'I’m secretly in love with my boss and now he is leaving. Do I tell him?' UPDATED 2X
"I’m secretly in love with my boss and now he is leaving. Do I tell him?"
I (29F) have been a teacher at a local school for almost 4 years. I have had a crush on my department head (32M) for the past year or so after we started working more closely. We are both single and have similar interests and view world view points. (It also helps that he is physically 100% my type.)
We also live in a similar area from the school. We have hung out in a group setting outside of school once but mostly he just talks to me in school. We talk about our lives and we vent to each other quite often.
Our county has a STRICT no fraternization policy with directly superior or supervisory employees. He is mine. So I’ve never told him I had feelings because I didn’t want to jeopardize either of our jobs.
Last week, he came to my classroom to tell me he was leaving to teach at a different school 30 minutes away. He said that the school recruited him and that he was very sad to leave but he was excited for the opportunity and pay raise. He said he was going to have to move as well.
That night I went home and had a very vivid dream about he and I being together and going out for a date. I will be stepping into his role next year for the department and I want to be able to reach out to him with questions if I have them.
But I’m worried that I tell him I have these feelings and he doesn’t respond well then I’ve lost him as a colleague and resource. We have our department celebration next week and after that he is gone. So I have until then to decide….. What should I do?
What do you think she should do? Any advice or insight? This is what commenters had to say:
lewisfoto said:
Since he is not leaving to become a priest, I would say you are in the clear. Nothing ventured etc. If he says yes to the date, I might keep it semi-secret for a bit with the coworkers until you are sure it's good for the long term.
ohheysurewhynot said:
Tell him you’d like to take him out for a drink to celebrate his new job, if he’s up for it. Then see what happens :)
Subject-Hedgehog6278 said:
Ask him out!! Make it cute and flirtatious and fun, you have nothing to lose and everything to gain! I've gotten every boyfriend I've ever had by asking them out myself and I highly recommend it. The guys I have dated all loved getting hit on cause it didn't happen for them much. I mean I wouldn't tell him you're in love with him yet of course... But yes ask him out.
Pleasant-Estimate273 said:
Do it and give us an update please!!!
And CSXrodehard said:
I agree with someone else on this thread, ask him out, keep it casual. I would hold back the part about being in love with him, even if he has some feelings for you, for some men it’s a little off putting to know a woman is swimming around the deep end before we even get a toe in the water.
Like the other lady said, make it fun and flirty, and if he already has an interest in you, but never acted on it, trust me that fun date will be rolling around in his mind like a marble in wok when he starts that other job. You’ll know the date worked, if he seems to call you a lot while starting the other job.
She later shared this first update:
We got stuck in meetings all day Tuesday. I had asked him and a PE teacher friend to help me move classrooms and the PE teacher bailed but moved my stuff by himself while I was in my meetings.
Last night we had our department end of year party which he and I were responsible for planning together. He let me know he was getting there a little early so that we could talk but when I showed up some people were already there.
He is pretty private about his personal life at school so we didn’t really get the chance to talk alone. He did mention to me that he had decided not to move and that he was just going to make the commute.
This morning was his last day and we both had some loose ends to tie up so I was running around the school doing that and somehow I lost my phone. I ran into him in the hall looking for it and joked about it. 20 minutes later he came in and said he had found it for me in another classroom.
At our end of year luncheon, he went to say goodbye to our administration and I could tell he was pretty emotionally just about leaving so when he went to say goodbye I just gave him a hug and joked about texting back (he’s bad at replying to text). He said I’ll be sure to respond to you and gave me another big hug.
I’ve decide to let things be for now. He is going through a lot of transition and I’d like to respect that. I’m thinking I’ll give him a few days and then text him to see if he wants to go do something fun. So we shall see… 🤷♀️
She then shared this second update:
One of the things we have mentioned a few times was going to a MLB game together. In the last day of post planning, a friend and I got tickets to a game. We ended up running into him there and hung out for a little while. We somehow even ended up in the same section and had some laughs about “great minds”
I had tickets to go to another game but she will be out of town for it so she gave me the extra ticket. I texted him (first time since he officially left the school) and asked if he was interested in going to the game with me. He has not responded. Its been a few days and he has his read receipts on so he has viewed the text. I’m pretty disappointed but I’ll be alright. Guess that’s it. ✌️