[DeltaGOC]

I’m struggling with feelings I have toward a co-worker of 4 years. I’m a 40 year old male and she’s 26. We acknowledge that we’re good friends and close and have confided in one another in the past regarding an array of issues. She is currently involved in a 3 year relationship that has a business arrangement feel, not one of a match made in heaven and she has admitted that. On a recent business trip, we had adjoining rooms (her suggestion) and the door stayed open through the night after we laid on her bed for a couple hours talking about personal things. For example, she prefers to sleep naked. She even left the bathroom door open while showering the next day. During our most recent trip, her and another male co-worker unexpectedly stayed over in my room with only 2 double beds. I woke to find her in my bed, her back toward me, our legs intertwined and my hand on her back. Nothing else happened and we didn’t speak of it. The two of us have another conference coming up and we’re sharing a suite with beds in separate rooms. Quite unusual I’m aware. I keep telling myself that I’m reading too much into it because of the age gap and her current relationship, but am I? Is she into me? Is she waiting for me to push the issue? Is she playing head games? Don’t know what to do because I’m also her boss.

[April Masini, your AskApril]

First of all, you’re not reading into this. She wants you to make a move. Second of all, the age gap isn’t a big deal here…. you’re both adults. However, the biggest problem is the fact that you’re her boss, and there’s a power gap. When you date an employee, you may be liable for all sorts of legal issues like favoring her over others, or if there’s a break up, punishing her by not giving her raises, projects, perks — because of the personal relationship. That said, lots of bosses and employees have happy relationships and even marriages, but you should be aware of your company’s legal policies regarding dating in the workplace.

My advice is that you take this relationship out of the shadow lands, where she winds up in your bed, sleeps naked in an adjoining hotel room with the door open, etc. and ask her out on a date, if that’s what you want to do. This will bring the issue of her boyfriend to the forefront, and you’ll get a lot more clarity than you are now. When you do ask her out (if you do), make sure you use the word “date” in the asking — especially since this relationship is so murky, it’s important to bring some light to what it is. Define it as dating by saying it’s dating.

Hope that helps! Let me know how things go.

[Member]

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