She’s Your Boss & She’s Just Hit on You. Here’s What To Do Next…

Hey guys,

A lot of men have this fantasy of being the object of desire of their lady boss. It could be that reverse 50 Shades of Grey effect; when men like women who are on top, when men like being dominated by women who know what they want and who know how to get what they want.

Just because I’m a stand up comedian doesn’t mean I don’t have the same fantasy. Though mine is more likely to be one of the events managers in one of the theatres I gig at in  New York, Los Angeles, or Lousiana.

But when this ‘fantasy’ actually comes to life, do you know what to do? After all, it could get awkward. You can’t just get into it and expect to still have a job the next day (when the bigger boss hates you for screwing with the smaller boss) or at least, expect to go to work without getting hated by your colleagues because of the insurmountable advantage you have over all of them career-wise which you would have earned in quite an ‘unfair’ manner. It’s not like it’s going to be as easy or as magical as ‘The Proposal’. And even in a rom-com perfection, Ryan Reynolds’ character didn’t exactly have it that easily anyway.

Tips for You

SO should you find yourself in this good-bad-awkward situation, here’s a little something of a tip on what to do, you handsome you.

Number one, don’t go about spreading the news to the entire office. Seriously, that’s going to win you more enemies and fake friends than real ones. It would make you popular, yes, but in a bad way. Let them notice it on their own.

And remember where you are. You have to always be professional at your workplace. Don’t take advantage of her flirtatious advances on you to skip work or get a raise or whatever. In fact, don’t flirt back when you’re in the office. That, or at least don’t do it too openly. You should click here for some rather good “alpha male” tactics.

Always treat her like your boss, because she is. Just because she likes you, or at least is hitting on you, does not necessarily mean you are superior over her. Boy, oh boy, your salary still depends on her and your work for her. So, yeah, she’s your boss when you’re in the office no matter what you do together past working hours.

Don’t make her give you any special attention or grant you special favors in exchange of whatever she wants. Whether she’s looking for sex, flirting, escort services from you, don’t use it as leverage for your job. That is unfair and outright low. She, or anyone else in knowledge of whatever you have, will not respect you the way you want if you play your cards that way.

Whatever you do, don’t play games with her. No matter how impersonal you get, or how impersonal you both pretend to be, emotions will eventually come into play and could dangerously affect your work and the entire workplace.

Oh and if you don’t like her, politely decline her. She’s your boss, she could fire you. Seriously. Apart from the fact that she’s your boss, she’s also a woman and that fact alone deserves a respectful, polite rejection.

Lastly, sorry about this but expect tons of awkwardness. It will be awkward mostly for you; this is likely not the first time for her to hit on an employee or subordinate.

If you do want to impress her though without saying anything; read more here.

Good luck you handsome you. *Wink*

P.S. Don’t forget to attend my upcoming standup comedy show: