Should you date your boss: Part One

Should you date your boss

For seven months, dating the boss was my reality. It may have been a proximity-based crush due to spending long hours working to tight deadlines together – in pressured environments you can quickly start to depend on and appreciate those whose banter or sense of calm helps defuse stress. It may simply have been genuine romantic affection – he was attractive and smart, fun and kind. Whatever the reasons, if asked today, should you date your boss? I would answer: no, not if you enjoy your job.

An effective and fair leader/boss makes their team want to work hard for them, want to curry favour; and someone you admire, who also happens to wield their power lightly, is an intoxicating prospect. So, yes, it’s easy to confuse good working rapport and camaraderie with romantic affection – and potential. And once this line is blurred, inevitably, you find yourself thinking, ‘we make a really good team. I always look forward to seeing him. I wonder?‘ Then, seriously considering, should you date your boss? I know from experience that once you allow yourself to think in these terms, you’re opening an emotional Pandora’s box that’s very difficult to close (without collateral damage).


Many companies have policies about staff relationships, but this was a tiny start-up company staffed by a tight group of young individuals, many of whom mixed socially. We worked long hours; we shared an eager sense of team responsibility and ambition.

The relationship began during after-work drinks. We flirted, texted the next day to enquire about hang over’s, and it took two, frenetic weeks to fully blur the lines between musing, should you date your boss, to answering with a resounding, yes. Mutually, we set clear work place rules, determined to maintain professional standards, not conduct our fledgling relationship during company time. We endeavoured to maintain discretion and refrain from discussing details of our relationship with colleagues. We’d already abused the in-house email system, but now terminated all personal correspondence.

Clandestine affairs

Until we knew where our relationship was heading, we decided to keep ‘us’ secret. This was awkward, and super-sexy; so sexy that it became impossible to suppress public displays of affection – and office gossip. What was once fun rapidly became a source of anxiety; should I continue to deny it and play dumb? Eventually, I was asked by a friend/co-worker; are you and should you date your boss? I’d always been honest and open with my friend and was torn; I disliked having to dodge the question until I could ask my boss’s permission to reply.

Nothing that starts with deception ever ends well, and resentment now crept into this friendship and my relationship. Personal life and professional were merging and the balance was slipping in what I felt was his favour; I felt I was no longer his equal: I was now the subordinate in my own personal life, too.

To be continued… 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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