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

392 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:
SquirrelMadness · 03/09/2026 16:00

MajorProcrastination · 03/09/2026 15:57

I've read too many romance books over the summer.

But my head is saying DON'T LET LOVE LIMIT YOUR OPPORTUNITIES!

My two options:

  1. get everything in motion for Australia, tell him a few weeks before you go. There's a chance for either a face to face "sorry I'm not that into you but I wish you well on your travels" or a face to face "really? I love you too" and a mad passionate fortnight then you leave and either the connection fizzles while you're away or the pull is too strong and he comes out to Oz for a month and you plan your lives wherever or you make it work long distance for a year so at least you've had that experience of living and working abroad, maybe he comes and visits, maybe it's all letters and video calls.
  2. go to Australia without telling him. confess all from the other side of the world like a coward and depending on how its received "oh my God eww, haha, are you joking" gets an "oh how embarrassing! I was so drunk when I sent that, yeah I fancied you but I'm having such an amazing time down under, I'm fighting off the hot men with a stick" or "I wish I'd known, you're the one for me" gets a "let's go halvsies on a plane ticket, come visit me and we'll give it a go" or he ghosts you and it's his loss as you're living in bloody Australia and making the most of your one wild and precious life.

100% this, exactly what I was thinking. Love is so often fickle.

neilyoungismyhero · 03/09/2026 16:00

Why don't you ask him out on a date?
Do you fancy a night out somewhere?
Like you he can either say no or yes..not sure why you turned him down really.

ErlingHaalandsManBun · 03/09/2026 16:02

wishingonastar101 · 03/09/2026 15:49

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!

Actually scrap my advice above. This sounds WAY more fun 😂

WildLeader · 03/09/2026 16:03

scaredaboutwork · 03/09/2026 14:42

Yes, it’s the “what ifs” that are really messing with my head right now. I’ve never felt more torn about anything

Sweetheart @scaredaboutwork you’re 28 years old, this is a huge opportunity for you, what an experience!

planes go both ways too love, if you don’t like it, you can come back!

he’s the boss.. he can get his arse on a plane to see you if that’s what he wants to do.

if your gut feeling is that there are feelings both ways, what have you got to lose by telling him how you feel?

if you’re wrong, you have hardly any time to be cringing, and you don’t necessarily ever have to see him again.

life is short. The world is small. Deep breath and tell him

DeftGoldHedgehog · 03/09/2026 16:05

ErlingHaalandsManBun · 03/09/2026 16:02

Actually scrap my advice above. This sounds WAY more fun 😂

This was basically going to be my advice! Worked with DH.

Contain4 · 03/09/2026 16:06

Are you seriously considering giving up an amazing job opportunity… for a man?!?!

I think you are hoping he wants to date you so then you have an ‘excuse’ not to go.

I think you’ve just got cold feet.

It’s 6 months of your life.
Stay in touch with him when you’re over there and see how you get on.

It’s also not good to mix dating your boss with your job anyway.

Oxo01 · 03/09/2026 16:06

Go but say to him you are going to miss him so much say you want to keep in contact with him and maybe he could come and visit you once settled.

Thebigarsedbitch · 03/09/2026 16:08

This is so Tim and Dawn! Does he know about Australia? If not, I'd just casually mention that you are thinking about applying for a job in Oz, but are still weighing up whether you really want to make such a big move. Ask his advice and gauge his response. If he is interested in you, this could be the time for him to tell you. Just ask him if he'll miss you if you go -say it in such a way that it could be taken as a light hearted comment- and see how he responds. If he says that he will, just reiterate that you are still only thinking about it and could be open to persuasion either way. That gives him an opening to take the conversation further. If he responds with something like 'yes of course I will but it could be a great opportunity..' or something similar you'll know that you are flogging a dead horse. Keep us updated as to the outcome!

Laurmolonlabe · 03/09/2026 16:08

Tell him then go to Australia- it's perfect if he doesn't feel the same way- and if he does you will have to work it out.
You will always regret if if you don't ask, and you will regret it if you turn down Australia.

AnAlpacaForChristmasPleaseSanta · 03/09/2026 16:09

CambiodiNamio · 03/09/2026 14:39

I feel like Richard Curtis may have the answer to this one

But it would involved about 300 misunderstandings, all easily rectified but somehow it never happens and some messages written on cardboard.

BlueFahrenheit · 03/09/2026 16:10

PixieFairySprite · 03/09/2026 15:53

He has already asked her out.

