I Like My Boss A Lot! What Should I Do?

Question: I really like my boss. He is super nice and funny and when he is around me, he makes me laugh like crazy! He makes me smile 24/7. I really care about him and his feelings.

He recently broke up with his girlfriend after they had a huge fight. I asked him if everything was okay and he seemed really down, so I tried to talk to him and he seemed a little bit better. I wanted him to be happy, so I asked him what he wanted most and he answered ”A K-Bar”. It’s a type of knife. So, one day I looked on Amazon and bought it for him. When I went to work and gave him the gift he was the happiest Man Alive! I had never seen so much joy and happiness on his face!!

But, I really don’t know what to do. I really like him. Sometimes he will play around and act like he will smack my butt. Does that indicate that maybe he feels something for me? Every time I go to work he always gives me a BIG smile when I walk in the room. I need some advice because I don’t know what to do.

Response: You don’t say if your boss owns the business or if both of you are employed by an organization that has managers above your boss. If you are both employed by a company, be aware of the restrictions on relationships between bosses and employees. There are so many problems caused by such relationships, that most companies forbid anything that could even seem to be personal rather than professional. Your boss could be fired over what has already happened (taking a gift from an employee). You could be fired too, for giving him the gift. He could also be fired for encouraging your affectionate feelings for him.

So, one of the first things you should do, to protect your job and his, is to take a realistic look at what would happen if he was seen touching you, swatting you, taking gifts from you or behaving in a way that seemed romantic and personal, rather than focused on getting work done. If he owns the company and it is only you and him there, maybe you can continue your current behavior. If not, think about what you are risking.

Also, think about the reasonableness of a man who makes probably twice or three times as much as you do, taking an expensive gift from you. You shouldn’t have bought it, but he could have refused to take it. If he wanted a KA-BAR (K-Bar) knife so much, he could have bought it himself. I’m sure it did make him happy to get it, but that isn’t the point. The point is that buying your boss a gift to help him get over his bad feelings after breaking up with a girlfriend, isn’t a reasonable way to build a good relationship—personal or business. And it isn’t a very mature way for a male boss to behave toward a younger female employee.

I want you to also think about this: You knew he had a big fight with his girlfriend. You knew he was upset and depressed. Why would you want to give someone in that condition a military-style survival knife? I get the impression you don’t know your boss in any way except at work. You don’t know his girlfriend either—or what led to the fight and the break-up (except what he might have told you.) You don’t know his medical condition, his psychological condition or anything else about his personal life. You should not have gotten involved with any aspect of his feelings. Remind yourself that you are an employee, you are not a counselor. I also get the impression you are still of a youthful age, so you don’t have years and years of experience to guide you or to help you guide him. You can hurt someone rather than help them, by getting involved in a situation you don’t know about.

However, I realize that if you feel a lot of affection for your boss, you probably wish you could know for sure how he feels about you and if there is any future for the two of you. One way to know for sure is to quit your job and see if he still wants to spend time with you, when he can do it without any risk of getting in trouble. Instead of a few minutes of having fun at work, you might be able to spend a lot more time together. If you quit and find another job, then call him and ask if he’d like to have lunch or coffee, you’ll find out right away how interested he is in a relationship. I expect you don’t want to risk your job to find out, but that is one way to do it.

Or, if your job is not the one you intend to have for the rest of your working life, you could mention to your boss that you’ll have to find another job one day. Let him think about the time when you won’t be there. If he wants to have a personal relationship with you, he may say something about it then. If he says he’ll miss you at work, you could remind him that the two of you could still get together for coffee or just to talk. You might be able to tell by his reactions to that comment, whether or not it’s something he’s interested in.

You could mention a movie you’ve seen or a concert you’ve attended and you could say that you thought he would have liked it too. Then, you could say, “If you weren’t my boss, we could go to something like that.” See what he says. Or, after the two of you have laughed about something, you could say, “I think we could have a lot of fun away from work. If you weren’t my boss, is that something you’d like to do?” (If he says no, it will be very embarrassing. But, if he says yes, at least you will know where he stands.)

The risk of asking him or hinting strongly to him, is that he might feel pressured about it and look for ways to remove you from your job. That wouldn’t be good!

Another risk is that he will think you are available for a sexual relationship, without having a real dating relationship. If he has been sexually active with his former girlfriend, he will be looking for sexual activity elsewhere and may think that is what you’re interested in too. That could be disastrous for you in many ways, so be very, very careful about suggestions he makes that might involve more than you intended.

So, that brings us back to your question: What should you do? The answer to that will depend upon your ultimate goal for the relationship. If you just want to be able to laugh and enjoy your boss’s company, you can keep doing what you’re doing right now. Be a good employee and help both of you be successful in the company. If your goal is to date him and maybe to eventually be married to him, you will probably need to leave your job so the two of you can be free to know each other away from work.

Another question could be: What should you NOT do? My comments already have pointed out that you should not get involved with your boss’s personal life. You certainly should not buy any more gifts for him. You should not do anything that could cause gossip and speculation among other employees. You should not settle for only a sexual relationship. You also should not assume your boss is interested in you romantically, just because he likes you personally. Maybe he feels romantic, maybe he doesn’t. The old adage that “time will tell” is true here. For right now, focus on work and on being a valuable employee and coworker and give it a bit more time.

If you have a trusted friend or relative who has had successful relationships in his or her life, perhaps you could talk to them about the situation. They would know you and be better able to provide personalized advice.

Best wishes to you! If you have the time and want to do so, let us know what you decide to do and what happens.

Tina Rowe
Ask the Workplace Doctors

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.