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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:
Ionlymakejokestodistractmyself · 04/09/2026 23:36

Two separate issues, don't conflate them.

No1: guy you fancy. What if he started dating someone else, how would you feel OP?

If you'd kick yourself for not saying something, bloody do it before he does start seeing someone!

No2: job in Oz. It's only 6 months, don't let a potential relationship make the decision for you. Is it a good career opportunity? If yes I'd take it. If your "boss" has family there maybe you could coordinate a visit from him, as a friend or otherwise!

TeddieBears · 04/09/2026 23:33

Can't advise about Australia but if you meet up regularly just the two of you then next time have some drinks which might help things along. Obviously not too much.

ChilliBassy · 04/09/2026 23:17

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.

He sounds selfless. Like, he's telling you that because he doesn't want to hold you back, but at the same time he's encouraging you to speak up about your feelings, by being indirect regarding 'doubts'. He asked you out on a date and now next week you will go to the theater. Perhaps wear something drop-dead gorgeous? Something which will make him see stars and encourage him to also say what he feels.

If it turns out the feelings are not reciprocated (which I feel they will be! And also have my fingers crossed for you!) - Then you have your Australia answer.

I'd love to know how this turns out. I hope it's a happy ending either way.

PurpleFlower1983 · 04/09/2026 23:04

You definitely have to tell him!

FancyHelper · 04/09/2026 23:00

Tell him how you feel, if ihe doesn’t feel the same head for Australia. You’ll spend your life wondering about what could have been. You have nothing to lose - go for it and best of luck 💖

Wayk · 04/09/2026 22:42

Please tell him. He already asked you out. I love happy ever after stories.

LeopardPants · 04/09/2026 22:41

goldenpanda · 03/09/2026 15:00

You could always take the coward’s way out (not to be sniffed at, it saves face on all fronts) and get a colleague to mention it to him in an omg you can’t tell scaredaboutwork I said this, way.

They can say they know you like him, ask what he thinks and then either way cover with an oh you mustn’t tell her I said anything.

Then if he isn’t interested in you in that way he has already been asked to not mention it and you can just pretend it never happened.

Really? Like a 13 year old would do?!

Just be brave and tell him. You’ll never know otherwise. Life is too short. Oh and if he asked you for a date, surely it’s quite likely he will reciprocate…

ThistleTits · 04/09/2026 22:30

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.

Take the job. Give yourself two years, to settle in. I'm sure there will be loads of people cmg over to visit you.
It's a sliding doors moment. I don't think you should say anything, if you feel the need, just say "is there a connection between us?"
Take it from there.
Good luck, whatever you decide.

MrJoeBangles · 04/09/2026 22:27

WTF??? Wait! Stop! Don't listen to the naysayers. If there is the slightest chance that this is a potential love-of -your-life situation, you HAVE to make your feelings known. It's by far the ONLY way to settle your mind.
It doesn't have to be awkward and it doesn't have to be embarrassing for either party. (And as for the person who said you'd be making a fool of yourself, that's not even a consideration.) We have one life. What's wrong with doing foolish stuff occasionally? Have we become so obsessed with what other people think?
Look, you don't have to bare your soul like some TV drama.
It is VERY, VERY SIMPLE.
Tell him the truth. Go for a drink. Explain your (perfectly natural) fears at this life change. Tell him there are things you will miss. And tell him that he is the thing you will miss the most.
Tell him that you have developed feelings and that you would understand if he didn't feel similarly. (Because you would understand.).
That way you will know for sure.
If it's not to be, you might FEEL a bit foolish but at least you can walk away from it.
I went to work this morning with toothpaste on my face and I didn't know anything about it until I arrived at work. I felt foolish and I have to face the same people on my commute tomorrow!
Just do it!

Papster · 04/09/2026 22:16

One Australia
Lots of men in the world
Go

RocSor · 04/09/2026 22:08

Do that...tell him NOW! Australia decision can wait. Love is everything and everything is love.
I lost the love of my life because I didn't tell him and he was afraid of rejection.

