It may feel awkward, but it's important to be certain that you are both on the same page before things go any further. If your flirting is unwelcome or excessive, you also run the risk of crossing the line from flirtation into sexual harassment, which in many offices can result in immediate termination.

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If they do not contribute to the conversation, start taking steps back, or start nodding more, you can understand that you are going off the track. If you are afraid to make these inquiries because you fear that people will gossip, remember that they will gossip even more if you get involved with your boss, so factor that into your decision.

Once you have the go-ahead signal from your boss at workplace, take the leap and enjoy the ride while it lasts. It might take between 3 and 13 soulful looks for your boss to realize that you are trying to signal attraction. The first thing that you need to do is ask yourself whether the boss that you are about to pursue is worth the risk or not.

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Remember: if it turns out you misread things and your boss is not interested, you will have a lot less to be embarrassed about from a straight-forward conversation than if you had attempted to kiss them, or worse. It seems like a simple piece of advice, but there are few things more appealing than a friendly, genuine smile. Relationships in the workplace, especially between supervisors and employees, are prohibited in many companies.By definition, it's hard to rehearse a genuine smile, but if you want to see what yours looks like, try thinking of something really funny and then looking in the mirror. Since there are so many possible risks, the best approach is to be very sensitive to any responses you might receive for your efforts, and subtle enough with your behavior that you can deny that flirting was your intention if it doesn't go off as planned.

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Lastly, you need to work on the traditional flirting methods to get the ball rolling for some hot pursuit of your boss. Finally, you might run the risk of losing your credibility or reputation for trustworthiness at work. Another way to flirt with your boss is to work in some casual touch, like offering a handshake and smile at the end of a meeting or giving your boss a brief touch on the forearm or shoulder when you’re chatting. One has to tread very carefully while setting down some romantic boundaries in a workplace environment.

A bit of casual flirting with your boss might attract just enough extra attention to land you that key assignment you were hoping for, or help you secure a more desirable shift. Your boss's answer to this should give you a pretty clear indication as to whether you should proceed or back off. Making and holding eye contact is the first lesson of Flirting 101, and is sometimes the only tool you need to convey your interest in another person.

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This article will walk you through assessing the risks, and then give you some tips for flirting with your boss, should you choose to proceed.Regardless of your reasons, it's important to know that flirting at work is a risky proposition, and must be handled with care.