r/TwoHotTakes 28d ago

I’m secretly in love with my boss and now he is leaving. Do I tell him? Advice Needed

UPDATE 2: 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. ✌️

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… 🤷‍♀️

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?

1.6k Upvotes

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824

u/lewisfoto 28d ago

Since he is not leaving to become a priest, I would say you are in the clear. Nothing ventured etc. If he says yes tot he date, I might keep it semi-secret for a bit with the coworkers until you are sure it's good for the long term.

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u/wttk 27d ago

Pre-school? No, Priest School

12

u/sluttytarot 27d ago

Lol Crazy ex-girlfriend fan?

8

u/wttk 27d ago

Absolutely!

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u/Neonb88 28d ago

I am still on good terms with women I've asked out. It's definitely MORE awkward but sometimes it can even make you closer afterwards

Anyway, for me personally, I definitely do my best to live "you miss 100% of the shots you don't take"

Good luck! I know it can feel scary to put yourself out there, but you deserve good things 🙂

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u/MeetObvious8164 27d ago

Unless you're Fleabag...

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u/BigbyWolf91 27d ago

What if he’s already a secret priest? 🤔

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u/ohheysurewhynot 28d ago

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 :)

37

u/Please_Take_Me_Home 28d ago

This is solid. Casual, but leaves a door open if there needs to be. Also easy for him to decline if not interested in a rather easy way.

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u/Live_Long_And_Suffer 27d ago

Yes, but make it clear it's only the two, who knows if he is naive or not self aware, and will end up inviting and bringing other people together...

6

u/CaliPirate 26d ago

This was my suggestion - let's have a drink to celebrate (birthday), to my sister for a guy who kept smiling and talking to her at work. My sister wasnt sure if he was flirting with her.

They've been married for 10 years, together for 15.

Do it.

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u/FireSignGal_ 27d ago

100% this

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u/roxannewhite2 25d ago

This is the best option for sure!

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u/Subject-Hedgehog6278 28d ago

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 youre in love with him yet of course... But yes ask him out.

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u/zildjianate 27d ago

This is the way. Tbh I probably wouldn't be happily married for 7 years if my wife hadn't asked me out. I was a shy guy who needed a little nudge. She gave me her number and the rest is history.

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u/EthoGuy 27d ago

She asked me out 45 years ago next month. 2 kids and 4 grands later she still has to draw me a picture 🖼️ sometimes.

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u/Gommie5x5 28d ago

Great idea, Hedgehog. OP could even use it as a guise to buy him dinner to say thanks for all the help. Maybe a restaurant near his new job, to emphasize the separation of jobs. Then, she should feel him out and see if there is mutual interest.

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u/Enterprising_otter 28d ago

Guys aren’t this complicated - ‘hey I think you’re sweet, now that we’re not going to be colleagues, would you like to get dinner sometime?’ Doneeee

108

u/CatMilkFountain 28d ago

And make it clear it's a date, we understand zero of most approaches.

42

u/baxtersmalls 27d ago

We’re so used to not being approached that when we are we don’t understand and assume we must be misinterpreting the situation. Definitely make sure he gets that you’re interested, don’t be aloof about it.

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u/Dragon-of-the-Coast 27d ago

Yeah, I had to explain to a friend of mine that, "No, she doesn't actually want help installing software. Show up with wine and flowers."

2

u/Grand-Woodpecker-296 26d ago

Hmm, I wouldn't be so sure but hey, I can also be quite obtuse -

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u/EnemyGod1 28d ago

Neon light billboards are still 50/50 for us.

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u/anonymouscoward689 27d ago

Guys are dumb, trust me OP.

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u/DiffusePenance 27d ago

Guy here - fact check: true

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u/Affectionate_Rise575 27d ago

Also a guy here...I...um...huh?

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u/DontaskemeIdontknow 27d ago

I wouldn't say dumb I would say starved of this kind or approach and indoctrinated that they are potential perverts and shouldn't assume that the girl is interested for fear of being branded a creep or something.

