the other city was still going ahead at that point). But I came into our usual office the next morning, and he was there. When I mentioned in passing “Oh you didn’t go to other city then?” He vaguely said “No I didn’t go in the end”…

The inappropriate comments continued, far too many to write on here (they were not all sleazy or directed to me). For example when an Asian colleague of mine walked out the room for a moment, he whispered to me “I should have warned you, he doesn’t like wearing deodorant” and laughed. Towards the end of the day he brought it up again, then added “Not wearing deodorant seems to be common in the Asian community” He also referred to this colleague as “Not autistic but acts a bit autistic-y. He means well though”.
I also caught him on a few occasions watching me walk through the office and smiling at me from his office (the looks did not appear to be platonic) I avoided him entirely after that. Did not make any eye contact with him, went out of my way to avoid any conversation with him. Eventually he picked up on this, when I had to approach him eventually he said in private “I thought you had fallen out with me. I’ve been thinking; did I offend her on the drive to the other office? Admittedly I do overshare a lot”

Shortly after that conversation I spoke to my Head of Department to inform him I was leaving, and why. For context; this man also reports to CEO, I work very closely with him and have a good working relationship with him. He was the one who’d recommended me for the job. We know people in common from previous companies as it’s a small industry. Due to this I felt I was letting him down in some way by quitting the role so soon, and didn’t want my name tarnished in the industry for future opportunities.
At the start of the conversation I made it clear first of all that I was speaking to him off the record, I was not expecting him to do anything (due to the dynamics of CEO being his boss it’s not possible anyway) I just wanted him to understand my reasonings for leaving him in the lurch so to speak…

Honestly, I wish I had not bothered as some of his responses left me feeling more annoyed about the situation than I was before. I told him everything I’d mentioned on here and more, that I feel extremely uncomfortable around CEO, he lacks professional boundaries. I said that I felt he’d spent the entire 5 hours in the car that day indirectly letting me know he was interested and available, hinting to me I was what he is usually attracted to, paying compliments and going out of his way to find things we have in common. I started to cry as I felt embarrassed having the conversation, and extremely awkward. Head of Department (HoD) responded “Well I could say this and that to you but it doesn’t mean I’m interested”. He then said “I don’t know what to say maybe he’s nervous, maybe he was just having banter”. I then firmly told him it wasn’t banter at all, that I was only in his car for 10 minutes before he started randomly telling me about his online dating experiences and adding that “Women are quick to label men as only being after sex, but what women need to realise is men have strong biological urges for sex the same way women have strong urges to have babies. If we take that into consideration they need to consider our needs, and realise that’s how we express care and love”. HoD’s response to that was “Well again I can’t comment on that as I don’t know what sort of conversations you’ve been having with him”. I was offended as I felt he was implying that I had previously been ‘bantering’ about topics of a similar nature and I had encouraged him to say such things to me.

HoD also noticed my phone on the table next to me and said “You’re not recording this are you??” This added to my annoyance and I reminded him that I was speaking to him off the record out of curiosity because I’d felt I was letting him down by handing in my notice so soon. I was not looking to make a fuss over anything and wanted to depart the business quietly. It ended with HoD saying “Okay so just to confirm he’s not actually done anything then? It’s just conversation?”…

He gave me no credit for my situational awareness, if a somebody is testing the waters with me on a non-platonic level, then I see through it. I’m not stupid. He was speaking to me from what felt like a legal textbook, despite the fact I’d made it clear I had no agenda by speaking with him.

OP posts:
New posts on this thread. Refresh page
Swipe left for the next trending thread