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Relationships

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Head over heels for a colleague. Is this a disaster in the making?

36 replies

skininthegame9 · 17/07/2026 18:26

New profile. My head's all over the place at the minute, sorry for the detail.

I joined a new workplace six months ago. Got on well enough with everyone. One day out of the blue, a male colleague confided in me he was struggling with mental health. I don't have a background in that so I don't know why he chose me out of all the familiar faces, but I was there for him. Over time, he shared more and more and oddly, rather than feel uncomfortable, I became happier that he was trusting me over others. I wanted to look after him. We bonded more and became friends. I fancied him a bit, but didn't make any advances - not the place.

Last month we went on a work's do and, out of nowhere, we kissed. I was drunk, he was sober as he was driving.

He said the day after he enjoyed it.

We went out again a few weeks after, just us two after work as friends. We kissed again. We've kissed since.

I sent him a text and said I've developed feelings for him. He's also admitted he has feelings for me, so it's not one sided. In person after, he said he wants to try and make it work but he's got various reservations. Main one being it's a family run company. His family. Relatives work alongside us and are in senior management roles. He isn't senior.

Since then we've agreed not to use the word "relationship" and we've not broadcasted anything, but agree we're closer than friends. He brushes his hand against my leg, we go for a hug in an empty room when we're struggling, he's sent me a nude (I consented). I stayed the night at his once. This isn't just friends.

I've fallen completely in love with him but just last night, despite all the above, he finally said he wasn't sure if it will work, mainly because of work optics and the age gap. And said that if it didn't work out it'd be a disaster with us still being at work together. He doesn't want to lead me on and hurt me later.

Terrified. What do I do here? We're both single before anyone wonders.

OP posts:
MakingPlans2025 · 17/07/2026 18:28

What is the age gap - this is a critical factor.
(also don’t do anything physical on work premises you could both get sacked)

skininthegame9 · 17/07/2026 18:31

MakingPlans2025 · 17/07/2026 18:28

What is the age gap - this is a critical factor.
(also don’t do anything physical on work premises you could both get sacked)

So sorry i forgot to say. I'm 29 he's 41. He's worried how that looks.

OP posts:
BlackBean2023 · 17/07/2026 18:33

I think he’s letting you down gently OP as he knows you’ve caught feelings. 💐

NoCommentingFromNowOn · 17/07/2026 18:36

Even though he’s not senior, it’s his family company. You could lose your job if he wanted it, he has all the power here.

I’d be so very very careful to be honest.

LetGoLetThem1234 · 17/07/2026 18:36

One of you will need to leave the current workplace if you both decide that you want to continue the dalliance.

Not sure how convenient or possible it is especially given the current job market for most professions/industries

Arlanymor · 17/07/2026 18:39

You accept what he has told you - it won’t work for a million reasons. No one struggles at work and needs a clinch in the stationery cupboard. It was short and fleeting. Move on.

Megifer · 17/07/2026 18:43

What are you terrified of? Just chalk it up to a bit of fun at the time and let it go. This doesn't need to be a big deal for anyone.

TFImBackIn · 17/07/2026 18:48

This really isn't going to work, OP. He's 41 and doesn't dare tell his family that he's seeing you? I'd look for a job elsewhere and I'd also look for someone my own age who had a spine.

TeaIsLovely · 17/07/2026 18:54

You need to leave the company - and then see if it works out between you.

Andshesoffatatrot · 17/07/2026 18:56

No it’s not just friends, but it sounds like he’s doing a number on you. Are you sure he’s single?

Necessarync21 · 17/07/2026 19:04

NC for this because outing. Similar age gap, but we were both a bit younger. I got together with the “big boss” at work, we are still happily married, decades later. It wasn’t his family company though so maybe that makes a difference? Our work weren’t happy but when they realised we actually worked really well together it was fine.

skininthegame9 · 17/07/2026 19:22

He's definitely single, other people have said as much. He told me he's never had a long term relationship apparently and doing it with "the new girl twelve years younger" looks terrible even if he does love me. Obviously haven't asked colleagues to verify the relationship history!!