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u/json707 28d ago

This right here.

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u/TheFlyingScotsman60 27d ago

You had me at "you're sweet". Where we going ?? 🙂🙂

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u/ARKweld 28d ago

Feel him out or feel him up?

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u/Yaber2 27d ago

Both, both is good

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u/popcopter 27d ago

I think she should feel him out after she works out he’s interested, not before.

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u/RedditModBot_2 27d ago

Why arent there more people like you. I would love if someone came up and asked me out. I think just about every dude would like this. Itd make life a helluva lot easier lol.

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u/williamblair 27d ago

Men love having a woman be forthright. At the very worst it's flattering as hell, at the best it's what they secretly have been dreaming of.

If they have even half of the easy relationship and commonalities op says they do, it is a slam dunk.

2

u/Ill-Maximum9467 27d ago

This! And if he doesn't accept, he will still always be grateful that you fancied him. He won't hold it against you.

3

u/Subject-Hedgehog6278 27d ago

Totally. Worst case scenario is he is still flattered but just says no, and OP can know that she didn't let him pass by without trying. It could still make his day/week!

2

u/Ethric_The_Mad 27d ago

I would love it if a woman I've been close to for years just came out and said she loved me. I don't think that's something I'll ever experience....

2

u/RevolutionarySell448 26d ago

I've never ended up really dating anyone that I had to pursue first! It's so weird. I gave guys a chance I wasn't really interested in, but when there were guys I had huge interest in, they didn't generally reciprocate, or it didn't go anywhere for very long. I've been married for almost 7 years now, so it was way in the past, but still. I always wondered if I, for the most part, just have shit taste in men or what.

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u/Economy_Homework3869 25d ago

Can confirm, we love when women take innitiative, we are as scared of rejection as anyone.

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u/Pleasant-Estimate273 28d ago

Doo it and give us an update please!!!

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u/PristinePanda2714 28d ago

I lovvve an update story!

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u/dingo1018 27d ago

I got my pocket money on he's gay!

But op seriously go for it, you got at least 2 in's, one is the goodbye drink or lunch, just the 2 of you of course. The other is bringing up the no fratinazing rule, that could be a slam dunk 'y'know that don't apply to us anymore, funny that...' (don't forget to flash your knickers when you swing really high on the swings and share your lollypop)

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u/LetLifeBeLarge 27d ago

How much you got on it

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u/Vell2401 27d ago

You mfs are side betting on this? 🤣

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u/Live_Long_And_Suffer 27d ago

Yes, I'm here for it, we really need an update!

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u/CSXrodehard 28d ago edited 27d ago

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.

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u/LittleSpacemanPyjama 28d ago edited 28d ago

To be clear, and not in a condescending way, I think this is good advice for all, regardless of being male or female. Slow the roll a bit, infatuation is not love and you don’t want to spook your date off, or they’ll throw you like a horse who heard a loud sound. Take it easy, eat some food and drink some drinks and see where things go. Get to know each other in a non-work context and make sure things still feel sparkly. Not to be a downer, I just think that roller coaster feeling is sometimes a bit misleading.

ETA A very natural thing to try is to just ask to go for a drink and talk about his advice for you moving into the role and see how the conversation flows.

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u/little_canuck 28d ago

A very natural thing to try is to just ask to go for a drink and talk about his advice for you moving into the role and see how the conversation flows

This is a good approach.

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u/CursedPaw99 27d ago

and not forget to make it clear it is in fact a date. most men are not very smart in this department (I am a man) and he might think its just a friendly dinner

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u/Ginger-Mint 27d ago

Or coffee.

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u/saramabob 27d ago

My now-husband called his mom on the way to our first date to her know that he was going to meet his future wife (we met online). I’m glad he kept that to himself until much later because there wouldn’t have been a second date otherwise.

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u/Civil-Toe-3010 28d ago

I second this!

