Flirting with Danger



Dear Dharma,

I love your advice and read you religiously! So naturally I turn to you when I find myself in a bit of a situation.

I work in a regular office environment and recently my direct manager got promoted and therefore a co-worker became my department’s manager. Everyone in our team, including me, is happy about all of this.

There’s just one thing. My co-worker – who is now my boss – hit on me. He initiated a kiss and I probably took longer than I should’ve to pull away.

We’ve had a fun flirtatious thing going for a while but I never thought we’d cross that line, especially since I now report to him.

I don’t know what to do. I like him but this is my job we’re talking about.

Flirty and Flustered

Dear Flirty,

Oooh, I wish I knew more!

Like… what do you want to come of any of this?  Do you want to pursue a relationship, or was this just a one-off kiss?

Hmmm, but you did say that the flirtiness has been going on for a while, so there’s a spark there… definitely the possibility of a recurring episode…

Okay, let’s do a whiteboard session.

If there’s the possibility that you both want to pursue something here, then there needs to be a conversation between the two of you to confirm that.

Once you’ve had that conversation, and since dating your boss in secret is not necessarily the best of your options, you need to decide accordingly on the next step.  Is it a conversation with HR, is it moving you to a different department?

Basically, being above board is going to work out for the best no matter how things work out.  I don’t know if your company has policies around workplace relationships, so that’s something you should look into as well.

However, if you know for sure that you don’t want any kind of relationship with your boss other than that of a co-worker, then you may want to consider a discussion of another kind.

Since you clearly don’t feel taken advantage of (between you and me, I think you liiiike him) and there was no abuse of power here, to have a light conversation that acknowledges what happened and concludes with, “We probably shouldn’t let that happen again, since you know, you’re my boss and all…” may not be the worst idea.

I mean – you could ignore the whole thing, but I can almost guarantee if you do, this issue will linger.  And more than likely will happen again.  I just don’t want to see you put yourself in a career limiting position without thinking things through, so be smart, okay?

Please oh please, do come back and let us know what happens!



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1 Comment

  • Irene says:

    Gosh, such great advice. But did the smooch hit happen “before” he was your boss? When I first read this I couldn’t quite determine. Clearly you were both having fun. Maybe he was just “kidding” and evidently “you liked it too”. But to continue is corporate suicide.

    So I’m leaning towards, “it happened before. And we were having such fun!” Now what?

    Time to put on your ‘big girl’ corporate suit and ask for an AM coffee. Tell him in advance what you ‘need’ to discuss (in abbreviated form) so he can also prepare his Coles notes for the ‘relationship’ test. Urge him to bring the eraser, if needed.

    Office relationships in a business environment as per Business Insider says:

    42 percent said they had an ongoing, casual relationship; 36 percent said they had a “random office hookup;” 29 percent had been in a serious, long-term relationship; and 16 percent had met their spouse or partner at work.

    It’s still all a crap shoot. As is life.

Whether you agree with Dharma or think she missed the mark on this one, leave a Comment!

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