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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:
Aluna · 05/09/2026 11:54

Edamcheese · 05/09/2026 11:44

As an expat myself many yrs ago I have seen many single people coming from all over the world. You will find especially in Australia that you will never be alone. Somehow within the expat community you will get looked after and you will make many wonderful friends. Your only 28 don’t let this opportunity pass you by. It’s not the end of the world if things don’t work out and you come back to uk. You will start again. Take it from me I’m now 79 years and never regretted going and living in many brilliant destinations. Singapore Saudi Shri Lanka Egypt. No one can take these wonderful memories away. There are many more men that you’ll fall for. Just be brave and take the job. Trust me you won’t be alone for long. Don’t overthink things and fret about what iffs. Be brave Good luck.

There are many more travel destinations in the world than there are men one has a meaningful connection with though.

Either way, all she has to do is talk to him. If he’s not interested she can hop off to Aus and enjoy it without looking back.

Matriarchofmenopausemansion · 05/09/2026 12:17

sugarplumlily · 03/09/2026 14:58

You should be more concerned about the what ifs of not going to Australia, than the possibility of something long term working out with a work crush. It is much more likely that when you are older you will look back and kick yourself that you didn’t give Australia a try. It’s the classic deathbed regret. You have no idea who your boss really is. How people present at work has no relevance at all to how they are in a relationship. I’d focus on Australia outside of him. Most men are a disappointment anyway so I’d grab Australia and find a man out there instead. There are thousands of men who will be compatible with you who are you are attracted to. There’s only one Australia.

I’ve lived in Australia. You would be nuts to not grab this opportunity.

This is the correct advice. Very well put. Go to Australia!!

Makingsenseofitall · 05/09/2026 12:38

whatisheupto · 05/09/2026 00:21

Definitely tell him!!
He asked you out on a date for goodness sake! Of course he likes you.
It will be hard adjusting and settling in Oz. It will be much much harder if you're pining after him and wishing you hadn't left and wondering what if... I think it will make it impossible for you to be happy in Oz.

I agree with this!

Jaybail · 05/09/2026 14:28

Talk to him about the job offer, as in, this opportunity has come up, but I don't know how I feel about it, I don't know anyone over there, it's a big step etc. If he says you'd be mad to miss the opportunity he sees you as just a friend. If he says it's a fantastic opportunity but you'll miss your friends, are you sure it's what you want, it's a huge step to make if you're not 100% certain - he wants you to stick around.
If it's the first, you know where you stand. If it's the second you have to work out whether he'd miss you as a friend and colleague or as a soulmate and that requires an honest conversation.
You don't have to pour your heart and soul into it, just say I really enjoy your company and lately I have wondered if we are becoming more than friends. I'm willing to explore that if you are, but if that's not how you see us then that's great too!
Rejection is horrible but I believe you get more pain from what ifs than you do from the truth.

ginasevern · 05/09/2026 15:45

MyrtlethePurpleTurtle · 04/09/2026 18:43

No (real) reason why she can't do both!

Well there is, unless he's able to go to Australia with her. I think the OP would definitely shelve Australia if this bloke said he fancied her. Which I think at her age is foolish. I didn't mean she should never get married in her entire life though.

Dilemma999 · 05/09/2026 16:01

Where you told him you should ‘hang out’ more - I think I’d interpret that as friend zoned. You need to be more explicit.

PoddleOn · 05/09/2026 16:41

I’m probably old and cynical but at 42 I’ve seen so many adventures, plans, hopes and dreams utterly derailed due to a man!
Leave it alone, be brave and go to Australia. If it doesn’t work out, you chalk it down to experience and come home.
You don’t need the added complications, wait for some yummy Ozzy hunk to sweep you off your feet.

ElmBeechOak · 05/09/2026 16:49

I would tell him.

crusader7481 · 05/09/2026 17:00

Notasbigasithink · 03/09/2026 19:03

Do not ruin your chance of a lifetime with your career!
You will meet someone in Australia; its full of men too!

Totally agree - I came to Australia on my own barely out of my teens even though my ex fiancé asked me to stay in UK and get married. I have never regretted my decision and yes I met someone soon after arriving in Australia and have been married over 5 decades.

OP - Do not give up a chance to come down under. If you don’t like it after your 6 month contract is finished then it is easy enough to return to UK. Also if he does have feelings for you he can get into Aus no problem as NZ citizens have a right to reside in Oz under Special Category Visa (subclass 444)
Good Luck OP and do hope you come to the right decision for you.

eatingandeating24 · 05/09/2026 17:02

It's only human to make false moves -- and at 28 you have a lifetime of making false moves!! However, if you do not make this POSSIBLY false move, you'd have a lifetime of wondering "what if". So, be bold and take risk and make that move!! Good luck.

BugOnARugDrinkingTeaFromAMug · Yesterday 09:38

sugarplumlily · 03/09/2026 14:58

You should be more concerned about the what ifs of not going to Australia, than the possibility of something long term working out with a work crush. It is much more likely that when you are older you will look back and kick yourself that you didn’t give Australia a try. It’s the classic deathbed regret. You have no idea who your boss really is. How people present at work has no relevance at all to how they are in a relationship. I’d focus on Australia outside of him. Most men are a disappointment anyway so I’d grab Australia and find a man out there instead. There are thousands of men who will be compatible with you who are you are attracted to. There’s only one Australia.

I’ve lived in Australia. You would be nuts to not grab this opportunity.

Absolutely this!

You are nervous, of course you are but give the job opportunity a chance. If you hate it out there you can come back.

If he says he likes you and you miss out on this chance only for it to all go wrong 3 months down the line it is going to be a massive regret.

Makingsenseofitall · Yesterday 12:41

@scaredaboutworkany update from weekend meet ups at all? Or further thinking ?

Todayismyfavouriteday · Today 01:39

I would confess how I feel about him, but without telling him about the work opportunity in Australia, because that would put too much stress on the possible relationship. I'd tell him: 'I've been thinking about this for a long time, and I feel I have to say this. I'm in love with you, and if you feel the same, I'd be happy to look for another job to pursue a relationship' - you'd be forced to find another job if he says he loves you back (that's the downside). If he says he doesn't, then you can accept the job in Australia with a lighter heart.

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