Your Call: Should I Have a Fling with My Long-Distance Boss?

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call on the letter below by leaving your advice in the comments section. 

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Dear Em & Lo,

I recently got out of a 3 1/2 year relationship. For the last year, our sex-life was basically non-existant, so now that I am “free” I am horny as hell.

A couple of weeks ago I got back from a business trip where I met a fascinating guy. He works in another branch of the company and lives 400 miles away, but technically he is my boss/ superior at work. Lots of flirting occurred and was followed up by a heavy make out session on our last evening. However, nothing more happened because I was still in the middle of my breakup.

Since I got back, we have been emailing or texting almost daily, and now he has invited me to come visit him for a few days in summer. He has made it quite clear that he is not the relationship type, needs his space and generally doesn’t do long distance, but that is fine by me. Right now, I am not interested in a relationship and am actually enjoying being “just me” for a while. I just love the way he makes me feel…

Most of me really wants to go and just have an amazing sexy weekend together, but I can’t help thinking that I am playing with fire here. In the fall we will be going abroad on another business trip together for six weeks to work on a project that is very important for my career. Am I being incredibly stupid, putting my career at risk with this fling? What if the chemistry we felt fizzles once we spend some days one on one? Is there a way I can avoid future awkwardness with a pre-emptive conversation? What do I say? “Promise me whatever happens this weekend won’t affect our professional relationship” sounds pretty lame and I doubt it will change anything…. On the other hand, backing out now seems pretty awkward as well, and I’m not sure how to do it elegantly…. 

I don’t feel I can talk to my friends about this because my breakup is so new and everybody loved the ex… Please help me solve this mess!

— Boss or Bail?

What should BoB do? Leave advice for her in the comments section below.




  1. Take it from someone who did shit where they ate… it isn’t pretty when it falls apart. I had a flirty close friendship with my professional mentor (also a doctor in the unit I work in) that turned into a relationship of sorts over time. It ended recently over silly rumors at work that weren’t even true about us. He got paranoid. I got mad at him for being paranoid. It ended in a harsh war of words.

    Yeah… the sex was amazing and I don’t regret falling for him or being friends with him… but I do regret not thinking through the implications of having a workplace relationship. Since it fell apart a month ago, it’s been terrible. We don’t work together but maybe twice a month, but when we do, we have to interact and it’s super awkward. Add to that that a) no one knows we actually had a relationship… b)everyone suspects it…and c)now we must avoid yet act normal around each other.

    That’s really effing hard to do when you’re crying yourself to work and home on the days you work with him. Just don’t do it. Don’t shit where you eat. Not worth the heartache or the potential damage to your career if things go south.

  2. Shitting where you eat is almost never a good idea. This sounded like it might be workable until you mentioned you’ll be working together closely in the future. Not worth the risk, in my opinion. You can find someone to have a flog with who doesn’t work for your company.

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