Dear Wendy
Dear Wendy

Afternoon Quickie: “Is It Too Late to Have a Relationship with My Co-Worker?”

Office romance
I work with a man who has been my friend for several years. We have both been in and out of other relationships over the years. Over the past year or so we have gotten a lot closer. We spend time together alone frequently. He compliments me physically, and we were intimate once. We never had “the talk” and just let everything run its course. I have developed romantic feelings for him and was too afraid to say anything because I didn’t want to affect our friendship and working relationship. After we slept together, things seemed to be going down the romance path but then all of a sudden just stopped. I was hurt, confused, and disappointed. I decided to say something to him, and at first he said he felt the exact same way. He had developed feelings for me but was too scared to say anything and thought I was only interested in a casual, one-time fling. He then said he has met someone else and is pursuing things with her. It is still very early with them, so my question is: Do you think it is too late for us? We have a long history together, and, while we also have clearly had communication issues, everything is all out on the table now. Am I foolish for hoping he will think about our conversation and give us a chance? — Hopelessly Optimistic

Sorry, but I do think it’s too late for you. Or, more accurately, I think it’s still not the right time. You work together, so there’s potential for a lot of discomfort (and worse) if you pursue him and things don’t work out. And because there’s already some history between you and nothing really progressed, that suggests that either feelings weren’t strong enough in the first place or one or both of you had hesitations about moving things forward. The bottom line is you’ve expressed yourself already and, if this guy were truly interested in having a relationship with you now, he wouldn’t continue pursuing a relationship with someone else. Sure, he may think about what you’ve said and change his mind and break things off with the new woman, but pinning your hopes on that and waiting in expectation isn’t going to do you any good, especially considering you work with the guy. Your best bet is to accept that he’s moved on and that you should, too. If things change at some point and you’re both open to a potential relationship together, you can be pleasantly surprised, but for now consider what you have to be a professional and platonic friendship only, regardless of your long history.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

5 comments… add one
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    kare October 2, 2014, 1:15 pm

    My boyfriend is my coworker (same office, different team). We were both in and out of other relationships and always friends. Once we were both single at the same time, we hung out and thinks quickly escalated. After we initially hooked up, the romantic path just naturally fell into place. At one point we did verbally discuss the actual title, but it was implied long before that. Based on my experiences, I would say the timing isn’t right for this guy. You guys hooked up and he started pursuing someone else. If he wanted to be with you, he’d be focused on pursuing you.

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    Raccoon eyes October 2, 2014, 2:10 pm

    LW, I too used to want to pin hopes and stuff on guys who just werent available for whatever reason. You need to chalk this up as in the past and leave it there. It is so easy to (endlessly) play the “what if?” game. But it usually doesnt end well for the person playing it, if ever. Also, you dont want to be the girl mooning over the guy at work who is obviously not returning your feelings.
    When you meet your special someone, they feel it too. They want it too. It isnt some epic battle to be together- you just are together because you both want it to be and it is the right time for you both, and you make each other happier than you ever were before. Look for that. Not with this guy.

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  • Muffy October 2, 2014, 2:13 pm

    I think this won’t work because he told you after he found out you were interested in him that he still wanted to pursue another woman. Don’t wait around because you will just be the filler girl until he finds someone new if things don’t work out with him and this other woman

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    Kate B. October 2, 2014, 2:37 pm

    If he’s actively pursuing someone else, your only decent choice is to butt out. If, and only if, his relationship with this girl ends, then you can bring it up again. But if he shoots you down a second time, move on.

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  • Essie October 2, 2014, 4:10 pm

    It is too late, and it’s time to move on. He was letting you down nicely by telling you that he’s seeing someone else, that means ‘…..so I won’t be getting into a relationship with you.’ The cards were all on the table, he knows how you feel, and his answer was to start seeing someone else. I’m sorry.

    It doesn’t matter if it’s early in their relationship or not, it’s really, really uncool to pursue someone who’s in a relationship. Don’t go there. It will only become embarrassing in the end, and especially since you work together. You don’t want be the star of office gossip about “that girl who won’t leave poor Bob alone.”

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