Although I researched the employer before applying, it wasn’t until after I was called to interview that I noticed the name of their newly appointed VP (my would-be boss) as a person I know. I met him nine years ago at a work conference while in my mid-20s. Regrettably, we had a brief affair, despite his being married and long distance from me. The affair lasted one summer over maybe 2-3 encounters. I put an end to it but we remained in regular contact by email for another year during which I tried to transition us into a friendship. But because he remained in his marriage, I think I became the “path not taken” and he struggled to move on.
At a conference later that year, I saw him in person and he had a minor meltdown, lamenting that it didn’t work between us and hating that I had moved on to date others. Since then, over the years, he’s occasionally emailed me and has always been friendly and appropriate (if a bit wistful). He remained married and now has children as well.
I emailed him after I discovered the connection to this job and he was friendly and said he was willing to work together. Still, I sense a tone in wistfulness and nostalgia in his email. I have no doubts in my own ability to redefine our relationship as a working one. I have always admired him as a professional. But one’s relationship with one’s boss is a critical one and I have this nagging suspicion that he still holds a torch for me, crazy as it sounds. If I am offered this job, is it reasonable to think that he can put any old feelings aside so that we can work together? Or would I be foolishly placing myself into a difficult working environment? — Water Under the Bridge
This is really a tough situation, and one in which only very careful consideration will lead you to the right choice. I would start, first, with discussing the issue with your boyfriend. If he’s going to move across the country with you as you pursue this job, he deserves to know about whatever romantic/sexual history you have with your boss and your anxiety around that history. Including him as much as you can in your decision is not only appropriate, it’s good practice for sharing a future together. Bottom line: if you don’t tell him about your history with your boss and it comes out later, after you two have moved across the country, there’s potential for a lot of pain and tension. He’ll wonder why you kept it a secret from him and whether he can trust you.
The next thing you’ll want to do is get as much information about your potential work culture as possible. Would you be working in the same office as your boss? Interacting with him on a daily basis? How many other employees does he supervise? If there’s a chance for you to have a follow-up interview in-person, that would be ideal as it would give you not only a chance to ask these questions, but to see your would-be boss/ex-fling (I’m assuming that the reason you didn’t see him at your first in-person interview is because he hadn’t yet started?). If I were you, I’d even request one more in-person meeting before accepting the position so that you can meet with your potential boss and assess the situation.
Your gut will tell you much of what you need to know upon seeing him again. Please do try to make this happen before accepting a job as his subordinate — even if you have to pay your own expenses to fly out there. If your potential employers see no reason to interview/see you again, you can always say that you’ll be in the area looking at homes/apartments and would they mind getting together for a lunch while you’re there (make sure the ex-fling is included!). As much time and money as this may cost you, it will be worth it before making such a crucial decision.
Finally, if you’ve done all of these things and you’re still unsure what the right move is, then consider what the best case scenario versus the worst case scenario would be if you took the job and which one would have the greatest impact — good or bad — in your life. Make a “pro” list of all the things you hope this “dream job” would provide you. Then make a “con” list of all your fears, including the affect it could have on your relationship. Since you can’t possibly look into the future and know what’s going to happen, you have to be wise and decide whether the potential cons are worth the risk of the potential pros. If the answer is “no,” then you’ll know what to do. Good luck!
*If you have a relationship/dating question I can help answer, send me your letters at email@example.com.