My Crush And My Boss

This one’s long, juicy, and complicated. Just remember as you read my answer: I don’t work in human resources.


Oh Meredith,
This one is both an ethical and a love question and I am in dire need of advice. Literally, three careers could hang in the balance.
I’m an intern at a fairly large corporation here in Boston. (For obvious reasons, the company will remain nameless, but trust me, you’ve heard of it.) I’ve been working there for several months and I love every aspect of my job. If I had my way, it’s where I’d work full-time once I graduate in about a year.
One of the great things about my already fantastic job is my fellow intern, who I will call Jim. He goes to the same university as me (though we hadn’t met before this job) and we really get along well. I’ve come to consider him a close friend, and, if I’m being honest with myself, I’ve always hoped that it would become something more after we finish our internships. The flirting has been undeniable, and it seems apparent to others in the office judging from some lighthearted comments from coworkers about how we’d be perfect for each other.
Everything between us had been innocent until the entire department went out for drinks a couple months ago. We all got a little more intoxicated than we should have and Jim and I were put in a cab to go to our separate homes. The details are hazy, but I do specifically remember some very clumsy making out happening in the back of that cab. Though we never talked about it, we continued to grow closer and closer.
Now fast forward to last week, when things got complicated. Jim confided in me that he and a coworker of ours, who I’m calling Karen, have been making grilled cheeses and having late night pajama parties together for about a month now. Karen is a decade older than us. She’s also our boss. To be fair, she didn’t hire us (someone above her did that), but we do answer to her and work with her all day. Obviously Karen is an idiot for starting something with an intern, I know that much, but my problem is with how I reacted to the whole thing.
I literally felt sick to my stomach when he told me. He made me swear I wouldn’t tell anyone because of the obvious consequences, but it’s really starting to affect my work life in terms of how comfortable I am in the office with the two of them. Karen is not aware that I know.
I ended up telling Jim that we could be friends but I never want to hear about his and Karen’s activities ever again. So that’s where I left the situation with him for now. Oh — and just so you know, we did sign documents at the beginning of our internship promising that office romances with full-time employees would not happen.
My question is: What’s the appropriate reaction in this situation? I’m trying my best to make sure that it’s my logic that’s running the show and not my jealousy. It’s hard to do this without an outsider’s perspective. Can I be friends with Jim? Should I mention something to my friend and boss Michael Scott? How do I deal with Karen?
I wish I could forget I know, but now it’s become a larger-than-life elephant in the room.
Thanks for any insight. Hopefully you can help me sort this out before I explode!

– Pam, Boston


Your original question seemed to be about how to cope in the office, but your update implies that you’re more concerned with your feelings for Jim. That makes life easier for me. As I said before, I don’t work in human resources.
No one in this scenario is sloppy seconds, Pam. Jim liked you first. He made out with you long before he allowed himself to be seduced by Karen. I want to dislike him for not acknowledging the cab make-out after it happened, but you didn’t either. You’ve both been passive-aggressive about this crush. You’re both to blame for the relationship not moving forward.
I also want to dislike Jim for giving into Karen, but as he said, it’s a thrill. A stupid thrill, but a thrill nonetheless. Jim is young. He’s still learning that his romantic actions have consequences. That’s not shocking, assuming that he’s still in college. And that’s why this sounds like classic sexual harassment to me.
I blame Karen for this, which is why I wouldn’t feel too icky about Jim. I mean, go ahead and feel icky that Jim and Karen have been together, but don’t assume that Jim is now somehow tainted forever. He’s in the middle of a big life lesson and it sounds like he’s already figuring that out.
You’re also in the middle of a life lesson. Jim has to learn to think before he acts, and you need to learn to put your feelings on the line. Tell Jim that you were hoping for more after the cab make-out session but that you didn’t have the courage to tell him at the time. Then explain that the Karen situation made you feel icky about him, but that you still hope there’s potential for him to have a non-icky relationship with you.
My guess is that he’ll drop Karen and jump at the chance to be with you. That seems to be what he wants to do. If it turns out that you’re not what he wants, well, you put yourself out there, and you’ll never have to wonder.
My fear, of course, is that after he does decide to be with you, Karen won’t be a happy boss. Please know that if she does make life difficult for you (or Jim), you can always run to HR (Toby) or Karen’s boss (Michael Scott). That’s your right no matter what promises you’ve made.
Readers? Is Jim immature and a victim of sexual harassment or is he just a cad? Should Pam tell Jim how she really feels? Should she even consider Jim after what’s happened with Karen? Discuss.

– Meredith

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