I (F,26) recently started talking to one of the executives at my work. He (M,52) has been incredibly friendly from one day which then turned to flirting daily. Eventually I asked him for his number to talk about cars (I’m getting a new one and it was my excuse to get his number.) He gave me his business card and immediately answered when I first reached out.

Since then we’ve texted briefly and spent an hour on the phone talking. I needed advice on a work situation and he was really helpful. During that conversation, he suggested we go out. I agreed and eventually he told me he wanted to show me his second house (it’s on a beach). I agreed but we didn’t set a time or anything. Well I called him Saturday night to make plans and he asked if I wanted to come by when he finished dinner with his friends. I declined and suggested Sunday to which he seemed happy about. The call was going in and out due to service but he said he’d call me when he was done. On the call he also asked if I wanted to know the code to his house so I could meet him there. Two minutes later, he sent me his address. Well, he never ended up calling me back or anything. I thought we were set to make plans and am so confused that he just sent me his address and nothing else.

Then today, he completely avoided my office and left early for whatever reason. He normally talks to me everyday and goes out of his way to see me. Did I do something wrong or did he think we were going to hook up and now doesn’t care? I’m worried I might have rejected him in his eyes and it may just be a miscommunication. Advice appreciated thanks.

TL;DR- I caught feelings for my boss and he’s since pushed back. I don’t know if it was something I did or he truly only wanted to hook up. Thanks.

11 comments
  1. You realize he’d 300% get fired if any part of your story came to light, right? His flirting is wild sexual harassment, and it’s irrelevant if you are into it as it’s creating a hostile workplace for others and creates the illusion that a younger employee could advance by having a relationship with an executive

    Outside of the professional sphere, is he single? Does he have a wife who may have picked up on this?

  2. Maybe he realized he’d be stupid as fuck to do something like this. Leave this dude alone. It sounds like you are 100% trying to cause drama for yourself and your boss.

  3. You’re missing the fact that you should not have pursued him in the first place and he’s an absolute moron at best and a creep at worst for even considering this. He’s an executive at your company and fully *double your age*. Fun to fantasize about, maybe, but in real life? A disaster waiting to happen.

    I wouldn’t be surprised if he told his friends about the young woman he was making plans with and one or more of them told him what a bad idea it was.

  4. I don’t even know how you’d think this is more complicated than it is? Trying to be empathetic here, but… sis, the simplest answer is the most likely.

    You don’t shit where you eat, and that exec had a major lapse in judgement. He probably realized it was a stupid, stupid, STUPID idea to throw away decades of work over this. Or, like the other commenter said; he lost interest because the chase was more fun.

    From one woman to another: I’m not sure why you’d want to throw away your professional reputation over a creep who was probably having a midlife crisis.

  5. Dont dip in the company ink, unless of course you dont want to work there anymore

  6. Yeah no. Sorry, hard pass on dating any coworkers. It never ends up well unless one of you is willing to quit.

  7. Date someone your own age. Why do you need to date someone your father’s age? Can you please grow up, the only people in their 20’s who want to date men in their 50’s is all about money money money. What are you going to talk about? How you both grew up back in the day struggling? I don’t think so. You most likely have nothing in common outside of cars.

    You are creepy as sin.

  8. I would say he told his friends about it at dinner and they mentioned it was a bad idea, so he cut communication cold turkey, idk tho.

  9. I think it’s possible he realized that he’s overstepping some boundaries.

    When he texted you the address and you didn’t text back, he probably thought you weren’t interested and then he panicked. He realized that this was stepping over the boundaries

    But since you are interested then just inform him that you thought he was going to touch base with you about when to come over on Sunday and since he didn’t you just wanted to see about another time

    There’s definitely cases where miscommunications happen so give that a try and see if you can still meet up with him

  10. Lol. You know this is a bad idea because you called him your “coworker” in your header, but went on to call him an Executive at the company and then called him your boss. Even your story went from bad to worse.

    Don’t date a higher up in your own company, especially if you are their direct report. THere are plenty of older men looking for 26 year olds to hang on their every word. Find one of them that you don’t rely on for a paycheck.

  11. Ignoring the age gap and workplace issues, I’m guessing he thinks you stood him up. Maybe to your generation its okay to start plans and bail, but to the rest of us that would be ghosting and a clear indication that we aren’t a priority or you aren’t interested. You tentatively made plans and didn’t follow through. If you want to fix it you message him and say something like-

    Hope you had a good weekend. We never got to finalize our plans. I’d love to see that house.

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