How to Flirt With a Boss

People look for and find love in all sorts of places. Sometimes love is found in the workplace. In some cases, it's even found with someone in authority like a boss. While some people say that workplace romance with a boss is a sure recipe for disaster, there are plenty of others who say it can work. Here are some tips on how to flirt with a boss. You'll have to decide for yourself if a romantic relationship like this works for you.

Weigh the pros and cons of flirting with a boss. There's always a chance you could be putting your career at risk by flirting with your boss. Plus, embarrassment, misunderstandings and awkward situations are very real possibilities.

Engage the boss in friendly conversation as much as possible. Flirting doesn't have to be the stereotypical giggling and hair tossing for girls and macho posturing for guys.

Use your body language to let your boss know that you are comfortable and confident with yourself. Meet eye contact and smile often. Genuine smiles are better than creepy, fake ones.

Be available to help out your boss professionally whenever you can. This lets you cross paths more often and gives you more of a chance to read body language to see if the interest is mutual.

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  • Let your instincts guide you.
  • Know your company's policy on office dating and office romance.
  • Be discreet.


  • Be aware that flirting with the boss could damage your reputation at work through gossip and rumors.
  • Be cautious about flirting with bosses who have a reputation of taking advantage of subordinates.
  • Don't stare and keep your hands to yourself. Occasionally it's okay to touch your boss's arm between the wrist and elbow if you're flirting with him.

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