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Does my boss like me or am I imagining things

Hey guys!

So I’m fairly new at my job but ever since I started and met my boss I got the feeling that there’s something between me and him as cheesy as it sounds.

In our first meeting I mentioned that I have a boyfriend (because I did at the time) to which he replied saying oh I didn’t know you had someone. Even at that point I felt like he meant something by it. It was the way he said it that made me think a little bit.

Anyway fast forward me and my boyfriend broke up a few months ago but no one at my work knows and I am not planning on telling anyone at the same time.

So here’s where I have started to feel that he likes me. He has been joking saying he would like to meet me after work and have more meetings with me. (in a jokey kind of way he is saying this.) Everytime i say something and state an opinion he will go out of his way to incorporate it into work. For example i said i was missing my family. A week later an email was sent out saying work is like family and there’s an initiative to make people feel more at home (an event organised.) He’s always helping me wherever he can and I know he sometimes speaks to my colleagues about me too.

On top of it I have caught him staring at me a lot he will stare intensely into my eyes and recently I saw him checking out my body.

He also seems slightly unsure/ nervous at times around me like he can’t come out and approach me straight out he needs me to look and smile at him and then he does or he will look like he is out of place.

Something else I noticed is when I’m talking to guys at work he will also stare my way to see what’s going on. One time i was speaking to another guy at work and my boss was standing close by and i could see he was trying to listen in on what we were talking about.

He asked one of my colleagues why I wasn’t being my jokey self (I was being more serious with him in our last meeting instead of joking around with him like usual).

Do you guys think he may fancy/ like me or is he just being overly helpful and friendly?

We have a big age difference I’m in my 20s- he’s in his early 40s divorced with kids.

Asking on here what you guys think because it’s work and I would ideally like to do something about it since i like him but also i can’t be wrong about this since it’s work and i know it’ll make things really awkward..
Reply 1
You can usually trust your instincts on these things and it would be pretty typical for a 40 year old divorced guy to be up for it with a 20 year old. You're right though, it has the potential to be messy, particularly with him being your boss, which is a conflict of interest. You might have to declare the ‘relationship’ and look in to changing your reporting line. Personally, looking at it from a distance, I would find someone else nearer your age
(edited 1 year ago)
sounds like he does but be careful as he’s older and in position of power
Reply 3
What is company policy on work relationships? What would you do if you got involved and it caused gossip and resentment or didn't workout?
Original post by Surnia
What is company policy on work relationships? What would you do if you got involved and it caused gossip and resentment or didn't workout?


there isn’t a policy regarding work relationships- is that a good thing ?
Original post by gabriellakhan
sounds like he does but be careful as he’s older and in position of power


That’s hot af tho yh?
Reply 6
Original post by Anonymous
Hey guys!

So I’m fairly new at my job but ever since I started and met my boss I got the feeling that there’s something between me and him as cheesy as it sounds.

In our first meeting I mentioned that I have a boyfriend (because I did at the time) to which he replied saying oh I didn’t know you had someone. Even at that point I felt like he meant something by it. It was the way he said it that made me think a little bit.

Anyway fast forward me and my boyfriend broke up a few months ago but no one at my work knows and I am not planning on telling anyone at the same time.

So here’s where I have started to feel that he likes me. He has been joking saying he would like to meet me after work and have more meetings with me. (in a jokey kind of way he is saying this.) Everytime i say something and state an opinion he will go out of his way to incorporate it into work. For example i said i was missing my family. A week later an email was sent out saying work is like family and there’s an initiative to make people feel more at home (an event organised.) He’s always helping me wherever he can and I know he sometimes speaks to my colleagues about me too.

On top of it I have caught him staring at me a lot he will stare intensely into my eyes and recently I saw him checking out my body.

He also seems slightly unsure/ nervous at times around me like he can’t come out and approach me straight out he needs me to look and smile at him and then he does or he will look like he is out of place.

Something else I noticed is when I’m talking to guys at work he will also stare my way to see what’s going on. One time i was speaking to another guy at work and my boss was standing close by and i could see he was trying to listen in on what we were talking about.

He asked one of my colleagues why I wasn’t being my jokey self (I was being more serious with him in our last meeting instead of joking around with him like usual).

Do you guys think he may fancy/ like me or is he just being overly helpful and friendly?

We have a big age difference I’m in my 20s- he’s in his early 40s divorced with kids.

Asking on here what you guys think because it’s work and I would ideally like to do something about it since i like him but also i can’t be wrong about this since it’s work and i know it’ll make things really awkward..


As earlier, maybe avoid as he is in a position of power. Plenty more fish in the sea without his potential baggage and the fact he has power over you.
Reply 7
Original post by Anonymous
there isn’t a policy regarding work relationships- is that a good thing ?

Not if they are expecting people to use their common sense...
Original post by Cote1
As earlier, maybe avoid as he is in a position of power. Plenty more fish in the sea without his potential baggage and the fact he has power over you.

but i feel awkward about not doing something about it..

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