Wedding Woes

This is why workplace 'entanglements' are a risk.

Dear Prudence,

Several years ago, I accepted a transfer at my company to do my same job in a new city. It was very isolating, and I leaned on my friendship with my older, married colleague “Colin” more than I should have. I had the abrupt realization one day that our friendship had wandered into unhealthy crush territory for me, and also that he was definitely indulging me in what felt like an emotional affair.

I used the feeling of guilt and shame to try and shape my life in a different way—I made a serious effort to join hobby groups and make good friends, threw myself into dating, and generally built a bigger life for myself outside of work. Within two months, I took a job with a different company. I never talked to Colin about this, I just told him I was “busy” every time he contacted me about non-work stuff, blocked his number after-hours, and remained professional but distant when we worked together. He seemed frustrated and annoyed but I just wanted to get out.

Since then, I’ve been loving my new city—I have a social circle I like, a great job, and was recently promoted. I’m in a new, healthy-feeling relationship of about three months. My company is in the final process of hiring a new, specialized employee roughly equal to me, on our team. They invited the team to meet the top three options, and Colin’s name is on the list. How do I handle this? Can I tell my boss somehow? Should I tell my new boyfriend? I’m so ashamed of this and want to leave this guy in the past, not see him every day, but on paper he did nothing wrong.

— This City Ain’t Big Enough

Re: This is why workplace 'entanglements' are a risk.

  • You can tell Colin that you felt things got too personal without saying that you felt like you had an unhealthy crush. 


    You can certainly tell your boss that you previously worked with Colin before leaving your prior company.  

    Ultimately here you need to figure out if YOU are able to put up the professional boundaries that are going to be needed and let this be a lesson that you also can't run away from your problems.  Many career fields are more intimate than you realize and you're likely to run into colleagues from prior jobs again. 
  • First of all, Colin isn't a shoo-in for the job since there's three people in the running.  I'm not recommending sabotaging him, but he's got a 33% chance of even getting the job. 

    Secondly, DO NOT tell your boss anything beyond that you and Colin were colleagues in the past.  There's no reason to bring anything personal into it. 

    Third, yes, tell your partner.  Make the situation clear (you had a crush, never did anything physical, you suspected an emotional affair on his part) and let them ask questions. 

    Finally if Colin gets the job, be professional.  You say you've changed your life and perspective, lean on that.  If Colin asks what happened in the past, you can say, "I realized our relationship wasn't going in the right direction for me.  I apologize if I upset you." or something along those lines.  

    Andplusalso, Colin may decide he doesn't want to work with you if he gets the offer.  Or your company may just not be a good fit for him.  You don't know. 
  • Before Colin is interviewed, note that you know him from a previous role but no don’t tell your boss you had an emotional affair with him. 

    If he gets hired, tell your boyfriend, but also- you’ve worked hard LW to change your life, give yourself credit for that! You made a mistake, you extricated yourself from the situation, and have a whole new great life. Don’t give that away because he may be a colleague again. 
  • Thankfully, the LW's relationship with Colin never developed into a physical one.  There is nothing to tell their boss, other than they previously worked with Colin.  If the boss asks for more info about him, the LW should stick to facts about his skill levels and strengths/weaknesses he would have for the role.

    If Colin gets hired, then tell the b/f about the previous emotional affair.  It couldn't hurt to tell the b/f now if the LW wanted to, I just don't think it's necessary or much to talk about, at this point. 

    As for Colin, if he gets hired, I doubt he would say anything to the LW about their previous pulling back from the friendship.  But, if he does, the LW can give a general, vague statement they felt the friendship was getting too personal.  Or felt they were focusing too much on work and needed to broaden their social circle.

    Upon meeting again, a few casual/friendly sentences to catch back up, should set the right tone for going forward.  Pleasant and polite, but keeping things superficial.
    Wedding Countdown Ticker
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