Help protect children from gaming harms.

Take our survey

Please or to access all these features

30 days only

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:
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 😊

SevenYellowHammers · 03/09/2026 16:10

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

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.

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.

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.

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!

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.

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.

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.

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

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 😂

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.

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.

WallaceinAnderland · 03/09/2026 16:00

Sparkletastic · 03/09/2026 15:58

Asking him for his thoughts on the potential new job is an excellent suggestion. I’d do that.

He'd come across as very self important if he asked her not to go because of him though. That would put me off to be honest.

eventide13 · 03/09/2026 15:59

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 potentially leaving the country, you have nothing to lose. Tell him!

Tralalalala88 · 03/09/2026 15:59

You could broach the topic gently . I woudn’t launch into “I love you “ just yet . How will you feel if he says he doesn’t feel the same way ? Agree with suggestions of asking him what he thinks of your plans to move

WallaceinAnderland · 03/09/2026 15:59

Think it through. You know nothing about him as an intimate partner. What if he said he was interested, you give up Australia, date for a few months and realise you're not compatible. Then what? You are in the same job with the awkward relationship that you were trying to avoid in the first place. And giving up a great opportunity for yourself too.

Sparkletastic · 03/09/2026 15:58

Asking him for his thoughts on the potential new job is an excellent suggestion. I’d do that.

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.
SquirrelMadness · 03/09/2026 15:57

I wouldn't give up an opportunity to go to Australia for a crush, a man you don't really know that well. You could decide to stay back for him and then he dumps you or cheats on you, or you discover it's just not a great match a couple of months later. So many relationships fizzle out or end some other way in the first few months.

You could tell him how you feel, potentially have some fun, still go to Australia and see how you feel after six months there though. Maybe you'll love what you have out there when more, maybe you'll miss what you left behind here.

I would try to take the crush totally out of the equation and figure out whether the Australia opportunity is something you want to pursue or not. I don't see any reason why you can't give both a try, so long as you're open and honest with him.

Daygloboo · 03/09/2026 15:56

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.

Me and my ex were together 10 years. We were at college yigether but it took us a whole year to actually get together as a vouple So these things do happen..

ThatGladTiger · 03/09/2026 15:54

Jesus woman, just tell him already! Sounds like you both like each other but both too scared to say anything!

Life is too short!

RancidRuby · 03/09/2026 15:54

Go to Australia. Stay in touch with him as friends. Maybe you’ll love it there, maybe even meet someone else and end up staying. Even if you don’t meet someone else your feelings for this guy may change anyway.

If you don’t like it in Australia, or just decide you prefer the UK, or you decide you can’t let this guy go then you can just come home after 6 months, and if you find you do still have feelings for him you can then tell him. 6 months is nothing, I honestly thought you meant you’d been offered a permanent role and it was a stay here forever or move to Australia forever type situation. For a 6 month contract it would be a no brainer for me, I’d be packing my bags.

Lifealwaysgetsbetter · 03/09/2026 15:53

scaredaboutwork · 03/09/2026 15:21

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

Why not ask him for some advice and if you can meet up for a drink…, then tell him about the job and say you’d appreciate his advice as you’re in two minds whether to go. Don’t say it’s because of him! Because it’s really not - you’re in two minds and likely using him as a reason for being in doubt. Once you tell him you’ll know his feelings…

PixieFairySprite · 03/09/2026 15:53

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

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.'

Swipe left for the next trending thread