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

Go to australia. It is great oppirtunity .
Tell him you off to Oz and if he would like to take a holiday there you be happy to see him and show him round.or you could meet thailand . Asia singapore...
It s only 12 monhs.
If something is there he will go out to see you ir arrange to meet in asia and you take it from there.
If he is not interested he will not bother
You are still young no need to change ypur plans and commit to someone who may or may not be intetested

OP, he's your boss and in a position of power, so it really wouldn't be on for him to make a move on you. Plus, you've made it clear in the past that you're 'just friends'. I think he likes you too - no bloke that I know would spend so much time with someone they didn't fancy - and HE ALREADY ASKED YOU OUT FGS! Just be brave - you don't have to profess your undying love for him - just tell him you like him or say how much you enjoy spending time with him or something and see what he says - but I reckon he fancies you too. As for Australia - well god knows! But if you're not jumping at the chance maybe you don't really want to go anyway?

Sounds like limerance/ a crush really. Go to Australia.

In your OP you asked if you might have 'misread' him, but obviously you haven't if he has already asked you out.

You are going to the theatre with him. Of course it's a date. Tell him about Australia which will lead to a very intense final fling type scenario which will be lots of fun. I think you should go to Australia and then you can see how it goes. The initial contract is only 6 months. Tell him how you feel.

Go to Australia.

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

Tell him, not in a a way of I won’t go to Australia if you like me but just generally, you like him, he’s appearing to like you. Would you rather spend the next few months wondering what if and over analysing any meet up/ interaction or just tell him you are developing feeling for him and seee where it goes. He’s likely put off by you laughing off a date so prob sitting at home wondering the same! Be brave, only one life, don’t be regretful !
I had someone like this in my life years ago, I wasn’t brave and he died unexpectedly and I never knew from him what his feelings were, a mutual friend told me he was interested at his funeral and was building up to ask me out etc . Morbid but was glad I knew but regretted those few months could have been much more love filled and he would have known how I had felt. So take the risk!

I'd ask him out for a drink and say there is something you want to ask him about. See if he looks cornered (in which case he has spotted you are keen but isn't himself) or enthusiastic (good sign). Tell him about the job offer and see how he reacts. Tell him you are in two minds about it and value his opinion. See if the possibility of you being on the other side of the world prompts him to show his feelings.

Go out, get drunk, shag him, get on a plane and then work it out from there... if it's meant to be you can make it work if not at least you got a shag!

Does he know about Australia. Even if he likes you, he might out of courtesy not say how he feels for fear of upsetting your plans. So be careful.how you present things to him.

I would, fairly quickly, meet outside of work. Conversation " Tgeoretically Ben, have you ever really fancied any of your work colleagues?' You seem worried about going to Australia anyway so perhaps pass on this for now.

Ok look things are progressing with him anyway. Have a lovely evening at the theatre and give him a peck on the cheek at the end of the evening, at least.

Then the next time you talk you say that especially because of the working together situation, it's important that you and he should clarify with each other where your friendship / relationship is going. Tell him you value his friendship, you'd actually like to be more than friends, if he doesn't feel the same way it's better for you to know this sooner rather than later. Or, don't take that script at all, write your own. But do it. You do it!

And don't bring Australia into that conversation, it complicates things.

This is the best way to know how he feels. His reaction to you saying you are going to Australia will give you the message. Whereabouts in Oz is the job ?

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.

Is he the potential love of your life? Maybe
Is the potential love of your life in Oz? Maybe

He sounds like a good guy, had made his intentions clear and backed off when asked to. If you’re going to have ‘the talk’ with him then let it be about ye and not Australia.

Please don’t move to Australia out of embarrassment either!

You hang out outside of work anyway. Just suggest a plan that is a bit more date like without being a date, get some food, suggest a drink, if he has feelings it will become obvious, I dont think you need to do the physical act of confessing, just set the stage in such a way that if it didn't go as planned you can walk away with your dignity and friendship (or at least work relationship) intact.

This.
But regardless of his response I'd take the job in Oz, I wouldn't turn down a fantastic career opportunity for a new man. If he's interested in you, he'll wait 6 months and realistically one of you is going to have to find a new job anyway.

This would be my view - it’s natural to be ambivalent about a move across the world and if you profess your feelings and he in someway reciprocates, it puts a HUGE amount of pressure on both him and the relationship if you decide to stay because of it. At the moment your feelings may be amplified by the fact that you are wavering about the job, so the intensity of your feelings may be increased or seem stronger than usual because you are looking for an excuse not to go (again - really consider if you would want to place him in that position).

I’d make the decision to go (or not independent of him) and then commit either way - and ask if you can keep in touch as friends. You’re both 28 - young and still finding your feet in life - so you may find once you are in a new job, with a new social network (the expat community in Aus is amazingly welcome, as are the locals!) you’ll find your feelings abate. If they don’t you can confess your feelings from afar - if he reciprocates, you can arrange to meet up/visit, etc and explore it. He may decide a job out there would suit him or you may opt to come back in a couple of years yourself.

I just wouldn't make staying or going contingent on him - you could start seeing each other, it all going pear-shaped and then regret the job opportunity you didn’t take for the rest of your life.

So it's the man's job to make his feelings known, but OP has to think like a man and go to Australia despite her feelings? This makes no sense.
Does he know about the Australia job? If he does, then as others have said, this puts a lot of pressure on a potential relationship. If not, then I agree with others that you should let him know your feelings ASAP... whatever happens or will help clarify things for you in relation to the job.

Besides, he's a Kiwi too. Chances are he's terrified of confessing any feelings he has because he's now convinced she just sees him as a friend after she turned down his date offer. I don't see much to lose if she confesses her feelings but plans to go to Australia anyway - if he likes her enough then they can do long distance, or he can follow her.

Just a thought and may be well off base but it sounds like you're conflicted over the decision to go to Australia. Is it possible you're dwelling on the relationship/possibilities with your colleague and making more of it than you would otherwise because you're looking for a reason not to go? It just seems that if neither of you have found a way to speak about potentially wanting something more or different from the relationship, the dynamic on its own might not be that strong. Imagine that you tell him, he reciprocates, you cancel your plans to go to Australia, one of you finds another job, and you try a relationship - is it likely to endure given that each of you is pretty passive about initiating/pursuing it?

Short answer: right now, I'd focus on your feelings about moving to Australia and make that decision, then figure out where if anywhere this person fits in.

You don't need to tell him about the opportunity in Australia, when you ask him how he feels. I wouldn't. Too much pressure. If you and he do end up together you can tell him down the line.

OK, tell him how you feel. If he doesn't feel the same way and it's awkward you can leave the country. Very handy.

I’d go to Australia. There will be other men.

I think it sounds like you need Australia for you. Trust me, you don't want to spend your life introverted and scared to be alone in a new place. That will give you more from your life than a possible new relationship will. There will be so much more to your life than this one moment, don't miss the op to go and find yourself in a new place and learn who YOU really are and what YOU really like. Australia will give you that. You can always come back, you can't always go. Once you're committed to a relationship you're no longer deciding just for you. So make the most of it!