OP posts:
Arlanymor · 17/07/2026 19:23

He's said won't work - walk away with your dignity intact.

BeeCucumber · 17/07/2026 19:25

Yes. Leave and take your dignity with you.

MissAmbrosia · 17/07/2026 19:27

Sounds like he's playing with you. Walk away.

IdaGlossop · 17/07/2026 19:29

No long-term relationship at 41 is a bit concerning. Relationships at work have always been a big no for me, despite extreme temptation in one case. Don't jeopardise your financial independence!

HundredMilesAnHour · 17/07/2026 19:36

I think this has car crash all over it. I wonder if he has history of making moves on the new girls at work and that’s why he’s not willing to even use the word relationship or admit you might be dating. Add that to the age gap, his family owning the business and his (alleged) lack of relationship history, do you really want to hang around being treated like his dirty little secret?

You deserve better.

Overtheatlantic · 17/07/2026 19:42

He doesn’t love you; he’s telling you to walk away. Leave the company and nurse your wounds.

whippersnapper55 · 17/07/2026 20:01

I don't think he sounds like a keeper to be honest. He was struggling with his mental health and you wanted to look after him? That is not a good basis for a relationship. He's never had a long term relationship at 41? Big red flag in my opinion. And then there's the fallout at work - if you break up, he's not leaving is he? If it's his family firm! So he would probably make it too uncomfortable and awkward for you to stay.

Walk away from this one, it's way too much trouble and he doesn't sound like he's in it for the long haul.

Aligirlbear · 17/07/2026 20:18

Based on your need to go into an empty room for a hug when you are struggling and the brushing of hands against legs you can bet that more than one person has noticed and people are speculating / know. Sorry but in the environment you are describing it has disaster written all over it. If you want to continue one of you has to leave and get a new job. As he is a relative of the owners it won’t be him having to move .

Personally I would put this down to a dalliance / fling , let him go and get on with your life. What will happen if this goes on for months and then ends ? It will be very difficult to continue in the business and one will have to leave ………..

sunnydayyzz · 17/07/2026 20:25

No long term relationships and poor mental health? His got red flags coming out his ears and you should run a mile.

Random321 · 17/07/2026 20:53

Well I can see why he's not in senior management! He's clearly not the wisest.

His opens with his mental health issue.
He is 41 with no proper relationship history.
Has put his family/employers and his job at huge risk of a sexual harrassment claim.
Nude photos to a much younger colleague.
He thinks nude photos work on mature women?!
Is he actually employable elsewhere or is it a family favour? I ask becsuse he sounds like a total liability in any workplace.
He doesn't have the balls to declare it at work.
He doesn't have enough respect for you to be open about it.

You also don't seem the wisest.
6 months in a few job being this isn't the best move and you've also overlooked so many red flags.

EverMissWicklowSometimes · 17/07/2026 20:58

One day out of the blue, a male colleague confided in me he was struggling with mental health. I don't have a background in that so I don't know why he chose me out of all the familiar faces, but I was there for him.

This part is a massive red flag. You don't speak to a colleague you barely know about your mental health problems unless you are trying to manipulate them.

TreesAtSea · 17/07/2026 21:12

Random321 · 17/07/2026 20:53

Well I can see why he's not in senior management! He's clearly not the wisest.

His opens with his mental health issue.
He is 41 with no proper relationship history.
Has put his family/employers and his job at huge risk of a sexual harrassment claim.
Nude photos to a much younger colleague.
He thinks nude photos work on mature women?!
Is he actually employable elsewhere or is it a family favour? I ask becsuse he sounds like a total liability in any workplace.
He doesn't have the balls to declare it at work.
He doesn't have enough respect for you to be open about it.

You also don't seem the wisest.
6 months in a few job being this isn't the best move and you've also overlooked so many red flags.

Yep, this just about covers it.

CamillaMcCauley · 17/07/2026 21:13

I’ll bet this isn’t the first time he’s cracked onto the naive young hire at work.

He’s basically a pile of red flags in a trench coat and you’re probably going to have to look for a new job when this inevitably goes south.