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

438 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:
Xems · 03/09/2026 15:35

I was in a similar situation around 10 years ago but I already had the move to a different country planned when I met the guy and we knew each other for around 5 months before I left.
I was very torn about the move in general and worried things weren't going to work out etc. And now that I look back I think I was looking for a reason to stay where I was and have an excuse to back out of the move without having to admit that I'd bottled it.

In the end, I moved and things turned out well and I'm happy with the life I have built here and feel like I'm better off than I would have been staying in the UK. I have stayed in touch a bit with the guy and I'm glad that I didn't stay for him.

BillieWiper · 03/09/2026 15:34

I think he would have asked you out or at least flirted with you by now if he was interested.

I don't really see these situations where two people really like each other romantically but they just never ever say or do anything about it. Unless he's not single.

To place the future of your life on the chance this bloke might be your life partner seems like too high odds a bet.

Happyjoe · 03/09/2026 15:34

scaredaboutwork · 03/09/2026 15:19

Currently it is six months fixed term. If I enjoy it/they like me they will sponsor a skilled visa for me.

Tell him then and go to Oz. 6 months is nothing! You can get talking while away...

BeEagerRubyBird · 03/09/2026 15:32

PeonieLover · 03/09/2026 14:52

If he really liked you he would have made his feelings known but he hasn't so there's your answer.

Would a man let a potential life and career changing opportunity like an overseas move pass by due to a potential love interest? Very unlikely, think like a man and put yourself and your career first.

Don't make a fool of your self by declaring your love to someone you might need to ask for a professional reference in the future.

Edited

I'm not sure if he would have when he's her boss.

Lornaadoone · 03/09/2026 15:29

Go to Australia, it’s an amazing opportunity. No man is worth losing out on such a great adventure.

cbbo · 03/09/2026 15:29

Why don’t you drop australia into conversation in one of your meet ups outside of work and guage his reaction.

Williteverrainagain · 03/09/2026 15:28

Ayarreet · 03/09/2026 15:11

Spot on! 😂

I was thinking the same

Datgal · 03/09/2026 15:27

scaredaboutwork · 03/09/2026 15:18

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

That's great. No barriers really! I was in a similar ish position. Although I was going travelling for two years. Got with this guy who i'd liked for ages not long before going.
I still went.
I sent him a message about a month later saying I quite liked him and IF he was still single when I got back (he'd been single for years so thought I had a good chance!), we could rekindle etc. Anyway, he'd started seeing somebody!
This was years ago. He married her, had kids. Still see him as have mutual friend. I have a SO now.
Glad it all worked out like it did. I've caught him liking reform posts on FB...so I dodged a bullet! 😂
Anyway, that's a long winded way of actually saying...even though I said tell him. I would still go to Australia. It's not forever is it? You might even meet someone out there? Things just have a tendency to work out.... whatever that may be!

ClairDeLaLune · 03/09/2026 15:27

Faint heart never won fair gentleman OP! Go for it and tell him! You’ll always regret it if you don’t. And if he doesn’t feel the same way, you’ve got an easy get-out: Australia. You have nothing to lose!

You could start with saying that you regretted not saying yes to his suggestion of a date and you’d like to go on one with him, then see how it goes. And report back, obvs!

Okthenguys · 03/09/2026 15:26

I would tell him. If he isn’t interested then you’ll feel gutted for a few days then move to Australia and probably never see or think about him again. If he is interested then it will somehow work out. DH moved to Brazil for 3 years just 4 months after we met. We did long distance and have been happily married 11 years with 2 kids. If it’s meant to work out it somehow will, if not it won’t.

Maisy7 · 03/09/2026 15:26

Invite him for a coffee on the pretence you want to discuss something with him about a job you've been offered and you are not sure what to do...

That way you can see if he likes you, you can trust him, and whether there could be a future together.

The fact is you are very young and unless you go for it you will never know...if you are not sure about the new job then do some more research, stop thinking about it, and see what happens naturally.

If the guy is not interested and you have the opportunity, grab it! Sliding Doors moments that only you can control....so be happy.

Wishing you the best outcome.

OtterlyAstounding · 03/09/2026 15:24

scaredaboutwork · 03/09/2026 15:18

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

Oh, well, definitely tell him then. He could be pining after you, and you'd never know!

As a Kiwi, I think us women are very forward in terms of making the first move or putting out strong signs that we're interested, and thanks to that our men are (according to other cultures) pretty terrible at making the first move unless you're practically throwing yourself at them by other cultures' standards.

Disclaimer: Obvious generalisations, but still.

