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Love Letters

Can I be friends with my work crush? How about if he has a girlfriend?

He’s living with someone, but I don’t think they’re happy. And I like him so much!

I have an obsessive crush on my project manager. He’s living with his girlfriend whom he rarely talks about. I get the impression things aren’t going well. We work together outdoors for long hours. We’ll be slogging away in the crummiest conditions and still have such fun it feels like a vacation. He makes me laugh until I keel over crying in a heap. I can’t tell if there’s tension or if it’s all in my head, but when we’re working alone we constantly make inappropriate sexual jokes, and I found out he changed his contact for me in his phone to a nickname he gave me.


I try to hide my feelings but I think our chemistry is hard to ignore. My friends tell me to tread carefully, so I am trying to focus on other things and dating other people, but this has been going on for months and I cannot get my mind off him. I am thinking of asking him to hang out outside of work. I won’t make any romantic advances as long as he’s in a relationship, but is it wrong to pursue a friendship outside of work given how I feel? Or do I have to wait in the wings until hopefully one day he breaks things off with his girlfriend? Please help; my friends are sick of hearing about this.

— Hopefully not another Jolene

A. Jolene, Jolene, JoLENE, JOLENE!

You say you get the impression things aren’t going well with his girlfriend, but he rarely talks about her. Make no assumptions, please.

I won’t make any romantic advances as long as he’s in a relationship.

At this point, asking for social time outside of work is an advance (sorry). With anyone else, it would be about friendship, but with this guy, there’s an “obsessive crush.” You want to spend more time with him because you like like him. Please don’t pretend it can be about anything else right now.


He has not asked you for quality time outside of work, which means he’s maintaining a boundary. Respect that and try to broaden your fantasy life. I know how obsessive crushes work; it’s difficult to imagine a relationship (or sex) with anyone else. But think about it this way: If he showed up tomorrow single and you started dating, the stakes would feel so high because you’re so into him.

If you can take the obsession out of the crush and see him as an actual, flawed, multidimensional human (one who is flirting like crazy, apparently, with someone who clearly is into him, all while he’s still living with a girlfriend), you’ll have a better shot at something real with him, whatever that might be.

Look at others. Talk to others. Date others. Do this for you because longing for him will take over your life. It will also make your real friends very tired.

— Meredith


If this guy wanted to be with you, he’d dump his girlfriend and be with you. You’re an amusing work distraction and nothing more. ZEPTEMBER

Do not ask this person to hang outside of work. You have feelings for him and you know he’s in a relationship. THENURSE

That this man is living with his GF should give you even more reason to stop all of this. Grow up and pursue your love interests outside of the workplace. The end. LUPELOVE


Catch Season 5 of Meredith Goldstein’s Love Letters podcast at loveletters.show or wherever you listen.