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u/floatingisland_jules 27d ago

I am not a fan of pretending something is a work meeting when it's really a date. I've been on the receiving end of this before and it's so awkward. It's much better to suggest drinks to celebrate the new job. That makes it clear that it's a social meeting, not a work meeting.

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u/Exact-Barracuda-8319 27d ago

I think they are saying to have it as a follow-up about work and see if there is anything else there, not as a sneaky date. If he doesn't seem interested in carrying the conversation outside of work boundaries and keeps it professional, then she might have a better idea of whether or not to ask him out on a date.

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u/Ghostbeen3 28d ago

You miss 100% of the shots you don’t take - Michael Scott - Wayne gretsky

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u/AltShortNews 28d ago
  • Ghostbeen3
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u/shewastoday 28d ago

In love? That's a lot for someone who has never dated or hung out one-on-one before. Keep it casual so you don't scare the guy away, and ask to get together outside of work.

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u/JudgeJuryEx78 28d ago

I don't know why this isn't the top comment.

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u/imightbarf 27d ago

Probably because everyone is rooting for her/love coming out on top! We are living in a strange time, and a lot of people just want to hear about things going really well for seemingly nice people who want good things to happen for themselves. Just my thoughts, and have a nice weekend.

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u/EarthInevitable114 27d ago

Strange times indeed. They don't even know her, yet they wish her well.

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u/bitch-i-dont-care 27d ago

I mean that's normal, they're just being nice lol

I do think OP needs to slow her roll. Fantasy does not always translate well to reality.

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u/Neonb88 28d ago

I mean she's known him for awhile.

But yeah OP is definitely building it up in her head

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u/DeskProfessional1312 28d ago

just make it casual and funny... "hey, now that we're not direct employees we can finally go on a date! ha ha ha" and gauge his reaction

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u/DragonScrivner 28d ago

Was coming to say this, yep. Maybe start with a date first if he’s open the idea.

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u/Kabooted27 28d ago

You can find resources anywhere… can you find a partner that checks off everything you want? That is harder to find. I would take my shot 🤷🏻‍♂️

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u/Legitimate_Law2982 28d ago

YTA...if you don't ask him out! I jest, but seriously, a job is temporary, but a possible life partner is forever!

Also, if he is even half the guy you think he is, he will still be there for you as a resource, even if he doesn't have those feelings for you. Go for it!

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u/cbunni666 28d ago

If there are no rules broken, I don't see a problem. Worse that can happen is he doesn't feel the same way. Then you move on.

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u/Unusual_Step_6023 28d ago

Do you really want to spend your whole life wondering what if? Just ask him out at the appropriate time. If he says no, yeah it’ll sting but it won’t suck as much as always wondering what could’ve been.

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u/FinalConsequence70 28d ago

Nothing ventured, nothing gained. Would you rather not, and regret it later? Life's too short. Ask him.

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u/Euphoric_Guarantee83 28d ago

I’d wait until the department celebration when you’re saying your goodbyes. I have a feeling he’s going to ask you out at this exact time anyhow, but if he doesn’t that’s when you make your move - something along the lines of, “Once you get settled into your new place let’s meet up for dinner, you’ll have to tell me how your new job is going.”

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u/Apatow_Powers99 27d ago

I like the idea of giving it till the last bell to shoot your shot. Maybe just outright say that you don't want this to be the last time you see him and let's get coffee or lunch, then see if he tries to make plans. Let's just assume he does feel the same way, one of you is going to have to put yourselves out there. Give him a platform and make it comfortable to take the shot. 🩷

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u/saintstephen66 28d ago

Put yourself out there… go for it!

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u/thealexchamberlain 28d ago

Fortune favors the bold. Ask him out

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u/andmewithoutmytowel 28d ago

Have you considered the possibility that he feels the same way, and that’s why he’s leaving? I’d put my cards on the table.

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u/terraaus 28d ago

I would just say you'd like to keep in touch and let him take it from there.

