Flirting with Your Boss

Flirting with your boss is risky business.  Offices are notoriously gossipy environments and no one wants a reputation as someone who uses her looks and flirtation to succeed in the workplace.  Flirting with your boss can lead to favourable outcomes for you, however, and make otherwise dull work days a little more fun.  It’s natural to be attracted to people like your boss who are experienced, powerful, and well-respected.  But how you act on this attraction makes all the difference. 

Although you aren’t putting yourself at risk the same way a superior would flirting with an employee, you may still be contravening rules on sexual harassment.  Your boss might not be interested in your attentions and may actually feel insulted that you think he can be so easily manipulated.   Tread lightly and be alert for any signals that he’s uninterested: monosyllabic responses, avoiding eye contact, etc. or you may find you have date with human resources.  Familiarize yourself with the workplace’s sexual harassment and employee relationship policies.   

If you’re going to flirt with your boss, make sure that you look as attractive as possible without violating the dress code or any standards or workplace propriety.  Wear high heels if your work environment permits it.  You’ll look taller and slimmer and many people find them sexually appealing.  Don’t bite off more than you can chew, though, and stick to shoes that you can actually walk in, even if that means foregoing high heels altogether.  Get a new haircut, perfume, outfit, or piece of jewellery, as change attracts attention. 

Be subtle.  The point of flirting, after all, is to express your interest indirectly and to allow the other person to return or reject it indirectly.  It’s meant to be non-threatening and to allow all involved to save face.  Make eye contact with your boss and let your gaze linger slightly longer than necessary.  Smile whenever you see him.  If you like something he’s wearing, compliment it.  When he’s talking to you, touch him lightly on the hand or the arm.  If you shake hands, place you free hand on top of the hand that’s shaking yours.  If he asks you for special help or to stay late, do so.  He’ll remember what you did for him and maybe it will get you two alone. 

There are some important pitfalls to watch out for.  You may be tempted to toss your hair or tilt your head like you’re Lassie, but don’t.  Be sure to always behave in a professional manner, not like a ditz.  It may not be fair, but people will make negative inferences about your intelligence.  Even if you’re flirting with your boss to achieve some perceived benefit, do your job and do it well.  There’s no point in getting that promotion only to have people realize that you’re not qualified for the job.  When it comes to making physical contact with your boss, less is more.  You don’t want to make him uncomfortable or make tongues wag.  If you decide flirting with your boss is worth the risks, follow these guidelines and you should stay on your boss’ and human resources’ good sides.