He Has a Crush On His Boss - Relationship Advice

I really need your no nonsense advice. I'm an admin and I work for an incredible woman. I have developed quite a crush on her. When I first took the job about a year ago we had one night together. We said it didn't mean anything. Well here I am a year later and I'm still stuck on her. This is so complicated. There's of course the boss part of this, and not shitting where you eat. But then there's also the age difference. She's got a good 20 years on me. When we're at work there is a tension between us. There always has been. I think that's why she hired me. She seems to thrive at her job when she's a little worked up. She makes comments and will brush up against me. I know the entire situation is just completely unprofessional. She goes off on dates and smiles as if it's not a problem. if I say I have a date she smiles and doesn't care, but I'm lying. I don't want to date anyone. I just want her.

We work in the entertainment industry so it's not uncommon for people to have these kinds of relationships. As far as bosses go she's great. She talks me up to others and makes sure i get credit for my ideas. I love my job and I don't want to blow this but I am obsessed with this woman. What should I do? Should I quit? Should I tell her how I feel honestly?

Justin

I'm going to assume you are in your early twenties, legally an adult, and that your boss is in her forties.

I'm also going to assume you're in LA or somewhere thereabouts.

You are right, this is complicated. You hit two of the points - one is the age difference, and one being that she's you're boss and like you said, you really should not shit where you eat. And then there's another aspect to this: it's the power exchange. There's a part of you that can embrace the submissive role. I'm not saying you are heading toward a full-on power exchange lifestyle. But I am adding that this is another dynamic to your crush. It's nice to be able to surrender control and be taken over when you feel completely safe with a trusting and committed partner. I understand the erotic part of what you're going through in that aspect.

The good news is none of these things is life threatening, if you were to get together. You're consenting adults in an industry and a place that hosts the Demi-Ashton union. Like you said, people in the entertainment industry aren't strangers to dating coworkers, and they aren't adverse to Cougar or May-December relationships.

The bad news is, this situation has a very big possibility of total failure. And then what. Would you lose your job? Would she be vindictive? Could this affect your ability to find future work?

I'm going to say something here that you aren't going to want to hear, but take it from an older woman's experience. You are a very young man. Your frontal lobes have most likely just developed. You are growing and changing in many ways every day. Just think back to the kinds of girls you were attracted to when you were 18, or the first girl you really loved and swore it would be forever. That's all changed now, hasn't it. And you will continue to change. You will go through more changes before you turn 30 than you can even fathom.

This obsession with this woman is going to fade. In the not so distant future, it won't be as maddening as it is right now.

Part of why you are obsessed is because you can't have her. This does not make you a dick. This just makes you a normal healthy young man. Guys are kind of hardwired for game playing. They love the chase, they thrive on the thrill of competition. They tend not to go for things that are too easy. Not with their hearts and their minds anyway. They prefer to rise up to a challenge.

I almost want to suggest that this woman played a perfect hand here. After hiring you she allowed the two of you to be swept up in a moment. And then she said it was nothing and forget about it, and go back to working for her as if it didn't happen. Perfect catch and release. She may have anticipated how you'd react to that. You said she enjoys the tension in the office and she is a little dominant. She set you up in a very perfect submissive and interested role, puppy dogging around after her, becoming the perfect assistant and feeling mildly obsessed with her. Smart woman, that one.

Women can be quite conniving and tricky like this. Many women know exactly how to keep a guy right there at arm's length wanting more. I don't think this was this big set up or anything evil. I'm just saying that it is possible she let the situation you're in occur.

And what do you get out of this arrangement? Well, you got the fun and memory of that one night. You have a job you enjoy. And like you said she's a good boss, giving you credit and praise and helping to build your career. Your bosslady probably sees the whole thing as harmless and fun. I doubt she's dismissing you when she smiles that you have a date, and I doubt she's trying to torture you when she goes out with a man.

She may not realize the extent of your crush. There is a whole pattern of how women behave when they are playing you. I'm not seeing that pattern here. I do see the possibility that she allowed this to happen, but I don't see any mal-intent or cruelness.

My advice is to enjoy the tension you helped create, but get on with your life. You don't have to quit, and you don't have to do anything about this. Just start trying to see it for what it is, and move on from it by dating women outside of your office. If you have found you enjoy dating older women and don't feel she was the exception, than you are free to do that. After dating high school and college girls it might be very cool for you to date older, mature, successful and established women with whom you're not so much in charge. It's a completely different dynamic, and you are free to explore it.

Just as she enjoys the tension and playful feeling of the two of you in the office, you might be enjoying it too. This may be one of the reasons your work is so good. You are allowed to enjoy it for what it is and not excelerate it to the next level. I meant it when I said your wants will change as you grow. You may find that once you stop clenching down on this that you free yourself up from it quicker than you're thinking.

Chalk this up to experience and try to get some perspective on it. It sounds like it's made quite an impression on you. As long as you can keep your wits about you and your feet on the ground, this will be something you refer back to years from now with a grin.

Unfortunately it's not always easy to get the emotions in line. If you give it a shot and you just can't, then my next suggestion is to talk to her. In a humble and non-confrontational way, privately just tell her that you are having a hard time letting go of that one night the way you had both agreed. Tell her you're working on it and you don't want to do anything that will jeopardize your working relationship but that you felt you should tell her that you're struggling a little to get those feelings you have in check.

That way, she knows those previously harmless bumps and teases are really not OK anymore. It sort of puts the ball in her court. She may be surprised at how deeply you crushed, expecting a much less committed flirty feel from you. Just confessing it to her will help relieve its pressure in you.

Is there a chance this is reciprocal and she'll want to explore furthering your non-professional relationship? Of course there is, but honey I really don't want you to bank on that. I don't think that's the case. I think this is what it is, and you just need to get a grip and all will be well.

I know it sounds like I'm dismissing your feelings. I'm really not. I know how headstrong and focused a guy can be when he gets all turned-around like this for the first time. Does it help at all if I say this is normal, and healthy, and you aren't the only person that's ever gone through something like this? Believe me, a year from now you will look back on this with a lighter perspective.

Namaste.

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