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u/BurnerMan7 28d ago

Don't tell him about the feelings! That might backfire. Just ask him if he wants to get dinner, now that you're not working together. I bet you'll both be pleasantly surprised what happens :)

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u/CaptCarlos 28d ago

This is the way. You can be subtle about it enough for him to get the message and even if he doesn’t reciprocate those feelings, if he’s a good guy, because you didn’t explicitly say you have feelings for him, he can sweep it under the rug and still be a resource and colleague for you IF worst comes to worst.

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u/sandeecheekz 28d ago

Plz ask him out then come back and update us!! 🥹❤️

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u/Funny_Variety_2170 27d ago

“You aren’t in love with him, he’s just your coworker”

Close proximity attraction is a real thing!

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u/Jenwitha 27d ago

Honestly- shoot your shot! My partner and I met at work.. he wasn’t making the first move so I did only to find out he had quit THAT DAY and no longer worked there.. so I had to be ballsy and find out from a mutual friend if I could have his number ..they had to ask him if it was okay to give out.. turns out it was the best decision of my life.. 10+ years on and a couple kids later.. no risk no reward 😄

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u/Certain_Mobile1088 27d ago

Be casual. Ask him out rather than lay all your feelings on him. That way if he is not interested, you can still be friends. You will need to work on those feelings in that case, but at least you got an answer.

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u/cutecumberwater 28d ago

If you’re still planning to use him as a resource and reach out with questions, don’t do it. It’ll make your job much harder. Maybe take it slow and once he is no longer your boss you can go out for drinks to catch up, and see where it goes from there.

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u/No-Personality-2853 27d ago

What? If they’re both collecting pension checks from the same district it could be awkward as well. Wait til he’s on his deathbed to avoid any awkwardness after.

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u/cutecumberwater 27d ago

Lol ok valid point!!

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u/GrumpyDingo 28d ago

Sounds like the plot of a South Korean Netflix series.

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u/Jessieangel1111 28d ago

This is the chance to make your move since he is leaving and there will be nothing no longer prohibiting you from taking a chance. Give him your number and say that you would like to go for coffee sometime and ask him to reach out if he's open to it

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u/Civil-Toe-3010 28d ago

RUN IT!! Ask him out! You have nothing to lose! If he says no and you do lose him as a colleague/resource (I don't really see that happening), well you seem like a smart person, I think you'll be able to figure it out without him. Don't sell yourself short. But best case scenario you have him as a resource and as a partner 🥲 good luck OP!

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u/trnpke 28d ago

Go for it. Why wonder what have been.

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u/NynaeveAlMeowra 28d ago

Your department head is your boss? I'm not personally aware of any authority that mine has over me and they aren't involved in the evaluation process at all. Huh

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u/Subject_Reality3856 28d ago

Ask the man out. Take a risk! This seems like the perfect opportunity 👌

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u/Familiar-Ending 28d ago

Why not. Practice guys would never peruse a woman in a work environment these days. He very may well have interest as well.

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u/AWalker79 28d ago

Just tell him how you feel and see if he feels the same way or is open to trying something with you. You can also be clear that if he doesn’t reciprocate no hard feelings and would still like to be able to consult with him about your upcoming position.

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u/Rollerdawl 28d ago

Cheering you on! Cant wait to hear the update! 🥰

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u/Locabilly 28d ago

OMG go for it!!

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u/belownormalstandards 28d ago

Shoot your shot

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u/sungazer69 28d ago

He's leaving. Ask him out

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u/alarsonious 28d ago

You're both adults. Tell him how you feel, and if he is not interested, so be it if he can not handle continuing a professional relationship, you dodged a bullet. But since he came to you specifically to tell you this now, he is likely trying to signal that he is interested.

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u/Svelted 28d ago

don't be a fool. shoot your shot. if he rejects you, he's gone. if he reciprocates, you're 30 minutes from your man. do it,

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u/xswifey 28d ago

You only live once! Shoot ya shot!

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u/Effective-Mongoose57 28d ago

Are you both single? If yes, go for it. If he is not interested, you don’t have to worry about seeing him at work, as he is leaving

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u/Slydoggen 27d ago

Girls can ask people out you know..

