Make It Stop: “Help, I Love My Boss, How Do I Fix That, Or Should I?”

I have feelings for “Luke”, my superior at work. He’s married but currently separated. I know it sounds cliche, but hear me out. We work closely; he’s like my Obi Wan Kenobi. He makes me laugh and he means a lot to me. However, we crossed some boundaries when we socialize outside of work. He’s confided personal issues to me and I’ve divulged personal details to him too. I don’t know if he’s attracted to me or what, but that isn’t the issue. I’ve already decided I shouldn’t act on it. The problem is I don’t know how to stop my feelings for him! I’ve tried distancing myself, but he doesn’t understand why, and the space between us seems to hurt him. The distance also makes me upset, so I’ve just given up. I want our work relationship to stay the same, but I know I also want more than that. It’s driving me mad. Without our closeness, I would feel lost at work, but with it, my attraction is growing stronger. What should I do?

Luke sounds like a manipulative d-bag. It sounds like he’s using you to feel young, charming, and funny. Stop playing into this dynamic. He’s not your Obi Wan Kenobi, he’s the sad guy at the dive bar weeping into his Blue Moon hoping you’ll pity-fuck him at last call.

Wait, I’m getting ahead of myself. Let me reel it in. Whew. Deep breaths.

I’m glad you decided not to pursue anything with him. Because from what you’ve told me, red flags are all over the place. His willingness to cross professional boundaries makes him look immature at best, and exploitative at worst. As your superior, it wasn’t right for him to blur those boundaries.

It probably feels incredible to have his attention, to be the audience to his smooth charm and crackling wit. But from where I sit, given his troubled personal life, his motivations concern me. It sounds like he’s using you for a cheap self-esteem boost. Maybe his marriage separation bruised his ego. Maybe he wants to know if he can still make a pretty woman convulse with laughter at his Star Wars jokes. None of that excuses his outrageous behavior.

Is it possible he’s a nice guy who’s going through a tough time and is looking for a light in the storm? Sure. But given he’s in a position of authority over you and his pouting when you assert your boundaries, it’s—everybody say it with me!—inappropriate.

Maybe I’m jaded, but I wouldn’t think too much about the personal issues he’s told you. It’s possible they’re exaggerated, untrue or he said it to elicit your sympathy and secure your attention a little longer. It sounds like you’re easy to talk to and fun to impress. The twinkle in your eye reflects the person he wants to be. Why wouldn’t he want this fawn-fest to continue, right? But it has to end. Luke needs to be out of the “crush” column and into the “friendly acquaintance at work” column ASAP.

How do you get over someone? You make a decision to move on and change your behavior. Stop treating him like a crush. Treat him like a superior. Don’t discuss your personal life or his ever again. Give small smiles, not lingering belly laughs. Does it suck? Yes. Will it feel weird? Of course. But, unfortunately, you’re the one who has to be the adult in this situation. And you’re in charge of protecting your heart, not him.

As for his confusion when you pull away, he’ll have to get over it. The fact that he feels “hurt” over having some healthy space between you two shows he needs a reality check pronto. If he takes you aside and asks what’s wrong, resist the urge to confess how you need to disconnect from him. Be upbeat, firm, and cordial. Everything’s fine. I’ll have those files you asked for later this afternoon.
Of course, as you reel in this flirty behavior, it might put a strain on your working relationship. You might even need to look for another job if he retaliates in response to your decision to shift the dynamics. If a guy is immature enough to blur your working boundaries as flagrantly as he has, I wouldn’t put it past him to lash out when you disengage. It’s a tough lesson to learn but one you’ll never forget: when a problem arises with a superior, you’re the one who’s position in the workplace is usually vulnerable.

Take some time and mourn what you had with Luke. When you’re ready, own up to the part you played in this mess. You both used each other. He basked in your starry-eyed attention, you felt the warm glow of his emotional vulnerability. Forgive yourself for not knowing any better.

There’s been a void you’re filling with this dead-end crush, so fill that void. Find someone else. Date. A lot. Bump it to the top of your priority list. Make an effort to connect with someone who has more to offer you. Something real. Something on equal footing.

Lastly, be thankful for this crush. It alerted you to the fact that you’re ready to have someone more emotionally available in your life. That’s a good thing! Follow that impulse, wherever it takes you, and meet it with an open heart.