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Dating a Former Employee

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Mike Franklin


( 7 months ago )

I'm a senior, C level executive at a relatively small company (~75 employees). A while ago, I became very close to a direct report. We began spending more time together outside of work; first in groups in normal work/social situations, but the size of the groups got smaller and smaller until we began spending one on one time together. Poor judgment in retrospect, but we really enjoyed spending time with each other and we were both in a similar place in our lives, both going through the ending of long term relationships. In any event, it all came to a head when the rumor mill inevitably started and we were noticed and questioned. We cooled it immediately and avoided being seen together at work or away from work, though we didn't stop talking altogether, and of course we continued to work together closely for the past year+. Note that our company does not have any kind of anti fraternization or workplace dating policies; something we need, but something that I've been a poor champion of for obvious reasons.

She found a different job; and large parts of why she was looking was to resolve the situation:

  1. it made something of a sensitive workplace dynamic and

  2. if we were ever going to enjoy each other's company outside of work, something we both wanted and discussed, we couldn't work together. It doesn't hurt that her new role is a step up in an exciting new direction for her.

So now here we are. Not to get too far ahead of myself, but I don't want to do this poorly and put either of our careers at too significant a disadvantage. I have no idea what the right way to approach this is with my current workplace, though. Considerations include:

  1. morale among current staff and peers, direct reports and otherwise, some of whom we'd consider mutual friends,
  2. perception of my boss and the board,
  3. a reasonable timeline to avoid the appearance of gross impropriety,
  4. other things....?

If and as we begin dating (which could all become moot if it doesn't work for all the reasons relationships don't work out) I don't exactly intend to take out an ad, but these things have a way of getting out, and I frequently attend industry events that often include an invitation for a spouse or partner. Thoughts? Opinions? Advice? In many things, you find that you're the only one who thinks to care about these things. In many other things, you find that everybody cares beyond all rational reason. This is salacious enough to easily be the latter, though I'm happy to be pleasantly surprised by the former.


Amie Khalifa


( 7 months ago )

I dated someone from work at a similar size company who was senior to me (although I was not a direct report and she was the level below C-level).

When we made our relationship public (shortly before she left that job) we found that almost everyone who had an opinion was really happy for us.

We're married now, and there's no way that the opinion of anyone from that company could ever be more important to me than hers.

Ask her out.

what's your interest