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u/[deleted] 27d ago

What do you have to lose? Exchange numbers... see what happens.

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u/Publius69420 27d ago

Seriously just ask him out. If he says no just drop it and don’t bring it up again and then only reach out when you have questions about the job. If he says yes, well then win win

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u/Confident_Bobcat_12 27d ago

I would ask him out. If he says no. At least you tried. And you can always include a hey I understand, hopefully we can still be friends and you will be available to help answer questions. I don’t want this to ruin our base as friends statement

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u/Pleasant_Union_426 27d ago

dang just shoot your shot. get his number and tell him you would really like to have lunch with him.

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u/Sultrygoldengoddess 27d ago

Confess! Take your chance before he leaves!

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u/the-dave-9000 27d ago

Go to him!!!!!!!. Throw it all out there. Be prepared for rejection. But I am hopeful it will work out. Incredibly wholesome post and I super wish you well and hope it ends with you both licking each other for life

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u/Lucky_Competition231 27d ago

OP you need to make it happen.

If he rejected you romantically could you handle still being friends?

That’s the question you need to answer.

If you can then there’s nothing to lose.

If he rejects you and doesn’t want to be friends after then that’s a “him” problem and not you.

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u/Kindly_Valuable_1517 27d ago

Yes. He may feel the same way. He just holding back because his position and yours. He's told you that. But remember that old advice. Don't worry about the future and solve today's problem. Please make sure that you want to spend your remaining moon cycles with him. Go with peace and find love.

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u/MundoGoDisWay 27d ago

Ask him out. Would you ever be able to forget it if you didn't?

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u/SleepySuper 27d ago

Nothing ventured, nothing gained.

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u/Silly_Technology_455 27d ago

Ask him out. The worst thing thar could happen is that he says, "no, thanks." Then, you're in basically the same place you started from and not living with regret.

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u/Open-Platform9490 27d ago

You miss 100% of the shots you don’t take.

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u/Far-Piglet4219 24d ago

I bet you dude got a different job to date you.

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u/EarthInevitable114 18d ago

Life anything happens after all this, you better update us here

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u/Standard_Style_5279 6d ago

Awesome that you invited him! Good for you! Sorry the outcome but still.

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u/Late_Breath_2227 28d ago

Closed mouths dont get fed. The worst he can say is no.

DOOOOOOOOOOO ITTTTTTTTTTTTT! Im excited for you (:

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u/bbbritttt 28d ago

This is such a wholesome post please do it!! You got this girl

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u/the_girl_Ross 27d ago

As everyone has said. Ask him to hangout to celebrate his new job, ask for advice about your new position, keep it professional and FRIENDLY! Strictly friendly and only friendly, do not do anything more.

Don't confess your feelings nor your crush. You have only hung out in a group setting once! Jumping in the water, confessing your undying love to someone who is barely your friend (as in you barely know them personally) is straight up off-putting and creepy.

Keep it casual, relax. And stop fantasizing and having insane expectations, it will ruin your chances.

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u/esande2333 28d ago

Yes, yes tell him. Then get back to us

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u/CordeliaJJ 28d ago

Keep it casual, ask him out for dinner or something. Just don't be super akward if he says no or whatever. That way he can still be a resource in the future when you are in the new job.

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u/gto777 28d ago

Ask him out to drinks or something to talk about stepping in the role next year and see what comes from that.

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u/Echo4Ring 28d ago

U won't be working at the same place .. so fraternization won't be a issue

Tell him how you feel. Even if he rejects you. You will still have to deal w him since he's in your city/county

Go for it. That what if will always bother you

What if he gets a new gf while working at that new school ? You would be just friends w him but suffer knowing he's venting about someone else when it could have been you this whole time .

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u/OpportunityCalm6825 28d ago

Tell him, gurl. 😙

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u/zdub2929 28d ago

Send it!

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u/Valuable-Baked 28d ago

Yeah he'll say yes and go on the date with you

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u/gamedrifter 28d ago

Hell yeah! Shoot your shot.

