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Do I confess my feelings to my boss before moving to the other side of the world?

405 replies

scaredaboutwork · 03/09/2026 14:33

I’ve fallen in love with my boss. We are both 28. He’s not technically my line manager, but he’s one of two team leaders, so there is obviously still a work dynamic there.

I’ve genuinely never felt like this about anyone before. We’ve grown really close over the last few months and hang out outside of work sometimes, just the two of us. Nothing has actually happened and it’s all been platonic, but I feel like there is something between us.

I think he likes me too, but obviously I can’t know for sure.

There have been enough moments/signs that make me think I’m not imagining it, but I also know when you really like someone you can read into things.

My feeling is that if it is mutual, we’ve both probably avoided actually doing anything about it because 1) we work together, 2) he’s in a more senior position, and 3) neither of us wants to risk rejection and then have to see each other at work afterwards.

Which brings me to the problem.

I’ve been offered a job in Australia, starting in the New Year.

If he wasn’t in the picture, this would already be a huge life decision, but now I feel completely torn.

Part of me thinks I should just take the opportunity, go to Australia and accept that the timing with him was wrong. I also know that realistically pursuing something while I’m still working with him could get complicated.

But I keep imagining myself sitting on the flight wondering whether I’ve just walked away from someone I could have had something really special with because neither of us was brave enough to say anything. As I said earlier, I’ve literally never felt this way before.

At the same time, the idea of confessing how I feel terrifies me. If I’ve completely misread him, I’ve potentially made our friendship and working relationship awkward right before I leave.

Would you tell him before deciding?

OP posts:
whackwhackoops · Today 08:15

Datgal · 03/09/2026 15:09

Fuck it. I'd tell him. You'd always be wondering what if....He can always get a two (might even be 3 now) working visa and come with. Life's too short.

This… he asked you on a date before and you socialise outside of work I can’t see the dilemma at all

Supperlite · Today 08:28

I initiated the conversation about feelings with my last boyfriend. He is now my husband. I have previously initiated a conversation where my friend did not reciprocate, but was flattered. It is not embarrassing to admit your feelings for someone if they don’t reciprocate - it’s always nice to hear someone likes you. There is nothing wrong with the genuinely amazing men I am friends with, they just aren’t my cup of tea. My husband is. In the same way, if you tell him you have feelings for him and he doesn’t reciprocate, that’s fine, there’s nothing wrong with you, you’re just not his cup of tea. No big deal.

You could say something along the lines of, I really enjoy your friendship and if I am honest I would love to be more than friends with you, and I wondered if you felt the same?

Surgz · Today 08:32

If hes single i would tell him. You have nothing to lose. Tell him of the offer, say its an exciting opp , mention how much you will miss him, tell /ask him I may have got this wrong but ... ??? If he reciprocates stay in touch, if he doesnt go freely knowing you said it!
However, Dont have a 'goodbye shag' that is him taking the opportunity and will mess up your life in Oz

GreenHuia · Today 08:53

scaredaboutwork · 03/09/2026 15:18

He’s actually a Kiwi who used to live in Australia!

He aha te mea nui o te ao
What is the most important thing in the world?
He tangata, he tangata, he tangata
It is the people, it is the people, it is the people
A Māori proverb since he's a Kiwi bloke. Tell him! I think you would always regret it if you don't.

user1492757084 · Today 09:08

Tell him you will miss him as you really enjoy his company and that he is welcome to visit.
Leave the ball in his court.

If Australia is fleeting and you return you can always ask his assistance in finding a job. This will be possible if he has not rejected your deep declarations of love.

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