Missingducks · 03/09/2026 15:22

As you are already friends can you say something like

"I would genuinely appreciate your thoughts on this opportunity I have to move to Australia. It would be good for my career I think. You have also moved countries - what aren't I considering? And is there anything else I should be thinking about? Are you going to beg me to stay? "

scaredaboutwork · 03/09/2026 15:21

OtterlyAstounding · 03/09/2026 15:12

If you're not convinced about moving to Australia, totally separately to your feelings for him, then I like this idea! Something inviting him out by referencing the date invitation he made, at least.

Although really, what's the worst that can happen if you just tell him you like him fairly bluntly? If your confession is received poorly then you can just abscond to Australia - it's not like you have to stick around to live down the embarrassment Grin

I did say we should hang out more - and we booked the theatre for next week! So, I honestly don’t know if it’s a date or just friends hanging out. We also went to a concert last week. Nothing has ever happened though

OP posts:
Skyflier · 03/09/2026 15:20

I’d apologise for turning down his date offer and then say can you reconsider. He obviously does like you if he asked you out first.

Itiswhysofew · 03/09/2026 15:20

You don't want a romantic relationship with your boss, do you? Might be worth checking what the company policy is re that. Obvs you could get another job.

You could tell him, but still go to Aus and see how you feel when you're away from him, living a different life. You could also meet the love of your life oit thereSmile

Bluenotgreen · 03/09/2026 15:20

I would ask him for a drink after work. Tell him everything. About the job offer, your feelings for him, all of it.

Good luck!

F63C · 03/09/2026 15:19

scaredaboutwork · 03/09/2026 14:44

How would you suggest? I’ve never confessed my feelings before… the thought terrifies me!

You don't 'confess your feelings'. You will look like a lemon. Just ask him out for a drink and see how that goes. He might be a right muppet once you get to know him. If you tell him you have a crush on him you will cringe forever.

Let him do some of the running at least or it's all one sided and no-one wants that.

scaredaboutwork · 03/09/2026 15:19

Happyjoe · 03/09/2026 15:17

Go to Australia. Even if he does like you, that's a lot of pressure to put on someone - you giving up such an exciting opportunity for them, as soon as you get together. You may not think putting pressure on but I bet he would feel it.

How long are you working overseas? Perhaps try and keep in touch, create a friendship and then see if anything happens if you are both free upon your return. I don't think it's worth giving up Australia on a 'what if'. It's a great opportunity to see a bit of the world and who knows, you may meet someone over there too.

Currently it is six months fixed term. If I enjoy it/they like me they will sponsor a skilled visa for me.

OP posts:
scaredaboutwork · 03/09/2026 15:18

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.

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

OP posts:
Happyjoe · 03/09/2026 15:17

Go to Australia. Even if he does like you, that's a lot of pressure to put on someone - you giving up such an exciting opportunity for them, as soon as you get together. You may not think putting pressure on but I bet he would feel it.

How long are you working overseas? Perhaps try and keep in touch, create a friendship and then see if anything happens if you are both free upon your return. I don't think it's worth giving up Australia on a 'what if'. It's a great opportunity to see a bit of the world and who knows, you may meet someone over there too.

Fortheloveofplants · 03/09/2026 15:16

Assuming your current job is similar to the new opertunity (so he would know about the industry/type of work), and if your fairly close with him anyway (socialise outside of work the same way you do other friends) then tell him about the job. Talk through the pros and cons with him, approach it as if your asking for advice/his opinion.

His reaction/response may tell you more about his feelings towards you, it might prompt him to confess his feelings too if he doesn't want you to go, or he may remain completely platonic in his reaction, or even fully encourage you to go.

It may also help you decide about the job to discuss it with someone else familiar with it. Just make sure you make your final decision based on what's best for yourself

Here2talk · 03/09/2026 15:16

Personally I think go for it.

if he doesn’t feel the same, then I think that’s your answer to go to Oz and see how it goes.

can you keep us updated though? Because I’m invested.

MintedOnVinted · 03/09/2026 15:16

Do you feel like January was just two seconds ago? Because I do. A year is no time at all. Tell him, but still go. If the timings work when you’re back then great.

BiscoffByTheSpoon · 03/09/2026 15:13

I think you should decide on the Australia job opportunity separate from what he says or else it puts too much pressure on his answer... Either decide to go for yourself, or don't, based on the job opportunity - but then tell him how you feel once you have decided, and let that be a separate thing.

If he was moving to Australia, and he told you he loved you, would you go out and visit him? Is the Australia move likely to be a permanent one, or just for a few years? Maybe it wouldn't be the end of it.