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u/valr1821 28d ago

Go for it and ask him out, but as others noted, best to keep it casual and not reveal just how in love with him you are. In any case, nothing ventured, nothing gained.

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u/NJNiner-4ver 28d ago

Unless you’re hideous..all guys will say yes. Men want sex.very very simply put.

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u/BonerDeploymentDude 28d ago

Tell him, ask him out, let him know. He's probably wondered.

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u/writergal75 28d ago

My vote is ask him out!

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u/Possible_Emergency_9 28d ago

Give him your number, say get in touch since you won't be my supervisor now, maybe we can go for coffee, drinks, dinner, etc. Shoot your shot. At least then you'll know. Don't give yourself the opportunity to live with regret.

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u/JG91215 28d ago

Updateme

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u/Worldly-Promise675 28d ago

Ask him out for coffee or dinner or maybe to an event of mutual interest. Keep us updated!

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u/IlliniChick474 28d ago

It seems there would no longer be a conflict of interest. As others have said, go for it but keep it light and casual. I actually had a similar situation happen but reversed. My first job was at a really small, rural school. At the end of my second year, I was 24 and my principal was 28. He was leaving after that school year and asked me out at a party after school got out. I was not really interested in him in that way, but it was all good! He basically said similar to what other comments have said here...nothing ventured, nothing gained!

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u/[deleted] 28d ago

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u/zsrt13 28d ago

Please do it. You just got one life. Express your feelings irrespective of the outcome. And you won’t lose him as a colleague/frnd even if he says no.

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u/Accomplished_Ad_8013 28d ago

Hes leaving. No conflict of interest. You got this.

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u/SuperSira 28d ago

Do iiiit. You only live once and imagine how much you might regret it down the road if you never try!

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u/nanladu 28d ago

In the end, you regret what you didn't do.

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u/FuknCancer 28d ago

You got a golden ticket there.

" Hey, now that we won't be working together, I would like to go on a date with you"

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u/transat_prof 28d ago

Updateme

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u/mr_etymologist 28d ago

I would be willing to wager that he sought another position because he feels the same and wants a chance with you. I also think he came to tell you because he's hoping you feel the same. Ask him out.

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u/Prestigious-Treat184 28d ago

Shoot your shot! You have nothing to lose

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u/thrwawayboop 28d ago

I need the update when you ask him out AHAH that works out great!!

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u/Plenty_Airline8903 28d ago

But is it worth losing that professional connection? If he doesn’t feel the same, it’s almost certain it’ll end whatever you have going. Love is a strong word too. You don’t really know what he’s like outside of the very work specific relationship. I also feel like men that are interested will give you strong clues.

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u/Yomamaismybabymomma 28d ago

Ask him out and please give us an update!

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u/np8573 28d ago

Ask him out. Communicate your anxiety about wanting to stay colleagues no matter what.

If he's a good guy, he should respect how you feel and hopefully proceed thoughtfully.

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u/Germybrah1 28d ago

Update us

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u/kepsr1 28d ago

Go for it. The worst words in the English language are. “What if”

Updateme!

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u/Allyredhen79 28d ago

Go for it!! Worst case scenario is he says no and you have to figure your job out for yourself.. that’s not too bad and you won’t see him again for a good while, if at all. Or wait until he leaves, see if he’s up for meeting up to catch up about your new role and his, and make your move then?

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u/Flying-lemondrop-476 28d ago

‘colleague’ and ‘resource’ him a while, you might see if he changes his behavior now that HE can act on feelings. The first hurdle you need help with in your new role will be a great excuse to ask about meeting for coffee

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u/Revolutionary_Ad1846 28d ago

Give him a card and in there flirtatiously give him your cell #.

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u/PeachesP59 28d ago

I would ask him out for a date night. Doesn't hurt to try. Not like u have to tell others about it for now. I wish u well. You'll be sorry that u didn't. 🤞🤞

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u/Not-quite-my-tempo- 28d ago

It’s been over a year, how much longer are you gonna wait? Just go for it. There’s a million reasons not to do something.

