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

397 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:
happylittlefruit · 03/09/2026 17:04

Tell him asap. Don't mention anything about Australia yet (too much pressure). Just go on one actual date and see how you feel.

Who cares about the work dynamics, you're already spending time together anyway.

Lentilcakes · 03/09/2026 17:05

I suppose you have to find out if he feels the same way before you go, but I’d def go anyway, what an opportunity - Oz is great (well it was 27 years ago when I went!!). Assume you’ll be working in Sydney or Melbourne (or Perth).

cocoonscriticupgrading · 03/09/2026 17:06

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.

Six months is nothing. It will go by in the blink of an eye. A whole world of new experiences awaits out there. Don't give up on a paid for adventure for a bloke you happen to fancy. These boards are full of relationship problems and whose to say he will stay in the UK forever if he's from the southern hemisphere?

Daygloboo · 03/09/2026 17:06

BillieWiper · 03/09/2026 16:38

That's cool. But they did still ended up being your ex.

I guess I shouldn't make assumptions about his level of interest.

But in my experience once you're an adult with experience you just jump in and shoot your shot.

Yes, what can I say......um....you live and learn ( wink)..

OneTake · 03/09/2026 17:11

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?

If you're going to torture yourself thinking of what if's, just tell him.

Shellityhorn · 03/09/2026 17:12

BlueFahrenheit · 03/09/2026 15:51

Go to Australia.

If he were truly interested, he would have made the necessary moves. Never chase a man.

Edited

But he made the move -- he asked her out! It's not his fault she thought he was joking!

Bzybee · 03/09/2026 17:17

Go to Australia OP, you will be back after your contract finishes. Then, maybe, you can tell him

EspressoWarrior · 03/09/2026 17:17

AppropriateAdult · 03/09/2026 15:46

Oh for goodness’ sake, OP, he’s already asked you out once, and you have ongoing plans to hang out socially outside of work. Of course he fancies you, but it’s up to you to make the next move. Plant one on him after the theatre next week and see where that takes you.

This. I don’t recall ever ‘confessing feelings’ to a bloke until well being the point where we’d accidentally-on-purpose snogged each other.
Engineer a situation where you’re dancing or need to be steadied or something and then just go in for the kill.
My eldest daughter once asked me how I used to pull (not exactly her words) back in the olden days and I admitted I couldn’t actually remember, we probably just jumped on each other at some point.😂 She was horrified!

GreyCarpet · 03/09/2026 17:17

I wouldn't give up an amazing job opportunity for a man...

I can't imagine a man doing so either, tbh.

Piknik · 03/09/2026 17:20

Great that you have the Theatre - you can maybe do a pre or post drink and talk to him then.

In a way, Australia is a gift as it gives you an opening: I've been offered this opportunity but I don't know how I feel about it. Obviously I love my job here, but I also feel conflicted about leaving people behind...

That's enough of an opener for him to pick up if he wanted to, but vague enough to save face if he doesn't.

FancyBlueNewt · 03/09/2026 17:23

I was once a 3rd party in a situation like this. We all worked together. He had a year abroad planned already she told me she really really liked him. I found out he really really liked her. So I organised a night out for a group of us and then mysteriously the rest of us peeled off after a while. They got together, she handed her notice in and went with him on the year abroad and they lived happily ever after.

Annoyedbyhusband · 03/09/2026 17:28

Don’t give up Australia for a relationship that isn’t even a thing yet. Keep in touch with him, invite him to come and visit you and see if he comes. That will be telling, if he feels the same he will come. Then you can decide and who knows.. he might join you.

Itsthewoluff · 03/09/2026 17:30

I’d open a general conversation about how you are not sure about going for x and y reason and then throw in you’ll miss him a lot too. Then go from his reaction.

DrRedT · 03/09/2026 17:36

So similar happened to me, i was leaving the job I was in and going elsewhere, not a different continent though! But given the job, i knew I wouldn’t see this person again.

