Find answers to some of the more frequently asked questions on the Forums.

Forums guidelines

Our guidelines keep the Forums a safe place for people to share and learn information.

Co-worker crush

Community Member

I'm looking for some advice as I have absolutely no experience with relationships. I'm in my mid 20s and I've never dated anyone and am super self conscious about this.

There is a guy that I work with that I have had a crush on for like four years. He's the only guy I can honestly say that I've ever been legitimately interested in, but I really don't know what to do about it. I feel like I'm terrible at reading the signs and can't tell if he is interested in me. I feel like maybe in the past he may have been trying to flirt with me, but I was too naïve to notice and that I have blown my chance. I'm too scared to actually go for it and ask him out, particularly since we are good friends and we still work together. I don't want to ruin that, or have things become awkward at work.

But I also am really struggling to stop thinking about him. I tried to make peace with the fact that we would probably never be more than friends, particularly with him being a few years older than me. But I still have really strong feelings for him, and it can be hard at work. Whenever I talk to or message him I always feel like I'm being annoying, as I've never been any good at keeping friendships either. I just don't know what to do, I don't know how to navigate these feelings as I've never dated or broken up with anyone or had to move on. Any advice would be appreciated!

5 Replies 5

Champion Alumni
Champion Alumni

Hello Sleepfox, thanks for your comment and it's not easy to date someone that you're interested in and who you work with, but it happens so many times, but the upsetting part is if you see them with another person, maybe at Xmas drinks or whatever, that's when you had only wished you had asked them out.

If you do happen to ask him and I'm sure that he would have noticed you looking at him, there will be times when you show pure devotion and times when you might have had a tiff, both may affect your work or perhaps it has already, but perhaps the latter of these may distract you more, but all relationships are exactly the same, whether you're working with each other or not.

At some point in life, 'you have to grab the bull by its horns', so do you know when he has a coffee break or lunchtime, then if it's the same time as what you have, then accidentally (on purpose) bump into him, don't forget he might be thinking the same way as what you're thinking and worry that you already have a partner, even though you haven't, doesn't mean that he knows this, then ask him something general, like did you watch the AFL grand final and who were you barracking for, there's nothing wrong with saying that, it's just a question many people would have been doing last weekend.

Watch how he reacts and if it's with a smile, grin and show of interest then ask him who he barracks for, then the conversation will develop, then each morning before work begins, be there to say hello to him with a smile, then he might be brave enough to ask you out.

Try and touch his hands by accident, this always draws 2 people together, ask him if he'd like to have a drink after work, don't worry about your nerves, this always happens even after you've dated many a person.

I'd love to hear what you think.


Community Champion
Community Champion

Dear Sleepyfox~

Welcome back, I'm sorry that things have not worked out better for you and you you have the same problem. It is a difficult and worrying situation for you, however it does not look like your feelings are going to end anytime soon.

I guess I'd better say right at that start that workplace relationships (even assuming neither party had a marriage or other attachment) can become awkward if they do not succeed long-term, and this is something you might find harder than your current situation. How do you think you would handle that situation -better then the current one or worse?

If you really dislike being in this limbo situation you may be prepared to take the risk, if that is the case and it was me I personally would not take a very direct approach, leaving room for either party to back out gracefully. As an example after a wearing day suggest a cup of coffee and see where that leads.

For any relationship to start it really does take two people, both of whom are prepared to assist in getting it going -it is not all up to you (even if it seems like it at the moment)

Do you happen to have a freind at work you can talk this over with to see things from an outsider's perspective? Sometimes others can see what we do not.

I also think that Mark's (Matchy69) suggestion that the more people you talk with and the more ease you gain in social situations the easier the whole matter will become. Have you considered it might be worth joining some sort of group -work related or otherwise -with this in mind?

I'm not sure your current age, or lack of experience in teen dating will make that much difference when you do find a serious relationship. It's not really a race.

Please fell most welcome to keep on discussing this, I'm sure there are many here who will have felt similar


Valued Contributor
Valued Contributor

Hi there SleepyFox and thanks for reaching out!

Croix and Groff have given some good advice - I'd like to offer some thoughts from a slightly different perspective, and will try not to waffle.

I have actually had a colleague who reported to me who was in exactly the same situation as you - long story short, they are happily married with a beautiful baby!

Here's my suggestions:

1. Think long and hard about what impact it might have on your career or his if the two of you became a unit. There is nothing at all wrong with a couple working together in a company as long as it's in the open and the boundaries have been set. It will be much more tricky if one of you reported to the other, as this can easily set up jealousy amongst others and calls of favouritism. If not, that's fine!

2. By all means chat it over with a colleague you can fully trust. Be careful here as you don't want that person dobbing you in, so to speak. This leads to an opportunity for you to ask your friend to mention to the guy that you are interested in him, and get his reaction. All she has to ask is how he'd feel about going out with you as you think he is a decent person. He can only say no! Then go and see him and ask if he didn't mind your friend approaching him as you were too shy. This is another chance for him to let you know if he is interested!

3. Write him a letter, handwritten, seal it in an envelope, and leave it on his desk with his name on it. Tell him you are very shy and not brave enough to ask him directly, but how would he feel about having a coffee with you one day? Be sure to ask if he wouldn't mind keeping your letter to himself please. Again, the worst that can happen is for him to say no. At least that has broken the ice and your relationship should be much more open after that!

The letter approach was the one that my colleague used - successfully!

If the two of you do start dating outside work, ensure you don't keep it hidden as this creates gossip. Be open and even tell your colleagues that you are dating.

There you go - I think I did rave a bit but really want you to get to know this guy better as you sound like a great person!

All the very best, very happy to discuss further if that would help you.

Be brave and good luck!

The Bro

Champion Alumni
Champion Alumni

Hey sleepyfox,

Thank you for reaching out and having the courage to ask for help. I think you are in a tough situation because the person you like is a coworker, but i could provide you with some help as i have been in a similar situation. I had a crush also on a coworker, I didn't think deeply about the consequences of my actions and I ended up also misreading the signals. If you are close friends, then it can be easier to hint at your feelings, but before you do, I would suggest to double check he isn't seeing anyone already, which happened is what happened to me. If there is no one in his life, then you might have a chance. But really think about how this will affect your relationship if it doesn't work out, as it might be awkward to be around each other at work and you might loose the friendship. If you are content with what might happen if he doesn't have feelings for you, then go for it. For me things didn't go my way and we stopped being close friends, however, later on, we ended up talking and we are great friends now. Sometimes feelings can cloud ones judgement and that's what happened to me. My advice would be think about it in terms of your friendship with him and your job, if you are ok with these consequences, then make the decision that you think is best for you. Ultimately, if you do go for it, it either works out, which is a great outcome or it doesn't. If it doesn't then it isn't meant to be and you can finally move on and look for something better. Hope this helps.

Community Champion
Community Champion

Hi sleepyfox,

I know it can be intimidating having a crush with no dating experience. I was once you, although I was a shy teenager! I had my first proper boyfriend right when I turned 18, and we are still together (I am 20 now) and I only was able to know he liked me because I knew what signs I had missed in the past. Plus, he was really into me and stopped at nothing to try and see me. I know some guys are shy too, so keep that in mind. But if they want to make things happen, they will.

Now, this doesn't mean you shouldn't try. You could try talking or flirting with him more and maybe bring up the fact that you have feelings for him. If you don't know if you never try, right? It is hard full stop to start new relationships, especially if you have never had one before. My advice would be to trust the process and try and put yourself out there more.

When the time is right, it will happen.