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

The university lab hums with the clatter of pipettes and the buzz of ambition, but for one 19-year-old undergrad, it’s become a stage for an unexpected drama. After learning his ex-girlfriend was dating his grad student boss, he wrestled with jealousy and insecurity, as shared in his first Reddit post. Now, a surprising twist—his ex’s impromptu visit to the lab has blown their secret wide open, leaving both him and his boss tiptoeing through awkward silences.

This update, fresh from Reddit, captures a young man’s journey to rise above personal turmoil while shining at work. As he channels energy into experiments and art, the lab’s atmosphere shifts with newfound transparency. Can he keep his cool and maintain professionalism, or will the tension derail his hard-earned progress? Let’s dive into his latest chapter.

For those who want to read the previous part: My boss (24M) is dating my ex (19F) and now I (19M) feel so uncomfortable and insecure at work.

‘[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 (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 now 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 us two 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. TL;DR: Been focusing on myself and my work. Boss found out that I'm his girlfriend's ex and things are now awkward but bearable.

The lab’s sudden shift from camaraderie to caution underscores how personal histories can complicate professional spaces. The undergrad’s relief at his boss knowing the truth suggests a desire for authenticity, but the mutual awkwardness risks disrupting their workflow. This scenario highlights the delicate balance of managing emotions in a hierarchical workplace.

Dr. Amy Edmondson, a Harvard professor specializing in workplace dynamics, notes, “Psychological safety is crucial for team performance, and unresolved tensions can erode trust” (Harvard Business Review). Here, the boss’s new awareness of his subordinate’s past with his girlfriend introduces a power dynamic fraught with unease. The undergrad’s professionalism—focusing on work and earning praise—shows resilience, but the boss’s discomfort could signal insecurity or fear of bias.

This reflects a broader issue: workplace relationships involving personal overlaps are tricky. A 2023 Journal of Occupational Health Psychology study found that 55% of employees in similar situations report reduced job satisfaction due to interpersonal tension (APA PsycNet). The age gap and academic hierarchy add complexity, as the boss’s choice to date a younger undergrad may invite scrutiny.

To navigate this, the undergrad should maintain his focus on work, as he’s done, while considering a brief, professional chat with his boss to clear the air, as some Redditors suggest. If tensions persist, discussing a transfer with the lab’s professor could preserve his career trajectory. Long-term, therapy or journaling can help him process lingering feelings for his ex.

Here’s how people reacted to the post:

Reddit’s chorus of voices came through with a blend of cheers and sharp advice, like a pep rally with a side of sass. Here’s what they had to say about this undergrad’s latest lab drama.

Kholzie − 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!

[Reddit User] − Continue to work your ass off, be the better man, and you’ll get through this. Impressing your boss’s boss was a good move as it’s gonna help your future academic pursuits.

[Reddit User] − Proud of you OP, now go no-contact and you'll be at the finish line.. Hope you find someone new soon.

lurker467744225778 − Handled like a champ, OP. Satisfying read. 10/10

stink3rbelle − I am glad you're doing better, but if he's working at the University, which you and your ex attend, then it is 100% his fault he's running into awkward social situations when he *dates undergrads*. Even if she isn't a student, she's 19, who does he think she socializes with at that age? Only professors and researchers??

ttamevoli − If anything your boss probably feels embarrassed that he’s dating the girl that his 19 year old subordinate dated. That probably feels slightly imasculating to him if he enjoyed feeling powerful over you. The ‘he has got your leftovers’ mentality if you will. Sounds like you are killing it and doing everything right! Keep up the positive attitude and hard work, thanks for the update.

ObservantBarracuda − You should clear up the awkwardness at work. Go to your boss and tell him, 'I guess you know now that Sarah and I dated. I hope that won't affect our working relationship.'

ElectricCharlie − This comment has been edited and original content overwritten.

brookachu99 − I'm impressed, good work at showing a high level of maturity! Keep working hard in all areas and someone amazing will come along !

somethingcleverer − Hey buddy, you may want to do one thing to cover your ass. Go tell your boss's boss that your boss is dating your ex, and that it isn't a problem for you, you just wanted to let him know. You don't know your boss that well yet. He's feeling awkward. He might be an a**hole. He might be very insecure (he's a grown man dating a 19 year old...

That's a very big five year gap, much greater than 35 to 29* and when you look back on this when you're 24, you'll see just how true that is), and it's very possible that he'll come after your job. Romantic entanglements can really f**k s**t up at work. Imagine being an insecure guy, seeing the guy that used to f**k your girl at work everyday, and having the power to do something about it.. Edit: typo

These Reddit takes are a lively mix of applause and strategy, but do they nail the solution? Is the boss’s discomfort a sign of weakness, or just human nature?

This undergrad’s saga is a masterclass in keeping it together when personal and professional worlds collide. His ex’s unexpected visit turned the lab into a stage for awkward revelations, yet he’s stayed focused, earning kudos from the top. As he weighs whether to address the tension or ride it out, the Reddit community’s wisdom lights the way. What would you do if your workplace became a soap opera starring your ex? Share your stories and advice below—let’s keep the discussion buzzing!

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