I put up some boundaries since he rejected me. We strictly work together and don't go out as friends. I desperately miss our friendship, and I would love to have that back.
I almost talked to him about wanting to renew our friendship, but then I realized he is dating someone. And it hurt to hear that. Because truthfully, I am still holding on to hope. And I am incredibly angry at him for giving me hope. Had he simply rejected me and not held my hand while he told me that he has questioned his feelings for me, I probably would have moved on. But here I am, a 40-plus-year-old women with a crush on my boss.
How do I move past this? Can I ever be his friend? I've looked for other jobs, but I love my work.
— Holding On
Holding On: You can never be his friend.
Your feelings will not be returned.
If you want a romantic partner in your life, then you will need to look for one in someone other than this man.
A no with a flicker of “maybe” in it is just as much of a no as a simple rejection.
I am sorry for all of this. It is obviously way more nuanced than these four statements say it is, certainly for you and maybe even for him, but nuance that brings you nothing is not worth exploring. The face of it is all you need to see: No, you can’t; no, they won’t; he’s not the guy.
And possibly most important: If your feelings were mutual, then you two probably would have found a way to be together.
Keep loving your work, keep looking for work elsewhere, stomp on every ember of “what if,” and keep reminding yourself that the problem isn’t that he is your boss, it’s that he’s not the guy.
Re: Holding On: If he's not the company owner, then he may have more exposure in terms of company policy violation, sexual harassment charges, etc. He may be mindful of all of this. If you want to test this theory, leave for another job. If he reaches out to you then, there may be some romantic future for you two. In any case, leaving may be what you need to move on emotionally.
Re: Holding On: Her phrasing shows she is putting the blame on him, and it's true that he should have been more careful about getting so close to a subordinate, but she has a lot of stuff she needs to own. Maybe working to try to own it will help in processing the pain. Any relationship is a gamble, and much more so in the workplace.
— Own It