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u/panteragstk 28d ago

One of three things will happen.

  1. You do nothing, your relationship goes nowhere.

  2. You confess your feelings, your relationship goes nowhere.

  3. You confess your feelings, you now have a relationship.

Do you want to live with regrets or consequences?

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u/Duderoy 28d ago

You have zero to lose. The worst case is he does not feel the same way. Do it. You will regret not doing it for the rest of your life.
"You miss 100% of the shot you take" - Michael Scott.

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u/Sr_Sancho_Panza 28d ago

I am going to venture out and say that he came to your classroom to tell you he was leaving to see how you would react. I’d bet he has a crush on you too

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u/K_Rivera8485 28d ago

Just do it girl. You only live once if he doesn’t feel the same way at least you tried. Just don’t make it weird if he doesn’t share feelings and I’m sure he will have no problem with you reaching out should you need some advice in the future.

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u/miamiphlip 28d ago

Absolutely tell him. You can't win the bets you don't make. You can't make the shots you don't take. Insert whatever other stupid cliché you like, but, yes, tell the man!

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u/gilmoregirl1265 28d ago

Pleaseeeeee ask him out and keep us updated!!

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u/RMT2017 28d ago

When I read that both of you are singles. Gurl... Tell him! Rooting for you

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u/DjuniPerf 28d ago

I feel that most people are reading too far into the title - it sounds like OP has a crush that they don't know what to do with, and the title did its job to nab attention. I doubt OP truly believes they are in love love.

Ask him out to dinner after he leaves. If it goes well, great. If it doesn't, then you are both adults who should be able to navigate a professional relationship instead. Be sure you prepare yourself for either scenario.

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u/writekindofnonsense 28d ago

You have to ask him out. You basically have no choice, You like him, you don't want to always wonder what would have happened.

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u/Rossyact 28d ago

Tell him and update us!!!

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u/Temporary_Hall3996 28d ago

Ask him out to dinner. Give him a card. Maybe along the lines of "maybe we can be friends since you'll no longer be my supervisor." And give him time to think about it.

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u/Leather-Lab8120 28d ago

Wait until he is gone before you declare yoiur devotion.

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u/HelenaValentine 28d ago

TELL HIM or you will always wonder what if?!

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u/idhats 28d ago

I wish just once a woman would ask me out. This is so depressing to read.

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u/burgerman1960 28d ago

Do it! But don’t be weird about it. Just let him know you like him and would like to go out on a date. Can’t hurt anything or break any policies.

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u/SirFomo 28d ago

I think in situations like these you're supposed to steal his dog so you can act like you found it walking around without a leash....or something along those lines

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u/Voidg 28d ago

Doesn't hurt to follow up and say you would like to grab a meal with him.

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u/Suitable-Yak-1284 28d ago

I'm sure you can feel him out to determine if he feels the same or not. GL!

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u/HotAndCold1886 28d ago

Why wouldn't you tell him, or at least hint at it and feel him out? Who knows, maybe he's taking another position because he likes you too!

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u/Leading_Sir_1741 28d ago

Ask him out.

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u/Armada-of-Amulis 28d ago

RemindMe! 30 days

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u/Creative_Work5492 28d ago

RemindMe! 3 Days

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u/BJog_Kittyspoons 28d ago

Go for it.Hes leaving so whats the harm. Tell him you want to take him out for a goodbye drink Go out and have the drink and end the night with goodbye sex

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u/Hank_the_Ranger 28d ago

As others said, ask him to hang out. I'd bet a dinner at the Sizzler he probably has the same thoughts toward you as you do him. But since he was your supervisor, he may be reluctant to ask you lest he be perceived negatively.

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u/Puzzleheaded-Sir7696 28d ago

Ask him out. You’ll regret it if you don’t!

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u/z151z 28d ago

He definitely took the job because he knows it opens a door to a relationship with you.