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Man finally lands his dream job, finds out his boss is dating his recent ex. UPDATED

Man finally lands his dream job, finds out his boss is dating his recent ex. UPDATED


'My boss (24M) is dating my ex (19F) and now I (19M) feel so uncomfortable and insecure at work.'


My ex and I broke up around four months ago after dating for a little over a year. She was the one who broke up with me but at the time I agreed that it was for the best so we ended things on good terms. We're pretty chill now and we have mutual friends so we often all hang out together. So things between us are chill and friendly.

I work at a research lab at my university and I just recently landed the position after a pretty darn long (and competitive) application/interviewing process. I met my boss, who's a grad student and we became buddies pretty fast. He's a really nice and funny dude that knows what he's doing. I see him everyday since the two other undergrads and I work under him and help with his research while he helps use with our own.

Fast forward about two weeks and I see on my ex's snapchat story a f*cking picture of my boss with a heart emoji. I'm shocked as f*ck so I reply to her story asking her who her new boy is and sure enough she tells me she's dating my boss. I feign happiness for her and I don't tell her that he's my boss or that I know him in any way.

But I really felt like someone just stabbed me in the heart. I though I didn't have feelings for her after our break-up but after seeing her story, I was just hit with a pang of jealousy. Maybe it's because he's a major step-up from me. I'm a poor, disorganized undergrad and and he's a successful, young talent who has his sh*t together.

The next day at work I'm basically on edge the whole day. I would look at my boss, remember that he's dating my ex and just feel so uncomfortable. The rest of the week was like that too. I stopped joking around with him and kind of just stopped talking in general to him. Now I dread seeing him everyday because of the fact that he's my boss.

So, he orders me around, which just makes me feel sh*ttier and more 'below' him. He's got the girl and I've got no one. I still love my job though and I worked so hard to get it so I'm not planning on leaving. I also feel like a sh*tty person since my boss has been nothing less of nice and is honestly, a great guy.

Now I just feel like I should've tried harder in our relationship because damn, she was pretty perfect in every way and I just let is all slip through. The other day, she came over to have lunch with him during his lunch break and I saw them laughing together and yea, another wave of sadness and jealousy. What do I even do now. How do I stop feeling like this? How should I normalize the situation at work?

Here were the top rated comments from readers after this initial post:


it means you have to start dating again and focusing on your stuff. The fact you are jealous it is because you believe they are doing better than you do at this moment. When you start dating again and if your ex-girl still has feeling for you, she would be the one at your position right now.


It sucks but it's moments like these that determine one's character. I know very little about you but I don't take you to be cowardly or petty or someone who wants bad things for others. So it'll be fine and you'll do the right thing.

You feel sh*tty because that's human. But all you can do is take each day at a time and it will get better. And when you're ready to date now you will take the life lesson you learned from all this and not take that girl for granted.

The OP responded here:


yea, that hits pretty close to home.


He is not a step- up from you. I need you to know that people aren't ranked. He is just a person, with achievements and failures and flaws just like you. He's young and maybe not an effective manager. You said he orders you around but try not to take it personally. He sees you as a friend, co worker, subordinate, threat to his relationship, and also probably feels a bit awkward about the situation.

As another poster mentioned, he's dating someone significantly younger. When I was 24, my friends and I would definitely make fun of guys who dated 19 year olds. There's just a huge maturity difference at that age, especially for girls. She's not perfect either and it turns out you weren't right for each other.

You said he's a good guy, and prior to this you were friends. Don't try to be his best bud , but try your best to forgive him and move on. Focus on your work and yourself. You worked so hard to get this job and it sounds like a great thing to have on your resume. It will only make you miserable to dwell on it.

A week later the OP returned with an update.

'UPDATE: My boss (24M) is dating my ex (19F) and now I (19M) feel so uncomfortable and insecure at work.'


Thanks to everyone who gave me advice on my first post. For the past week, I've been trying to focus on myself and my work and not care about my ex and my boss who's dating her. It worked pretty well.

I started a painting and I'm pretty close to finishing it and I impressed my boss' boss (the professor who owns the lab, not the one dating my ex) by staying late for two days in a row to finish a really difficult experiment. During our lab meeting, my boss' boss shouted me out in front of the entire lab and said he was really impressed by my hard-work and dedication. That felt good.

As for the situation with my boss and my ex; he found out. Like I mentioned in my previous post, when my ex told me who her new boyfriend was, I didn't mention that he was my boss so neither of them knew. Two days ago, my boss and us (the two other undergrads) were in a conference room discussing a paper when my ex came in.

She came to drop off my boss's wallet that I think he forgot or something. Anyway, she saw me, did a double-take and went, 'Jaaaake?!'. She was definitely super surprised and caught off-guard and her boss was already like 'wtf' so I was just like, 'heeeyy 'Sarah''. She shot me another shocked wide-eyed look and left. Suffice to say the rest of the meeting was pretty awkward.

The next day, it was obvious that my boss now knew our history. Things just turned so awkward. Like he didn't know how to act around me anymore and what to say. Now we're both awkward around each other. He's still nice and all but things are just uncomfortable between the two of us now.

It's not his fault though. I think that things will get better between the two of us but as of right now, I actually feel kind of relieved that he now knows. Something about how both of us now don't know how to act and what to do kind of makes me feel reassured. 'Sarah' also called me the night that she found out I worked there but I missed her call and forgot to call back.

It's good though, I've been trying to think of her less and distance myself a bit. But if things continue to remain really awkward to the point where both of our work is affected, I'll consider talking to my boss' boss about switching me to work under another grad student instead. But yea, that's about all. Again, thanks for the help guys.

Here were the top rated comments from readers after this latest update:


I am actually sort of glad you didn’t answer your Ex’s phone call or return it. I cannot imagine, for the life of me, any usefulness to that conversation. I mean, did she not know anything about the department you were in at school? Or the likelihood of seeing you if she kept her dating pool there?

IMHO, you really demonstrated an ability to be above drama by not immediately telling your boss or Sara about your previous work/romantic relationship. And i’m super stoked that, instead, you just focused on work and got praised by your boss boss. Good for you!

The OP responded here:


Actually, me too. We're still friends and all but I think I really need to put some distance between us and focus on myself for now. I'm glad I missed the call too. I applied for the job after we broke up and never mentioned it to her so I guess she never found out. Thanks for the support!!


Good on him for holding his sh*t together! It would be horrible if he mouthed off and tanked his future when he's still so young.


As someone who used to be a grad student, a grad student who is dating an undergrad would not be considered as 'having his shit together' or generally looked favorably on by other grad students, lmao. He's also probably poor AF. Still awkward for OP, though.


Oddly enough, no a**holes here. Just a really awkward situation.

So, an awkward situation, but it sounds like they are handling it the best they can. Have you ever had an awkward workplace romance situation? How did you overcome it?

Sources: Reddit,Reddit
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