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My new older boss makes me extremely uncomfortable

36 replies

Jtfrtj · 13/12/2025 16:18

I don’t know what to do or if this is even resolvable at this point

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 said he’d pick me up from my home 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 3 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:
bevelino · 13/12/2025 17:07

slughater · 13/12/2025 16:57

pick your nose in the car
tell him your parents are choosing a husband for you
record his conversations on your phone and keep all texts and emails
tell him you can manage the visit alone
tell him you have genital herpes

Please don’t say you have genital herpes. That’s not something to joke about or mention to anyone at work.

Ritaskitchen · 13/12/2025 17:05

His conversation was wildly inappropriate. Im sorry. I would avoid to be alone in a car with him again. You could say your parents don’t like it.
I would be polite but distant and keep it professional. "I don’t discuss personal matters at work, change subject“

AltitudeCheck · 13/12/2025 17:05

Mention his age in conversation... What should I get my dad/ grandfather for Xmas, he's about your age?

I came off the apps, I kept getting hit on by men old enough to be my father, gross!

I wouldn't date an older man / divorceee/ someone who doesn't share my faith / believes in old fashioned gender roles/ is a misogynist.

Do you have children? Oh they must be about my age... is your son single?

Nugg · 13/12/2025 17:03

Hoardasurass · 13/12/2025 16:56

Please have a conversation with HR about his massively inappropriate topics of conversation and his sexual harassment of you.
He's a disgusting misogynistic twat whos a walking red flag with the way he talks about his ex wife and women from your culture and the needs of men for sex and a woman's responsibility to provide it at comand

This!! Why would you even entertain it go straight to HR!!

InterestedDad37 · 13/12/2025 17:01

Sounds like a total creep 😕

Jtfrtj · 13/12/2025 17:00

Hoardasurass · 13/12/2025 16:56

Please have a conversation with HR about his massively inappropriate topics of conversation and his sexual harassment of you.
He's a disgusting misogynistic twat whos a walking red flag with the way he talks about his ex wife and women from your culture and the needs of men for sex and a woman's responsibility to provide it at comand

Honestly I was amazed he managed to tick every “Things you must not say in the workplace in 2025” box. He lacks so much self awareness for a man of his age and work experience.

If he was ‘just’ a manager I’d have gone to HR by now but he’s the CEO there’s no one above him. I don’t have a leg to stand on do I.

OP posts:
slughater · 13/12/2025 16:57

pick your nose in the car
tell him your parents are choosing a husband for you
record his conversations on your phone and keep all texts and emails
tell him you can manage the visit alone
tell him you have genital herpes

Jtfrtj · 13/12/2025 16:56

ThatLemonBear · 13/12/2025 16:45

Can you invent a boyfriend (or girlfriend) and tell him you’re in a relationship now? You shouldn’t have to do this, but if you can’t avoid the car shares and don’t think HR will help, that might make him back off at least

Unfortunately he knows I’m single 🙄 I think even if he was under the assumption I’d started to date someone, I don’t think that would stop him. He’s actively going on dates through the dating apps himself.

I forgot to add in the OP- another thing he kept saying in the car was how as a man of his “financial success” the next woman he dates needs to be ambitious… while strategically finding a way to reference my plans to undertake another high level qualification shortly afterwards. (We’ve previously talked in details about my career plans for the future too) Everytime he did it I felt like rolling my eyes. I get the impression he thinks he’s being a lot more subtle than he actually is and he’s successfully putting thoughts in my head. It feels almost manipulative in a way.

I’ve also caught him watching me walk through the office a few times.

OP posts:
Hoardasurass · 13/12/2025 16:56

Please have a conversation with HR about his massively inappropriate topics of conversation and his sexual harassment of you.
He's a disgusting misogynistic twat whos a walking red flag with the way he talks about his ex wife and women from your culture and the needs of men for sex and a woman's responsibility to provide it at comand

Redpeach · 13/12/2025 16:48

What an absolute cock, his poor ex wife

ThatLemonBear · 13/12/2025 16:45

Can you invent a boyfriend (or girlfriend) and tell him you’re in a relationship now? You shouldn’t have to do this, but if you can’t avoid the car shares and don’t think HR will help, that might make him back off at least

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