A reader writes:

I’ve been trying to break into a niche industry (30-40 jobs in a city with a population of 3 million) for a while now. I’m in my late 20s, and though it took me some time to decide what I wanted to do with my life, I have finished my degree and completed two internships. I’m working part-time in a related field and freelancing while searching for a full-time job in the niche industry. I’m willing to move for the right job, but I’d rather stay close to home — so I was stoked last summer when I got an interview for one of the very few entry-level jobs available in my city! I ultimately didn’t get it, but the interview went well enough they encouraged me to apply the next time they had an opening.

Then an acquaintance who works at the company called me up and asked if I wanted to get coffee. I figured she’d offer me tips on how to do better next time. Instead, she told me to give up on ever being hired there — turns out, a girl I had gone to high school with is a real rock star at this company, and she threatened to resign when it looked like I was about to be offered a job. (I hadn’t realized it was her because her married name is different.) I’ll be honest — I wasn’t a very nice person back then, and I probably was pretty awful to this girl. I looked my former classmate up, and her resume really is incredible. She graduated from college early and has awards people who’ve worked in our industry twice as long haven’t won. Her public-facing work is top-notch. I’m guessing she’s the kind of employee a manager wants to keep around.

My acquaintance’s prediction appears to be true: I didn’t get an interview for a new position at the company that would’ve been an even better fit than the one I’d interviewed for. When I asked why, I was told a staffer had raised some concerns and the company would not be moving forward with my candidacy. I’m heartbroken. I worked so hard for so long to get the training required for this type of work, and I don’t think I deserve to be blacklisted for something I said when I was 17. I have my former classmate’s work email. Should I beg for forgiveness?

This is tricky.

On one hand, I don’t think there’s anything to lose by apologizing. And if you were pretty awful to her, it sounds like it would be the right thing to do.

On the other hand, it’s going to look motivated by your desire to get a job there, and risks coming across as more self-interested than genuine.

Because of that, I think you should do it only if you can frame it as a genuine apology, unconnected to your job prospects there. If you can explain that the situation made you reflect on your behavior to her in high school and realize that you owe her an apology — and if you can honestly say that you don’t expect this to change anything about your job prospects there but just genuinely wanted to apologize — then maybe.

However, if you then apply for jobs there again anytime in the next year or two, it’s likely to look like it wasn’t that genuine.

So … I would say to send that type of apology because it’s the right thing to do but also to write this company off for at least a while.

Now, is that fair that you’d be blacklisted for something you did at 17? I think it depends on exactly how bad your treatment of her was — there are some things that would be bad enough that you shouldn’t expect it to be written off even a decade later. And there are other things where holding a professional grudge after someone expressed sincere regret would be an overreaction.

But this might not be about a grudge. She might genuinely feel that she can’t comfortably work with you. It might not have to do with forgiving or not forgiving you, and she might be well aware that you’re a different person now — and yet might still feel that seeing her high school tormenter every day isn’t something she’d want to stick around for. If that’s how she feels, that’s legitimate — and it’s understandable that her employer wouldn’t want to lose a stellar employee for someone who’s an unknown quantity.

Ultimately, it’s not so much about whether it’s fair (it might be, it might not be), but about what is and how you respond to that. I think sending a genuine apology and then moving on from this company is your best move here, as frustrating as I’m sure that is.