'he asked me out on a date a few months ago. I stupidly thought he was joking and laughingly turned it down.'

And he can do it again.

SevenYellowHammers · 03/09/2026 16:10

“Will you come and stay with me when I moved to Australia?” And watch the reaction.

Amsylou · 03/09/2026 16:11

I would tell him, but not tell him about the job offer in Australia just yet. If he is keen you have a month to see how it goes and decide without putting pressure on him. If he rejects you then off you go and you don’t need to work with him 😊

KnickerlessParsons · 03/09/2026 16:11

Go to Aus, and fall in love with a nice Aussie chap, and put your colleague behind you.
And if it doesn't work out in Aus, come home and find yourself a nice British chap who doesn't have the complications that this one does.

FreddoBRIDGE · 03/09/2026 16:11

Don’t give up the chance of true love for a job. Tell him how you feel and give it a go if he feels the same. If it doesn’t work out there will be loads of other career opportunities ❤️

Kingandqueens · 03/09/2026 16:11

scaredaboutwork · 03/09/2026 14:40

I’m already so torn about moving to Australia as it is. I’m excited for the opportunity but terrified because I don’t know anyone out there. So many mixed emotions!

Don’t move to Australia. Too far from
the rest of the world. I always feel isolated when I visit for holidays.

I think you should express your feelings or you may regret it later, just be careful on how you word it.

HJBeans · 03/09/2026 16:12

Don’t miss out on opportunities at your age - you will never again have the freedom to explore places, people and yourself as much as you do right now.

Do let him know how you feel. If he asked you out previously it obviously won’t be unwelcome. Why are you doubting this?

But then also DO definitely go to Australia regardless. 6 months is not too long and if it starts well between you he could come visit.

Moreover 6 months is not too long for you to come back home after if you hate it there. The opportunity sounds amazing and the ‘what ifs’ if you don’t try it will be huge. Honestly, just do it.

And then you can tell him you’re going but that in thinking it through you realised how much you’d miss him and let the conversation go from there.

Kidsandhouse · 03/09/2026 16:13

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? "

I love this idea!

Waytoohothot · 03/09/2026 16:13

I think you are living in some type of fantasy world, you have a job in OZ but do you want to stay or live there? Its costs at least £20000 to get residency, if you tell him you like him the best you will get is a s**g, do you think he will say stay and marry me or i will come with you,

AmazonAntiqueStore · 03/09/2026 16:14

Kingandqueens · 03/09/2026 16:11

Don’t move to Australia. Too far from
the rest of the world. I always feel isolated when I visit for holidays.

I think you should express your feelings or you may regret it later, just be careful on how you word it.

Millions of Australians seem to manage just fine.

It’s for six months initially anyway. If OP doesn’t like it she can always come home.

HJBeans · 03/09/2026 16:14

FreddoBRIDGE · 03/09/2026 16:11

Don’t give up the chance of true love for a job. Tell him how you feel and give it a go if he feels the same. If it doesn’t work out there will be loads of other career opportunities ❤️

Is it true love if it can’t manage a six month separation, though? You learn so much about yourself living somewhere else for a bit and it’s an amazing opportunity to develop her career, not just a one-off job.

FreddoBRIDGE · 03/09/2026 16:18

HJBeans · 03/09/2026 16:14

Is it true love if it can’t manage a six month separation, though? You learn so much about yourself living somewhere else for a bit and it’s an amazing opportunity to develop her career, not just a one-off job.

I missed the fact that it is only for six months. In that case, tell him how you feel and have a long distance relationship til you come back or he joins you out there. Love is so much more important than careers in the end.

HorseandHeron · 03/09/2026 16:20

FreddoBRIDGE · 03/09/2026 16:11

Don’t give up the chance of true love for a job. Tell him how you feel and give it a go if he feels the same. If it doesn’t work out there will be loads of other career opportunities ❤️

If it was true love, do you not think he'd have made it clear that he was interested by now? I think the opposite - don't give up the career-adventure-of-a-lifetime on the offchance that some bloke you work with might fancy you even if he has never made a move.

eventide13 · 03/09/2026 16:20

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?

  1. Tell him
  2. Go to Australia
  3. If he feels the same, he can come visit and you can do long distance for 6 months. If he doesn't feel the same, you don't have to see him again!
PixieFairySprite · 03/09/2026 16:20

BlueFahrenheit · 03/09/2026 16:10

And he can do it again.

Why should it come from him?

Women should feel equally as confident asking a man out.

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