Hi everyone,
For simplicity, here, I’m going to refer to myself in the first person (I’m male), the female subject (27 years old as Y, my daughter (5 years old) as X and her son (6 years old) as Z.
So, I met Person Y around 4 years ago for the very first time. We were working in different departments at the time but it was during a weekend shift and she was one of the only managers on shift so I needed to go see her about something (we’re office based). After I’d spoken to her, all I could think about for the rest of the day was how beautiful she was and how lovely she had seemed.
Same thing happened on a few various occasions over the next year or so.
Then, around a year or so ago (perhaps longer) I was placed in her team, starting a brand new project.
Now this was during covid time and we’d had no interaction for years so I didn’t exactly remember her fully, but I recognised the name and knew I knew her.
And then we met. And I was pretty smitten again. I work from home a lot for personal reasons but have started working in the office more and more just to be near her.
Now, here’s the situation:
I’m single, and have been apart from one or two very short term relationships since I split with my daughter’s (X) mother. I’m 28 years old and in a very good, comfortable place overall. I get on well with X’s mother. X has a few disabilities including being deaf.
Y is 26, single, and has plenty of issues. Z, her 6 year old son is at a new school after the last school weren’t equipped to handle him (they believe he is in the autistic spectrum and are awaiting the lengthy process in this country (the UK) for a diagnosis. His new school is much better but believe after a few weeks he needs to be attending a special measures school, something Y and Z’s father are in agreement with.
This weekend the four of us (X, Y, Z and myself) are supposed to be going out to a children’s event nearby as we thought it would be nice for the kids to spend some time together (they’re never met). This may or may not get cancelled as neither Y nor Z are well at the second.
I have absolutely no ideas whether Y is interested or not. I’ve been told by a trusted colleague that she’d had a lot going on (as I’m already aware of) and that she likely isn’t looking to date right now. When I suggested she was way out of my league, I was told this was rubbish as I’m a lovely person and whilst this could just be her being nice to be, this person is very blunt and tells it how it is.
When I’m work, sometimes, for personal reasons, I sit a short distance away from the team. We occasionally make eye contact that holds for a few seconds and smile at one another.
When I’m say with the team , whenever she walks passes me, she always touches my back, shoulder or arm briefly as she walks by. This could however be due to the fact I’ve been unwell.
We have multiple meeting per week together as I’m currently her second in command (I hate that phrase but if she’s off, I’m in charge, basically. Whilst we do talk about work related things, we spend around 75% of our conversations talking about our personal lives instead and getting to know one another better. I know this is relatively normal in the workplace for people to get to know one another so I’m not reading too much into this.
The problems I’ve got are:
– I think she’s way out of my league
– she has a lot going on in her personal life
-‘I’m getting close to promotion under her tutelage and wouldn’t want to jeopardise this
But basically, I think she’s amazing. She’s the most beautiful person I’ve ever seen, her personality is wonderfully radiant and I just think we’d suit each other well.
As I mentioned earlier she’s not been too well lately so keeps cancelling her days in the office and working from home instead and I keep offering to take her anything she needs or offering support with childcare etc which she has thus far declined but has said she will do if she needs it.
So I guess I’ve got 3 questions I need help with.
1. How do I find out if there is a way to determine whether she’d be interested Interested in me that way?
2. What should my next steps be?
TLDR: major crush on boss, what should I do next?
Thanks in advance!
5 comments
>The problems I’ve got are: – I think she’s way out of my league
Doesn’t really matter what you think. It’s what she thinks that counts.
> – she has a lot going on in her personal life
Not your problem to deal with. People are capable of dating and having a whole life outside of their romantic one.
>-‘I’m getting close to promotion under her tutelage and wouldn’t want to jeopardise this
That IS a problem. I don’t know what the rules and regulations are for colleagues dating, or even superiors and subordinates dating, within your company. It would probably be a good idea to find out, though.
If you got promoted would she still be your boss?
Don’t date someone from where you work.
You said 3 questions but only wrote two…
First: To find out if she is interested in dating, I wouldn’t beat around the bush too much. Because you said she is pretty blunt about those things, so give her all the info she needs. Tell her, that you’d love it if you could spend some more time together. And I know you want this to work out very much, but don’t put that pressure on her. That’s what you’re concerned about, right? Just tell her, that you believe that the two of you would have a good time together. That you would make some fond memories, even if it doesn’t work out. And of course it is fine if she doesn’t have time for this. You want her to be happier because of you and not even more stressed.
Oh and with that i also anwered your second question. Find out how she feels by telling her how you feel, without putting pressure on her. And then the next steps you can discuss with her.
Just don’t do it. She’s your boss.
It’s unethical for her to date a subordinate.
It’s unwise for you to date your boss.