I had to weigh up which regret would bother me more, not telling them and wondering what if, or telling them and not receiving the response I wanted, I took the first option and sadly didn’t get any response 😂

And as much as it hurt, that’s the easier regret to live with for me.

bellhawk · 03/09/2026 17:38

Just find him and say 'will you go on a date with me before I move to Australia' and take it from there. If he says no, you only have a few months before you're far away from him on the other side of the world.

Miss888 · 03/09/2026 17:43

scaredaboutwork · 03/09/2026 14:46

I am in two minds over the job. On paper it is a fantastic opportunity but I’m afraid about moving so far away, and all alone. I’m very introverted and concerned I’ll be lonely. But the opportunity is a huge one.

Please go. You will always regret it if you don't. I was in your shoes and stayed in the UK. Ended up getting married and kids then he went off and left us all. I could have changed my life but no, stayed for a bloke!
Just go and if you hate it, come back. Stay in contact with him over SM and you never know what could happen, but don't stay for someone who may not even reciprocate!!

Dery · 03/09/2026 17:43

"cocoonscriticupgrading · Today 17:06
scaredaboutwork · Today 15:19
Currently it is six months fixed term. If I enjoy it/they like me they will sponsor a skilled visa for me.
Show quote history
Six months is nothing. It will go by in the blink of an eye. A whole world of new experiences awaits out there. Don't give up on a paid for adventure for a bloke you happen to fancy. These boards are full of relationship problems and whose to say he will stay in the UK forever if he's from the southern hemisphere?"

This with bells on. You would be mad to give up the opportunity in Australia; you say you're in 2 minds because of the social discomfort of going somewhere where you don't know anyone - if anything, that's more reason to go, not less. This is a fabulous opportunity to expand your comfort zone. At 28, you're old enough to know that 6 months will pass in the blink of an eye; so even if you don't like Australia or the opportunity once you're there, it will be over soon enough and on any reckoning you will doubtless have acquired some new life experience. This kind of opportunity is exactly what your 20s are for! You cannot allow a possible new romance to clip your wings.

Separately, I think it is worth mentioning to this man how you feel to avoid the what ifs. I haven't read it for some years now but the Susan Jeffers book, Feel the Fear and Do It Anyway is wonderful for helping you approach situations which take you outside your comfort zone. She also talks about letting go of the outcome. So if you do talk to this man about how you feel, you will have done what you can to move towards to something beyond the platonic. You can't control his response. If he gently lets you down, then you will still know that you did what you could and you don't have to worry about what ifs. If (as seems very possible) he responds more positively, then even better. Either way, it's win/win for you.

I think in some ways the 6 months in Australia relieves some of the pressure. If you're both interested enough, the relationship should be able to survive 6 months in Australia but it also provides a reason not to rush into anything but just to see how things unfold between you.

sonjadog · 03/09/2026 17:46

I might be old and cynical here, but I wouldn't give up a once in a lifetime opportunity for a man you haven't started dating yet. Real life is not a romantic film and there is no guarantee that this guy will be the love of your life if you stay. You may give up this opportunity just to break up with him six weeks' later.

So I say tell him how to feel, if he feels the same he can come out and visit you a few times, you come back, and then if you decide to come back and be in the same place together, it will be on the background of some real experience.

Greatexpect · 03/09/2026 17:46

worldshottestmom · 03/09/2026 16:22

DO NOT, I repeat DO NOT give up the opportunity of a life time for some guy. Please God, don't do it.

Here's the thing, if he really, REALLY liked you you would not be questioning whether he did or not. He would make his feelings known because he would want you off the market.

Do not give up everything for some guy like this, or any for that matter.

Edited

Isn’t love worth more than a job opportunity? Especially when you’re not sure you’d be happy in aus anyway?

OP I would tell him you’re thinking of going.. see what he says

OriginalSkang · 03/09/2026 17:48

Greatexpect · 03/09/2026 17:46

Isn’t love worth more than a job opportunity? Especially when you’re not sure you’d be happy in aus anyway?

OP I would tell him you’re thinking of going.. see what he says

Love is absolutely not worth giving up a good job opportunity for, no!

Pollyanna87 · 03/09/2026 17:48

In the words of Taylor Swift, “My advice is always ruin the friendship”

Gwenna · 03/09/2026 17:54

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?

