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

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Picture a bustling university research lab, where beakers clink and ideas spark under fluorescent lights. A 19-year-old undergrad, fresh off landing his dream job, feels on top of the world—until a Snapchat story shatters his calm. His ex-girlfriend, once the center of his universe, is now cozying up to his grad student boss, complete with heart emojis. What should’ve been a friendly workplace now feels like a daily gut-punch, as jealousy and insecurity creep in.

This young man’s Reddit post lays bare a whirlwind of emotions—regret, envy, and the sting of seeing his ex move on with someone who seems to have it all. As he grapples with his feelings while trying to keep his hard-earned job, the Reddit community chimes in with advice. Can he find peace in the lab, or will heartbreak derail his professional dreams? Let’s unpack his story and the reactions it sparked.

‘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 damn 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 me and two other undergrads 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**king picture of my boss with a heart emoji. I'm shocked as f**k 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 damn, I felt like someone just stabbed me in the heart. I though I didn't have feelings for 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 s**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 the fact that he's my boss, so he orders me around, just makes me feel shittier 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 s**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?

The OP’s dropped an update on the saga—curious? Click here to check it out!

This young man’s tale of workplace awkwardness is a classic case of unresolved feelings colliding with professional life. Seeing an ex move on, especially with someone in a position of authority, can trigger a cascade of self-doubt and comparison. The undergrad’s shift from friendly banter to silent discomfort shows how personal emotions can seep into work dynamics.

Dr. Susan Krauss Whitbourne, a psychology professor, explains, “Jealousy often stems from perceived threats to self-esteem, particularly when comparing oneself to a rival” (Psychology Today). Here, the undergrad’s boss—older, successful, and now dating his ex—feels like a towering benchmark, amplifying feelings of inadequacy. The age gap (19 vs. 24) and power dynamic further complicate matters, as the boss’s authority at work mirrors his perceived “win” in romance.

This scenario reflects a broader issue: navigating post-breakup emotions in shared spaces. A 2022 study in Frontiers in Psychology found that 62% of young adults struggle with jealousy after seeing an ex with a new partner, often impacting mental health (Frontiers). The undergrad’s regret over “letting her slip” suggests he hasn’t fully processed the breakup.

To move forward, he should focus on self-growth. Journaling or therapy can help process lingering feelings, while setting boundaries—like limiting contact with his ex—can reduce triggers. At work, maintaining professionalism is key; he should aim for polite, minimal interaction with his boss to rebuild comfort. Dating again, as Redditors suggest, could shift his focus to new possibilities.

Let’s dive into the reactions from Reddit:

The Reddit crew jumped in with a mix of tough love and witty one-liners, like a virtual coffee shop debate. Here’s what they had to say about this undergrad’s sticky situation.

[Reddit User] − 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.

[Reddit User] − I think you are looking at it the wrong way. I mean you used to f**k your boss’s girlfriend.

killerqueen5 − 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.

[Reddit User] − I wouldn't let this get you down. He is a total loser. He's 24, and supposedly doing well, but he has to date teenage undergraduate students? Just concentrate on working hard, and you will be fine. You worked hard to land this position and you should not let anyone mess this up. When you are ready, you will find someone else.. Best of luck, OP!

tarandos − One, you should cut off contact with your ex, as you're apparently not over her. Two, this step up thing is nonsense. I know it's very tempting for you to see it like this, but nobody else is. This is just s**tty luck. Would it have been better for you if your ex was in love with a homeless j**kie? I don't think so. Focus on your job. The guy has done nothing bad for you, and how could he? He doesn't even know.. And in my opinion, it's better that it stays that way, or things at work could get really difficult.

ItzSpiffy − Learning experiences like this are frankly what life is all about, but don't think that you could have the same happiness if you could just plop yourself in his place. That's just not how relationships work. It takes two people with two different dynamics to make it happen. You broke up for a reason.

And you're learning things about yourself, things you can do better next time and that's good. It's normal and healthy to second guess but sometimes we just call that self evaluation and self discovery. Just don't take it to the extreme where you're beating yourself up and especially by comparing yourself to him. She's not a prize and he's not a standard.

Don't dwell on what you did wrong or what you're missing out on. You're way too young with sooo much ahead of you for that thinking. Be professional and be friendly. And lastly, it will get easier. Sometimes life just hands you in uncomfortable situations and all we can do is get through them and yes..... Try to learn them. It won't always be so uncomfortable.

coldestmichigan − Man, she's not your problem anymore. You guys broke up for a reason and i can bet my left nut that part of the reason is because of her. She is his problem to deal with now, you shouldn't feel sorry for yourself but feel sorry for him since he's such a great guy. When the day comes when she dumps him, you and your boss can share a beer and bond deeper as colleagues and as jilted lovers.

Floweringpooops − 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 s**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.

shawn0811 − You said that you didn't tell her that he is your boss or that you knew him? So did he know that she was your ex? That would tell me a whole lot more about what kind of person he really is. But if he didn't know, I can understand the situation being awkward, but you shouldn't really be mad at him.

If she was your friend and he was a good dude, then you should try your best to be happy for them(I definitely understand that is easier said than done). The best news about this,is that you are young,and if it didn't work out with your ex then she wasn't perfect. Because noone is. And maybe it will end up being a blessing in disguise and you will be able to find someone who is perfect for you.

Get out there and date around and focus on working your way up. The feelings of jealousy and such will start to fade. And it is very possible that he is just a rebound(since it hasnt been hardly any time at all) and with the age difference they will be incompatible and you can have the 'last laugh' once you find yourself in a successful job amd relationship

_HappyG_ − Dude, this is really tough. The best way to get an ex jealous is to live your life well and be happy, which is what's happening here only you're the ex. She's moved on and living her best life, while you're still holding on to something well and truly over. It's time to get some space from this whole situation and process this breakup properly because you deserve to be happy too.

As for work, if you feel you have the kind of casual relationship where you can chat with your boss about your personal life, I would recommend meeting somewhere private and just explain the situation. Obviously not in terms that would make it seem personal or awkward, but just let him know this breakup hit hard and you'd appreciate discretion and understanding during this difficult time.

You can choose to not go into detail, it's all up to you, but if you leave it unaddressed he'll pick up on the bad attitude and alienation and it won't bode well as a new employee (and could impact future prospects and referrals). These are all short-term goals, but for the long-term you gotta let go of your ex and love yourself. Know that you are worth it and you'll find someone again. You will be okay, and while it hurts now, I can promise you that it does get better.

These Reddit opinions are a spicy blend of humor and wisdom, but do they hit the mark? Is the boss a “loser” for dating younger, or is the undergrad just stuck in his head?

This undergrad’s story is a poignant reminder that heartbreak doesn’t clock out when you punch in at work. His ex’s new romance with his boss has turned his dream job into a daily test of resilience, but the path forward lies in self-focus and professionalism. As he navigates this emotional minefield, the Reddit community’s advice offers a roadmap—let go, level up, and live well. What would you do if your ex started dating your boss? Drop your thoughts and stories below—let’s get the convo rolling!

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

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