SaucerandCup · 04/09/2026 22:06

Look on the job and the work colleague situation as two very separate things. Take the job- whatever he says. And tell him as soon as possible how you feel- assuming you are happy for you to have to move jobs if you return to the UK.

Sugarnspicenallthingsnaice · 04/09/2026 22:04

Tell him AND go to Australia!

When your 6 months there is coming up for a review you'll have a better idea what you want to do long term.

MabelAnderson · 04/09/2026 22:02

Ask him on a proper date . The worst that could happen is that he says no . That is not so bad ! Sad, but ok. The best is that he is happy and says yes.

Never ask him . The worst that could happen is that you both really care and never know. This seems tragic to me. The best is that he asks you himself.

JJWT · 04/09/2026 21:58

scaredaboutwork · 03/09/2026 14:47

Bit too late by then, surely?

Does he know about the Oz opportunity and if so, what was his reaction to the news that you might be leaving the country?

TheSquareMile · 04/09/2026 21:57

@scaredaboutwork

What kind of job have you been offered in Australia, OP?

flippertygibbet4 · 04/09/2026 21:57

Definitely tell him. You've got nothing to lose. If he doesn't feel the same, well then at least you know. And if he does, then happy days!

On a side note, you don't sound sure about Australia? My feeling about 'amazing opportunities' is that they don't always have to be taken. Just because it's possible, it doesn't mean that you're obliged to do it. Maybe you're happier here regardless of your feelings for your boss?

Whatever you decide to do with your job, you must tell your boss how you feel! We only get one chance to be here, you may as well make it count. Good luck!!!

TravelDad · 04/09/2026 21:52

scaredaboutwork · 03/09/2026 14:57

You say that, but he asked me out on a date a few months ago. I stupidly thought he was joking and laughingly turned it down. Since then we have built the friendship back up. We have plans together for the next few weeks. I think he’s afraid of confessing anything after what happened last time and I’m also afraid. But I’m not sure if I’m misreading the whole thing. Feel so very conflicted.

I have also not accepted the job in Oz yet. I’m torn for various reasons, not just him, but he is probably the main one at this stage.

This is what alcohol was invented for. Sounds like he likes you too but thinks you just want friendship so doesn't want to be rejected again. Maybe ask if he'll miss meeting up with you?

Carouselfish · 04/09/2026 21:49

I say do both. Go and tell him. It's six months. Long distance, all that lovely tension over phone and email and then he can visit midway if it's going well.

Lavenderandsunflowerfields · 04/09/2026 21:48

NestingWorks · 03/09/2026 14:46

I think hand in your notice and see what he does, I’m sure his reaction to that will tell you a lot.

Not if he then decides on not saying anything because she's leaving anyway.
Ask him if he'd like to go on a date and I mean actually say the word date so there's no confusion.
You've got nothing to lose and possibly everything to gain. You don't sound sure about Austrailia anyway.

Jk987 · 04/09/2026 21:40

When are you next going out with him, just you and him? Rather than share your feelings, don’t you both have the urge to get touchy feely as in brushing hands, longer stares etc, then kissing? That’s how things always started with me!

Jk987 · 04/09/2026 21:40

When are you next going out with him, just you and him? Rather than share your feelings, don’t you both have the urge to get touchy feely as in brushing hands, longer stares etc, then kissing? That’s how things always started with me!

SkinnyLatteExtraHotPlease · 04/09/2026 21:38

She got off the plane
Tell him ......

Newbabynewhouse · 04/09/2026 21:38

Yes YES ! Confess... YOLO of course you have to..

GeorginaWilby · 04/09/2026 21:34

He likes you a lot and you like him, so why on earth are you over thinking all of this? Say something dramatic, unforgettable, that you both can tell your children & grandchildren about one day. How about, 'There's only one thing that can stop me from going", then he'll say, 'what's that' and you say, 'You' and that's when you fall into each others arms. The kids will love that, knowing they're the happy ending.

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