Should you date your boss: part two

Should you date your boss?

‘It’ll be OK’, I told myself, to dismiss my instinctual consternation (when the question should you date your boss arose). I wilfully entered into this daily contract of self-delusion (telling myself things would be okay). And, for a short time, they were.

The outcast

When co-workers found out, the secret/relationship became public property. Initially accepting, over time, bitterness and distrust entered the fray. I wasn’t accepted within my peer group anymore (despite sharing the same job title) and yet I was still the subject of a professional hierarchy. Alienated from peers and within my working environment, I grew lonely. And paranoid.

No longer could I talk to co-workers/friends about my partner/personal life, which meant they felt they couldn’t confide in me. Despite the rules we mutually set down, pillow talk inevitably lead to work talk, and discretion went out the window. Colleagues grew suspicious and/or supercilious in my company, fearful that our boss may make decisions or judgments based on my personal feelings (towards them). I was a conversation-killer: they stopped when I entered a room. Everyone needs to vent frustration (about their job and boss), but I had no one I could let off steam with – and people no longer felt secure doing this in my company. Our close-knit team was fractured and my friends no longer trusted me.


As an ambitious girl who enjoyed her job, thoughts of losing a promotion or never gaining greater responsibility – because co-workers might interpret praise or any behaviour as suspicious/favouritism – informed a growing sense of bitterness and frustration. My relationship had placed all footholds on the career ladder out of reach.

I hadn’t considered myself a jealous or envious person – they were traits I abhorred. Yet, when paranoid and forced to suppress emotion, all kinds of unpleasant, unfamiliar behaviour surfaced (which took a bite out of my self-esteem).

Pre-relationship, I’d felt the boss had his favourites – female peers he’d joke with and defer to regularly – and that was okay; these co-workers were my friends. Now, their working dynamic stung (and gradually poisoned my friendships). I started to act unprofessionally: monosyllabic and rude when spoken to, flirting inappropriately with male co-workers, internally seething with hurt and anger. Understandably my boss/partner didn’t find this behaviour attractive, and our relationship swiftly and messily disintegrated (before everyone’s eyes).

Should you date your boss: starting over

However your relationship with your boss plays out, over time your ambitions and sense of self will be undermined. It’s almost impossible to separate personal and professional relationships; but should your union succeed, it will, at some point, cause a conflict of interests that will impact on your relationship. Career progression, a new working environment and a clean slate will suddenly seem very appealing.
I couldn’t continue to see my boss/ex (at work) everyday. Using him as referee (and lying when asked why I’d left my previous position) I found new employment. I regret having to leave; it was the most enjoyable job I’ve had. can connect you to over 3.5 million singles in the UK and with our blog you don't have to go far to get the best dating advice on the interweb!

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