3 minute read

Advice given on May 23, 2022.

Coworker Confusion

Hey Jay,

I’ve got a workplace situation I’m hoping you can help me with. I’ve been at my latest job for about a month, and I’m having trouble befriending one of my coworkers. We don’t work directly together, but we do sit in the same room, along with a number of other people. At first, I thought he just didn’t like me, but I’ve found I get along with everyone else in our office. I’ve been trying to be as friendly as I can be by offering to grab lunch, trying to chat when we happen to be at the water cooler together, and inviting him to join me and our other co-workers when we get together after work. He is never outright rude to me, but his answers are usually pretty curt, and our conversations, as a result, are very short. Do you have any advice for me? I am not sure if this guy doesn’t like me, or if he’s just not very sociable. What should I do? How can I get this co-worker of mine to open up and be my friend?

Confounded Colleague


You sound like you have such good intentions, I’m sorry you haven’t been able to befriend this coworker of yours. It sounds like you’ve done some self-reflection to see if you are the problem. Since you’re friends with many of your other coworkers, I agree that you are probably not someone incapable of making friends. It could be that this coworker of yours just doesn’t want to make any friends in the office. Maybe they are thinking about work when you try to chat with them at the water cooler, and so their mind isn’t on your conversation and they give you short replies. I think there are a million possible reasons this person isn’t warming up to you. The real question I have for you, is why does this bother you so much? It sounds like you’ve got a group of your colleagues that you hang out with and are friends with. I’d suggest you leave this guy alone, and let him do his own thing, and you can talk to and hang out with your friends. You’ve made it clear you are willing to be friendly with him, so he should have gotten the hint that you’re happy to talk to or spend time with him if he so chooses. I think you have done all you can do, and now it is up to your coworker to decide to engage in this friendship if he wants one. Don’t stress about it, not everyone gets along as fast friends.



Colleague Crush

Hey Jay,

So we had a new person join my company a few months ago, and he’s such a great guy. I didn’t mean to, but I totally have a crush on him, and I’ve tried to drop him hints by timing my coffee breaks to line up with his, and joining him for lunch outside. The problem is, he doesn’t seem to have a clue! I don’t want to do anything inappropriate or create an awkward situation at work, so what should I do now? Can I confess my true feelings for this guy?



Sounds like you’re in a bit of a pickle for sure. I think you know what I’m going to tell you, but it just isn’t what you want to hear. The best thing you can do for your career, and to maintain your workplace environment, is to drop it and stop pursuing this guy, no matter how careful you have been so far. For all you know, you may be putting this guy in a very awkward position. He might not be as clueless as you think, but doesn’t know how to politely reject your advances and is instead trying to ignore them. If you can’t drop this, I think you can certainly tell him how you feel. But if you go down that route I think you should just be direct, and find a way to have that conversation that isn’t awkward, regardless of what his answer is.

Good luck,