Go to Australia. Like other PP have said - he’d have made his feelings known by now, in that he’d have tried something. Men aren’t as bothered by external dynamics (in this case boss and subordinate) as much as we think. You’re not his direct report either, so even moreso. If you’re going to Australia, there’s no real future in it anyway unless you’re planning on staying and taking the risk.

Most relationships don’t work out so if you stay and pursue something with him, it may not last and you’ll have drama at your job plus still be in the UK. Your career though - that opportunity sounds like it could decide your life’s trajectory. With plenty of men on it.

It could be a test - how sure are you about Australia? How sure are you about you? Are you going to choose and trust you?

One thing I’ve learned in my life is - you can never go wrong by moving to a new place and new area, with new people. There’s a big world out there. As long as it’s somewhere you know you won’t hate and you are sensible about it, relocation never has failed to be an uplifting reset for me ☀️

Gwenna · 03/09/2026 17:57

Greatexpect · 03/09/2026 17:46

Isn’t love worth more than a job opportunity? Especially when you’re not sure you’d be happy in aus anyway?

OP I would tell him you’re thinking of going.. see what he says

No! 🤦‍♀️🤣 You old romantic you @Greatexpect 🥰

scaredaboutwork · 03/09/2026 17:58

Thank you everyone for the advice. Unfortunately I do not have the time to reply to everyone but I do appreciate it.

A lot of mixed responses - which is what I kind of expected! All different kinds of scenarios racing through my head right now.

For those asking, he does know about the job. I found out that he found out through the grape vine - mutual friends and acquaintances in the industry. It really is a small world. He had been waiting for me to bring it up.

He was a bit conflicted about it. At first said it was amazing, I should do as it’s the right thing for my career and that moving abroad was the best thing he ever did.

But at the same time he said he sensed a lot of doubt in me and if I had doubts I shouldn’t be moving to the other side of the world. In contrast, he said nothing in the world would have stopped him moving to London - he knew that’s what he wanted and nothing could have prevented him making it happen…. that I ought to feel as strongly as that for such a big move.

OP posts:
Gwenna · 03/09/2026 17:59

Dery · 03/09/2026 17:43

"cocoonscriticupgrading · Today 17:06
scaredaboutwork · Today 15:19
Currently it is six months fixed term. If I enjoy it/they like me they will sponsor a skilled visa for me.
Show quote history
Six months is nothing. It will go by in the blink of an eye. A whole world of new experiences awaits out there. Don't give up on a paid for adventure for a bloke you happen to fancy. These boards are full of relationship problems and whose to say he will stay in the UK forever if he's from the southern hemisphere?"

This with bells on. You would be mad to give up the opportunity in Australia; you say you're in 2 minds because of the social discomfort of going somewhere where you don't know anyone - if anything, that's more reason to go, not less. This is a fabulous opportunity to expand your comfort zone. At 28, you're old enough to know that 6 months will pass in the blink of an eye; so even if you don't like Australia or the opportunity once you're there, it will be over soon enough and on any reckoning you will doubtless have acquired some new life experience. This kind of opportunity is exactly what your 20s are for! You cannot allow a possible new romance to clip your wings.

Separately, I think it is worth mentioning to this man how you feel to avoid the what ifs. I haven't read it for some years now but the Susan Jeffers book, Feel the Fear and Do It Anyway is wonderful for helping you approach situations which take you outside your comfort zone. She also talks about letting go of the outcome. So if you do talk to this man about how you feel, you will have done what you can to move towards to something beyond the platonic. You can't control his response. If he gently lets you down, then you will still know that you did what you could and you don't have to worry about what ifs. If (as seems very possible) he responds more positively, then even better. Either way, it's win/win for you.

I think in some ways the 6 months in Australia relieves some of the pressure. If you're both interested enough, the relationship should be able to survive 6 months in Australia but it also provides a reason not to rush into anything but just to see how things unfold between you.

This is great advice @scaredaboutwork from @Dery and I love that Susan Jeffers book, and its sequel - highly recommended!

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