How To Find Out If My Boss Shares My Feelings

Question to Ask the Workplace Doctors about more than friends: We were the ones who practically started the company operations. However, as days have passed, we are becoming closer. I’m a bit afraid of that.

My boss and I are good friends. Perhaps, it’s because we were the ones who practically started the company operations. However, as days have passed, we are becoming closer. I’m a bit afraid of that.We sometimes have lunch together, share foods, and talk about personal things over a dinner. I am like the only person he trusts with regards to company properties and all that. I do overtime because of workloads, with me and him alone in the office.

I would like to reiterate that we are close, but I was terrified upon seeing him in my dreams on consecutive days. The dream would always portray everybody in the office hating him but I was the only one saving him.Plus, there were instances in my dreams that we were engaged in a personal relationships but hiding it. Last night I was terrified upon dreaming of him being so sweet that he had given me this hug and kiss. This time, he lets our guard see it. That was terrible and I am bothered because we are seeing each other every day.I would like to know if he is having the same things happen without him knowing that I am trying to find out.

Signed, Dreaming

Dear Dreaming:

It’s not uncommon to dream about people you’re interacting with a lot, especially if you share a strong bond as you and your boss seem to do. Some people have told me they have had very sexual dreams about people they work with who they dislike very much and find very unattractive. So, dreams are not necessarily indicators of anything except brain activity.However, in this case it does sound as though you are infatuated with your boss a bit and would like it if he was infatuated with you as well, so you’d like to know if he is having romantic dreams about the two of you

.Before you get into a situation that is awkward and may create problems for both of you, consider a few important things:

1. If your boss finds out you are having personal thoughts about him and he says he is having similar thoughts about you, what then? Is he married? Are you? Would you be able to keep working there? Would you be able to be open about it? What would it do to the business? If he says he does not have personal or romantic thoughts or dreams about you, what then? Will that make your work awkward? Will he stop talking to you so much? Is that going to be effective for getting work done?

2. You mention that you and he practically started the company and that you work overtime, have dinner together, etc. Surely he realizes the impression this gives everyone. If there are other employees in the company, they probably think you two are involved anyway and resent the closeness. Is that a good thing for him and you and the company? You can answer those questions better than anyone else, because you know him and the situation best. I just want you to avoid doing something that will get a shocked reaction from him and perhaps create problems for both of you. If, after all of that, you would like to know if he is dreaming of you and him and work, you could ask your question, but not refer to the nature of your dreams. Instead, make a statement like, “Wow, my head was so busy with thoughts about work I dreamed about work all night long! Have you ever done that?”Or, you might say, “I think we’re working too hard. Last night I dreamed about us working and trying to overcome all kinds of problems. I felt like I did a double shift! Do you ever do that?” Keep your tone light and humorous rather than asking in a coy or personal sounding way. Asking in those ways keeps it from sounding as though you had a personal or romantic dream and instead just dreamed about work.If he wants a romantic relationship with you, he might ask you if you dreamed about him. That’s when you need to know in advance if a romantic relationship is something that is a possibility or would you ruin his marriage or yours or your working relationship. If he isn’t interested in a romantic relationship he might talk about dreams related only to work or he might say he never dreams about work.

If he suspects how you feel, asking the question might concern him and it could have an affect on how you two work together, so that is a risk.The bottom line is that you need to decide what you want to do about work and your feelings for your boss. If you think the best way to keep your job is to keep your feelings secret, you had better not mention your dreams.I don’t think you would be terrified of your dreams if you thought a romantic relationship was possible.

So, you need to find ways to move past your personal feelings and focus only on work. One way to do that is to act the role you know is correct and keep acting until you have your feelings under control.One young woman told me she pretended her boss was a favorite brother. She said after doing that for several months she got over thinking of him as a possibly romance (which was a good thing because he was happily married and still is).I think it would also be a good idea for the two of you to not spend so much time alone together–that’s just being reasonable and practical. You may be able to have some control over that. It isn’t good to spend so much time at work anyway. Work to discover a life away from work and find fun and friendships in those new places when possible. Best wishes to you with this challenging situation.

Tina Lewis Rowe

Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.